Theory: Two Sides of the Same Coin (or Taking a Page from Hooking Up and Applying it to Dating)

Consistency is important for shaping not only who you are but also for keeping you sane. Too many exceptions and “what if” scenarios will drive you batty and make it so that your standards don’t mean anything. There is a time and place for exceptions, though if you’re making too many it’s not necessarily the behaviour that needs to be changed, sometimes it is the standards you hold yourself to.

I’ve said before that you can’t apply rules to dating anymore, though there are certainly best practices you can follow. For a long time I’ve been operating under two different sets of practices when it comes to men and I don’t think I realized this until recently. When you take stock of your behaviours, you don’t only notice the good and bad, but the inconsistencies stand out too.

I always treat dating and hooking up like they are two completely different domains, forgetting that they are two sides of the same coin. They aren’t exactly the same – don’t get me wrong, but they are more similar worlds than we sometimes think. The same problems arise and the same triumphs arise and the same results occur and the same feelings are generated regardless if I’m left looking at heads or tails. The way I react to things is different depending on which side of the coin I’m on. Things that don’t bother me with hookups – for instance, not hearing back from a contact I’ve initiated or seeing a guy once and never again (in most cases anyway) – are things that I take much more to heart in the sphere of dating.

This makes no sense because for a long time dating and hooking up had the same end goal in my life. (Okay, they still do in some regards) That is of course, finding a partner.

If the ultimate desired end for both dating and hookup scenarios was finding love then I should be reacting the same in both guises when things happen. It shouldn’t hurt less or more to find myself unwanted depending on the category heading, right? Nevertheless, I always wind up more hurt when it comes to the notion of dating, even if I can experience the same thing with a hookup and register nothing.

As you know, I’m no emotional superhero but when I took stock of my behaviours surrounding worst-case scenarios in dating and hooking up I found there were distinct differences and finally started questioning why this was. The simple truth is that I don’t know why I feel so different depending on the category heading. If I took a few pages from how I react to hookups I would actually feel less stress and I would feel happier. For most of my life I’ve been my own worst enemy when it comes to dating and I always assume the worst and that’s a big part of it. It shouldn’t be a surprise that I take the small failures to heart. I’ve always felt much more confidence and control over my sex life than my dating life.

When people I’ve shared a bed with don’t contact me back and it’s not a big deal but I feel pangs when what seemed like a potential romance goes by the wayside before we could meet face-to-face, something isn’t right.

I’ve already started training myself to stop keeping these worlds so separate. Even though it’s impossible to merge the two completely, I’m trying to actively bridge the less affected way I feel in hookup scenarios with their counterparts in the dating world. It’s not an effort to try and become hardened or unemotional – it’s simply trying to beat myself up less often.

1.       The fifteen minute rule: Nobody takes forever to make a move if they’re interested.

The fifteen minute rule is simple (and yes this is a rule) – it’s not based on hard science, just observation. The rule is that if I get in touch with a guy about hooking up he has a fifteen minute window during our back-and-forth contacts to further the conversation and show interest. If not, I assume he is not interested and I move on.

Fifteen minutes might seem arbitrary, but before I offer you any rationalizations, I must stress to you that this is the way it always happens for me. When I started taking notice, interested guys never took longer than fifteen minutes to make a move. It’s not buying a certified pre-owned car – you don’t need a good night’s sleep to make a decision about whether you are going forward or not. By virtue of looking, you know what you’d like to do, right? It’s more like choosing a meal from a restaurant menu, you know you’re hungry you just need to select something to satisfy your appetite.

Deviations from this rule are rare. Even if you’re only checking your  email or dating site inbox every few minutes you will have seen what the person wrote to you within fifteen minutes. It’s enough time for a person to come to a conclusion and it’s not an unreasonably short amount of time to make a decision. I’ve said before that very few people write back if they aren’t interested and that is almost exclusively what happens if their interest is no longer piqued.

The exceptions for this rule are few and they are always outliers – the guy passed out for instance and writes you the next morning, or his roommate came home and she is drunk and he has to take care of her or he got a phone call that he had to take which made him late in responding.

Generally though, once fifteen minutes pass, you know exactly what’s happening: nothing. Whereas in dating things can be very drawn out, hooking up involves a much swifter process. You know your fate in a much more timely manner.

I’ve never found myself truly bothered by having fifteen minutes and one second come along and finding that a guy has disappeared. In dating however, I get more upset when a guy disappears even if we barely have a history together. I start thinking that my dating life is doomed and that I’ll always be alone, yet I’ve never had someone break the fifteen minute rule where I proclaimed “Well, that’s it! There goes my sex life forever!”

2.       Most people don’t want to get with most people so don’t take it personally.

There are plenty of fish in the sea but this doesn’t mean you’re going to want most of them. Generally we are only looking for smaller, targeted groups of people and that doesn’t mean that there’s anything wrong with those who exist outside of that core. They are simply less of a match for us. Most people we will ever encounter will not be a match for us and, conversely, we will not be a match for most of the people we meet. Life is too short to take this to heart.

I think it helps to put it in a numerical example. Let’s pretend that you put me in a room with 100 men and charged me with the task of choosing the one who I most wanted to sleep with. Let’s say I walked in and discovered that 50 of them were between 20-35 and 50 of them were between 35-50. We will make no further specific distinctions but will assume that of these men we have variance in height, weight, physical stature, physical attractiveness, ethnicity, personality and so forth.

The reason I chose this type of sample is because over time I have heard from people all over that spectrum – my specifically outlined preferences be damned.

Unless there are some real outliers we could first count out the over 35 crowd. My 100 is now 50. Then, let’s add in three other criteria: physical attraction, sexual attitudes and preferences, displayed intellect. Men would begin dropping like flies. The truth is I would never really be selecting from 100, I’d be selecting from a smaller pool and that’s what I do when I hookup and when I date.

In my experience online – seeking dating or hookups –I’ve been contacted by a lot of people who have been very far removed from my physical type, sexual attitudes and preferences, age limits, physical location… You name it! It’s part of the game though and generally you just shrug and move on.

If I had an actual number of people I’ve contacted and who have contacted me the number would be terrifying. If we looked at the number who contacted me back and who I contacted back it gets (mercifully) smaller. If you look at the number where anything came of it – it is even more miniscule. If you were to profile these people you would notice, that, with few exceptions most of them fit into a certain type.

This can be easy to brush off when it’s hookup-related but I always feel worse when I don’t hear back when it’s in a dating scenario. I think part of it was feeling that a hookup didn’t care about my personality so it wasn’t anything to take personal. But when you actually think about it, a guy on a dating site only has a tiny bit more insight to my personality. If he’s not going for me – I shouldn’t be taking it to heart. It doesn’t make you any less of a person because you’re not everyone’s type – you’re in good company with the other 99 out of 100.

3.-The spectrum of preferences is not simply “you’re attractive” or “you’re not.” People have preferences that have nothing to do with appearance that can derail plans of a future.

For a long time I assumed that if I wasn’t getting anywhere in dating or if I wasn’t finding success hooking up that the reason was simple: I wasn’t attractive enough. I couldn’t possibly think of any other reason why this could be. What other alternative could exist?

When I went on my blind date several weeks ago the guy was, for all intents and purposes, attractive. He was the kind of guy, frankly, who made me wonder why he was having such difficulties dating. A petite, slender fellow with a foreign background, one would surmise, would prove quite a catch. After getting to know him though, I had a better grasp as to why he was single. I didn’t find him very interesting and though I’m sure someone exists for him out there, I could see how many men might find him not meeting their tastes.

In a prior entry I talked about several instances where I met handsome guys but found myself not interested based on less superficial qualities. Even if someone is attractive it still doesn’t necessarily mean that you’ll want to date them.

In dating, I have not solely ruled with one stamp that said attractive and one that said unattractive and furiously pounded as needed. I decided to think about a few things that have turned me off of dating or a hookup that don’t include physical attraction. Here are five that came to mind:

1. An incoherent online profile full of grammar and spelling mistakes
2. Evidence of bedroom interests – fetishes or whatnot – that I have no desire to explore
3. Incongruence of basic intimate and sexual desires
4. Uncomfortably self-deprecating humour or statements like “I’m socially awkward” or “I’m a really simple guy.”
5. Guys who can’t seem to follow simple directions (ex: If I ask for stats and a photo and you send neither, I will have misgivings about you)

Please note that none of these have to do with looks and some of the people who have fallen into these categories, sadly, have been real lookers.

A guy once told me that I wasn’t his type and as you correctly assume I was immediately horrified. My horror dissipated almost immediately however as it turns out this person preferred men of colour. I’m white. I was surprised because usually, in my world, “you’re not my type” means “you’re too fat for me.” There have been a few times where it has been (that I know for sure) and there have been many times when I simply assume that it has been the reason. The more I thought about it, I realized that yes it could be that, but it could also be any number of reasons.

It’s a broad spectrum out there as to why we show preferences to some people over others. It’s not simply attractive or ugly and that’s that. It’s easier to focus on what we don’t like about ourselves and to make that the reason. That’s why for so many years I said it was a weight thing. Despite the fact that I’ve hooked up with some really cute guys and gone on a few dates with really cute guys, I kept telling myself that was the sole reason. There was no other reason they couldn’t be interested in me.

The truth comes from my own behaviours – there is a whole host of reasons why I haven’t gotten back to people or continued on with people and looks haven’t been the paramount dealbreaker. Instead of plain black and white, the reasons are more like a paint display at the hardware store.

*

Not long ago, I went on a date with a handsome thirty year old. I picked a quaint bar just off St-Laurent that brews their own beer and we spent a very pleasant evening together. Originally, we were supposed to hook up. We had exchanged several emails and for whatever reason this guy threw in the gamechanging suggestion that we should get together for a drink. It wasn’t one of those “I want to meet you and then we’ll see where this goes,” kind of drinks. It turned out to be a date.

It was a Sunday night and the bar was quiet. I ordered a few black cherry beers and wore my first date outfit and crossed something off my bucket list when I spoke competent French with him for a large chunk of the evening. We talked liberally about our lives in a way that you can only do when you already know each other’s sexual inclinations.

He had an interest in entrepreneurship and he was well-travelled and had a professional career but was feeling the need for a change. We talked about his family back in Europe and how he came out late (as did I) and comfortably navigated sex as a conversation topic. We laughed a lot. We smiled a lot. He made a point of asking if I was single. Though we had a nice connection, subsequently, nothing came of our evening – romantic or otherwise.

As I shrugged it off, I realized that there was something a bit different. He’d muddied the waters by straddling both the hookup and dating categories. Normally at the end of a date that went well where nothing came of it, I’d feel a loss, but since we were supposed to hookup it didn’t count as a date. Even though it was. For someone who has noticeably different feelings depending on the category the distinction was no longer crystal clear. If we’d met, say, on OKCupid and the word dating had been present the entire time, it’s safe to say I would have felt upset. It is only because the wording was changed that this didn’t bother me.

It felt healthy to move on so easily and not to proclaim my dating life over. Though part of me wishes this was simply maturity, I know that if we’d always talked of dating, that I would not have been so unaffected.

Part of me knows now, though, that it’s not going to feel like that always.

Sex Stories I Never Even Wrote

Not every man from my past merits a tale. I know this is probably hard for you to digest, but it’s the truth. There are myriad reasons why this is true and when I was working at my last job one of those men turned into a story – it’s difficult to wait on someone who once proposed a three-way to you and not to have it become a story.

We were supposed to hook up – on several occasions, but it never came to fruition. Almost two years later we found ourselves faced with each other in a completely different setting. One where all I could do was drop a few veiled hints and curiously watch for even the slightest glimmer of recognition. It reminded me of another time when I ran into someone who wanted me, but had never even seen my face. I wondered if he’d give me the time of day in real life – faced with an actual man instead of a wispy description of facts.

*

One thing that sucks (and there are many things that suck) about meeting guys online is that sometimes even after you go through all the vetting processes and decide that you want to get together, something gets in the way and you never try again. Or you try again and you fail again. You go looking for new strangers instead of trying to work things out with the devil you know.

It’s kind of like going to the grocery store and seeing something you like and meaning to take it home but it slips your mind somewhere in aisle four. By the time you get home and unpack your groceries and sit down with a cup of coffee you’re like “Shit, I wanted to buy that” and you shrug it off and make do with what you have. Or you find some sort of substitute.

In short, it kind of sucks that it doesn’t happen but you get over it quickly. You make do. You don’t think about it again.

*

I’m talking about very specific cases – not the kind where the other guy flakes on you and doesn’t give warning. (It’s happened) Or the kind where bicuriousity suddenly disappears once the other guy realizes the gravity of having another erection in the room. (It’s happened) I don’t mean that one time I got lied to about the guy’s age and appearance and pretended that nerves got the best of me and left but really I was just grossed out. Then every time I saw him at the gym – because of course it turned out we would go to the same gym – I would roll my eyes as I passed him and think “maybe in dog years.” (It’s happened)

I’m referring to the ones where they fell asleep in the middle of emailing or we took way too long doing so and neither of us had the ambition to get together anymore. We said we’d get in touch later and never did. The times when their roommate comes home and they can’t leave now, or have a guest. Where something comes up at work and they can’t any more. When they propose meeting another night because they have too much studying to do – or an early morning the next day.

Once, a fellow and I tried to figure something out for months but never sealed the deal because of endless scheduling conflicts. Then there was another guy who I heard from infrequently for about two years. Every few months, he’d drop a line, or I’d drop a line and we’d always respond but it never got any further than that.

There are better things to dedicate your mind to than thoughts of what could have been and so you forget. If you can’t think this way about the ones you were intimate with, you certainly can’t think this way about the ones who never even made it that far. This is difficult to do when you realize how small the world is and find them standing right before you. It’s interesting to offer customer service to someone when you have at length discussed offering other services to each other and you don’t know if he has any idea who you are.

*

When I was living in my small town there was one guy who sent me lots of messages about getting together to hook up, but he never even saw my face. To him I will always remain a stranger for as much as he wanted me, he never saw me and formed his desires based on a loose sketch of details from a thinly filled out dating profile.

Though much of that time period was a wasteland insofar as pleasures of the flesh, I simply wasn’t interested in his proposition. The marketplace for gentleman in my hometown was not exactly thriving and, speaking frankly, given the options I had, celibacy was often the most attractive one.

This guy was looking for dating according to his profile, but the messages he sent were less wholesome. Neither his written profile nor his pictures nor his messages enticed me enough to go for it. He seemed (from the profile) like a good-natured, downhome kind of guy. That couldn’t be farther from my fantasies. Back home there needed to be an extra little shove to go for it, and he lacked the sort of force I needed.

I did the polite thing and never answered. I think it is a far worse evil to say no thanks to someone when they propose hooking up. There’s no implicit need to communicate that you aren’t that attracted to them. They’ll get the hint.

I heard from him again though.

And again.

And again.

Finally I told him flatly that I wasn’t interested – not in a rude way, but a succinct one. Now he could move on. There were few enough men on that site that it wouldn’t be hard to remember that efforts on me were wasted. There were other fish in the sea to try and reel in.

*

If it sounds cruel, perhaps it helps if I admit that I had a tally like that for myself too. Not every guy was interested in me, just as I was not interested in every guy. I had some on my “don’t contact again” list where the interest only came from my side. Unlike so many men I’ve dealt with elsewhere, in my hometown they seemed to have a problem remembering what earth they salted and could no longer plant in. One guy in particular made a rude comment about my size and then I promptly stopped talking to him. He kept messaging me and I took a great pleasure in ignoring his contacts. And an even greater pleasure reminding him what he had said and how uninterested I was in hearing from him after the messages became incessant. And then doing so again when he kept doing it anyway like a fucking idiot.

The downhome character kept on going too. I would receive his offers late at night on weekends, at times when many people would be drunk, but usually I was at home watching SNL with Chinese food. His diction and boldness suggested he was not having a quiet night in. Surely he would be too shy to speak such graphic things out loud.

His messages were rank with desperation – the kind of desperation that I publically abhor, but often fall victim to after a few drinks, if truth be told.

I had to remind him again that I wasn’t interested for he got far too communicative. Eventually he took the hint, but kept on trying well past the point where it was a prudent action.

*

I saw him once out on the town. I had been drinking and I remember seeing him and immediately knowing that I’d made the right call. He stirred nothing in me still. I think he was too much of a hometown reality for me to face. I wanted to find someone who, like me, didn’t exactly belong here. Someone who reminded me of late summer nights in Montreal or Cambridge.

I decided to make conversation with him – not to be a dick or let him know who I was or what I’d said or what he’d said, but I wanted to see how he’d react to me. Without even seeing me he had made overtures – fierce ones, committed ones – and he was a single man. One who wanted a relationship to boot. What would he do now with me in the flesh before him?

Not very much, actually.

He couldn’t have been anymore aloof or disengaged. There was not a twinkle in his eye or droplet of interest during our brief chat. He barely even looked at me. I quietly excused myself from our conversation after realizing that there wasn’t much of one going on. He offered no protest.

*

I was quick to note that the guy at work looked familiar. As most of our clientele were women, male clientele always stood out. Particularly ones who it seemed were gay. I couldn’t immediately place this fellow, all I knew is that he was relevant somehow. I thought it might be my imagination running wild, but then one of the people he was with called him by name. That brought it all back to me. I tried not to blush.

He was one of those types who liked to send emails with his personal email, not some hookup pseudonym, meaning that with a quick copy and paste I was able to view him on Facebook. You might think that sounds like creeping, but to bastardize a Mo’Nique quote it’s not called creeping in online dating, it’s called motherfucking survival.

*

I’d received several emails from him over time based on an ad I’d posted and after seeing the attached picture I thought he was out of my league. In my books he was quite fetching – too fetching actually – and as such, initially I never wrote back. When I noticed that he kept responding each time I posted, I decided to write him back. When I didn’t hear back from him I assumed that my initial instincts were correct.

A few months later, he wrote me again and I responded again, but this time it took. We got to talking and decided to get together, but then we kept running into issues. He worked really odd hours so I’d get emails from him while I was sleeping. I’d respond and then he would be sleeping or working. This carried on for days. We could never sync. Eventually our conversation trailed off, only to reignite a few months later. Again it came to nothing; that was that. I moved the next month to Nova Scotia. Despite the interest and despite our intentions we never hooked up.

*

I must disclose that I might have tried harder with him if it had not been for what I’d seen on Facebook. Eventually, when I thought to look at his profile I noticed that he was cute, but he wasn’t exactly what his photos made him out to be. He was hiding the fact he was a little chubby with camera angles. Seeing him front on I realized he was missing the more chiseled features I’d found myself drawn to. I think it was a little weird to realize that he was a little too achievable looks-wise to try and evade my grasp at first. Between that and the sheer effort that was required to land him, you can understand why I moved on.

He stood before me now – cute, but still achievable. The kind of guy who I wouldn’t be averse to meeting for such purposes. The kind who, physically speaking, I could date. He was in the store with a female friend and his mother. He was outfitting a new place and quickly showed the stripes of a whiny diva who I tired of quickly.

When I offered him assistance and was met with condescension I wanted nothing more than to roll my eyes and remind him that he was being pretty uppity for a guy who once wanted to blow me.

In our lengthy email conversation he did indeed suggest a three way, but that’s not really my style. I evasively said that there weren’t any potential candidates when really it was more of an unwillingness to share on my part and little else.

*

It was weird to see both of these men in different environments. The one from my hometown, had things worked in his favour would surely have been wide-eyed to see me. The same with the guy who came into my workplace.

Removed from that bit of reverie and from the context of sex neither of them gave me a second glance. While, it didn’t change my mind about the hometown guy, seeing the other one bitch and moan as he shopped, with his mother nonetheless, certainly showed me that it all would have been merely fantasy. The reality was he wasn’t the kind of guy I’d be interested in dating – cute or not.

It made me wonder if so much of my sex life has been just as fictional. The ones who looked at me with lust in their eyes, would they do it again, or were they just doing it because that’s what we planned?  Would I turn their head if I walked by them on the street? If I saw even the ones who seemed most fascinating in a more real moment would I still find myself interested? Were the moments we shared always real, or did we just get a bit caught up in fun and games?

I don’t know if the guy who came to work is still single, but I do know the other was. I also know that both of them had a single gay man acting interested in them and they both pissed the opportunity away. If I was interested, I’d probably be the sort of guy downhome was looking for and if the guy who came to work had any sort of photographic memory, he’d know that I was a sure thing to bed, or at least, for him, I once was. I doubt he recognized me, though once I almost thought I saw a glimmer of recognition. I had located a product for him and he was actually kind of happy about it.

I mentioned that it was my job to please him and looked at him blankly, allowing him an opportunity to press further if he was so inclined.

Somewhere Only We Know

You’ll have to excuse my absence for I’ve been a bit distracted.

I wrote the following in a recent entry:

It would be nice someday to meet a guy who is going to stick around for the long haul – one who I won’t write about. While I’ll surely gush about our relationship with my friends, our world will be our own and the details won’t appear in print. It’s one thing to talk about the Colins and the Dereks and the Patricks – the Sebastians even – but someday, I hope there will be someone who wants to stick around and won’t merit a chapter among all those characters.

I met someone last week who seemed like he might be that guy, we’ll call this exception to the rule Brian.* I told some friends about him – I gushed. I had to reason to gush actually, because it seemed as though he was different and it seemed as though he found me equally beguiling.

I’m writing about him though, so I suppose you see where the story begins and ends.

The story didn’t begin or end as planned.

Though it wasn’t a linear path to get there, we’ve arrived at a common conclusion. We’re going to see where things go and we’re going to take our time doing so.

For the instant, our world is our own and I couldn’t be happier about this development.

Protected: Late Nights Playing Pretend in Montreal (Part Two)

This post is password protected. To view it please enter your password below:

Password:

Protected: Late Nights Playing Pretend in Montreal (Part One)

This post is password protected. To view it please enter your password below:

Password:

Dilemmas or “The Prelude to Fenway, Etc.” (Part Two)

In January 2009 my vantage point on life and love was a lot different than it was when I first actively tested the waters of being gay. I was now living in Montreal’s West Island and over the previous year I’d started to ask difficult questions about my sexuality and I’d fallen in love and had my heartbroken because he didn’t feel the same.

I never got to kiss the guy, though I fantasized about it. We never hooked up, though the idea of doing so made me melt. I gave him my heart though and he didn’t want it and he didn’t want to talk about the gift I offered him. He wanted me as a friend and I wanted him as a lover and it seemed, as we spent time together that we imagined that each other was what we wanted, but didn’t realize that our visions of each other didn’t mesh. He thought I was a friend because I stuck around. I thought he loved me because he stuck around. In short, it was a mess for both of us and we should have stopped trying to be friends long before we finally did. If I didn’t know better, I’d swear we were both terrible masochists and we just kept pushing forward because we wanted to fuck things up for ourselves.

That experience was sufficient enough to make me want to figure out how much truth there was to the urges I had. The guy I’d been with that one fleeting time did nothing for me. But, in falling in love, a new answer emerged for a question I thought I’d known the answer to.

I never imagined myself falling in love with another guy – but then I did and I really had to start reevaluating my supposed heterosexuality or, perhaps, bisexuality. I could want a guy to cuddle with me and to do something special for me on Valentine’s Day and spend lazy Saturday mornings in bed with me. It wasn’t beyond me.

Though I had been in love with the guy, it was only insofar as one can be when they’ve never been loved reciprocally in a relationship with someone. I wanted to be intimate with him but only insofar as my mind created awesome fantasies that might not mesh up with reality.

Reality so far hadn’t meshed with my fantasies. What if being gay was just some daydream that I hated in practice but liked in theory – like how I assumed red wine would be amazing but then I bought some during my salad days at college and thought it was disgusting.

Most of the first bottle I ever bought went in the sink.

*

Montreal had a lot to offer someone like me – lots of anonymous people with whom I could ask questions through actions rather than conversation – but, even given this cloak of discretion and anonymity I still had to allow myself to go ahead and play.

There was a guy – Max*, we’ll call him – who I got to talking to over Craigslist. He was also from the West Island and, like too many of my stories it seems, was friendly at first but eventually became flirtatious. This was a surprise to me because he was for all intents and purposes straight and in a relationship with a woman. (Of course, he was from Strictly Platonic where nothing is ever as such as we’ve learned.)

I didn’t say anything about the overtures at first. Eventually he admitted to me that he was curious about guys and wanted to know what it would be like to be with one. I hadn’t yet mentioned my sexual preferences to Max, simply never allowed the subject to come up.

One day it finally did – he wanted to know why I didn’t mind all his overtures. I told him that we were both on the same page and it was settled. We were going to get together. And soon. He said that he didn’t see what was so terrible about two attractive guys (his words, I swear) exploring with each other for the first time. He wanted to come over to my place and spend the night and he mentioned different scenarios in which we might find ourselves together. I was unbelievably excited but also absolutely terrified.

Part of it, honestly, was that I was scared of the notion that someone wanted to be with me so intimately because I felt fat. I didn’t feel sexy at all. The type of intimacy he was describing was pretty heavy and pretty naked and pretty revealing. I had never envisioned my body being privy to such discovery. The body that was, was a fiction – some thinner version of me in a nebulous future place and time.

I wasn’t sure how to understand myself as a sexual person still. I was so uncomfortable with myself that it was hard to embrace the fact that I wanted to jump his bones really badly. I wasn’t even sure I could articulate that without feeling dirty or embarrassed.

A few days before he was to come over I had a change of heart and told him I couldn’t. My reasoning was that I wanted to get to know him in a nonsexual way first. I remember saying to myself that I couldn’t be that type of guy to meet with strangers and have sex with them right away. (My vantage point changed, obviously, and that shut me the fuck up.) I also had to know something from him. I wanted to know if, should he enjoy himself and want more, if there could be a future for us as a couple.

Part of me cringes because I asked that of him, but sex and dating was all new to me and, having gone through an experience where I cared deeply for someone and could never figure out what he truly felt for me, it was essential that I was careful with my expectations and my fragile heart. I wanted confirmation that if things went well that I wasn’t going to have to play second fiddle. I didn’t want to be some secret. He had a girlfriend and as far as I saw it we were both confused and we both wanted to experiment and that wasn’t the end of the world. If he didn’t experiment with me, it would be with someone else and vice versa. Things were going really well and I had this fear that if we hooked up that we’d both really like it and then he would see me in secret and that the girlfriend would get all the splendour and I would get a little bit of fulfillment but a lot more heartbreak. Also I would be a homewrecker, a whore.

Naturally he couldn’t promise me anything definite, but he said that he was open to seeing how things went and that he wouldn’t rule anything out just yet.

We never did end up getting together. Our talk was nothing more than talk. After our plans were nixed he disappeared for about a week. When he returned I mentioned to him that I had assumed that he’d been mad with me. He said that he was ill and that he hadn’t been around his computer. Then he got furious with me for thinking he’d act like that. It turned into a spat and I figured it wouldn’t be a big deal.

The next time we talked he couldn’t stop bringing it up and being rude to me. Between that and some of the red flags that had popped up I did one of the most difficult things you can imagine for a guy like me. I removed him from my MSN list and moved on from a handsome and willing guy who wanted to bed and possibly date me.

*

Instead of with Max, my first big city assertion of sexuality ended up being with that girl who took me home from that party. I did feel on some level that I needed to be with a woman because given what had happened with that first guy I wasn’t totally convinced that being gay was the road for me. I also knew that all my life I said that sex with a woman was probably going to be a sort of necessary evil if I were ever to get a girlfriend or wife. It seemed as though in the path to self-discovery, it would be a secondary evil there as well.

I will admit that my need to be with a woman, after falling in love with a man had changed somewhat, but I still had to know. I had been in love with one man and attracted to plenty of girls and I’d been with one man and was pretty nonplussed by what I’d seen so far. Maybe it was a fluke. Maybe I was just royally confused.

As a man who was – ostensibly – straight I had endured many snide comments and insinuations and had been made to feel like a loser for not having been with a woman sooner. I jumped at the chance and felt a lot of pressure because I just wanted all of that and, hopefully, a lot of the confusion to stop.

Being with her clarified nothing. Part of me wanted nothing more than to be so repulsed that I would run away. That never happened.

It was confusing because I didn’t not like it, but I didn’t care for it much either. To this day I describe how for me being intimate with a woman is like eating Ethiopian food. I tried it once. It was okay, I suppose. I wouldn’t give a glowing recommendation of it to my friends. It isn’t something I feel compelled to try again, though, if I were really, really desperate and had absolutely no other option – like living on a desert island and it was this or nothing – I suppose I could, though I can’t say I’d be overly enthusiastic to.

After what happened with her – when I had one of each in the bag and realized that I wasn’t entirely sold on either, I was just as scared as I was relieved that I finally had some evidence to work with. The answer was still ambiguous. I told myself that I was now free to do whatever with whomever though I also wondered if maybe I was asexual – maybe I just wasn’t that into sex at all. It would have explained a lot.

*

There were two fleeting encounters after her that didn’t further elucidate anything. They were both men and both hands-off and wholly unemotional and I still wasn’t as into it as I had wanted to be. I thought maybe I needed to be in love to enjoy being intimate with someone and so I tried to find someone to love, but that didn’t work out either.

There was one more hookup the night before I left for my first summer in Boston. He’d actually answered an ad that I’d put up a while before and forgot about. I remember I knew it was going to be different because when he wrote back to me he mentioned his personal interests and this caused me to think about him more as an actual person than just some means to an end. He was younger than me and cute and though I really just wanted to go to bed – he was much more my type than anyone else I’d been with to this point. I was willing to sacrifice some sleep to see what could happen between us. Getting into Boston a few hours later wouldn’t be the end of the world.

We met at the Orange Julep off Decarie and then went somewhere dark and quiet. We didn’t just jump right into things – we talked for a while first.

I’d never really talked about sex with a guy before in that kind of way. We both had confusion on certain levels and it was a comfort to know that I wasn’t alone in that. We talked about other things besides sex too. He even mentioned about how he was considering auditioning for a porno and I remember thinking how funny it would be to one day see him getting fucked in a banner ad.

After we talked, we both played the “what do you want to do?” game and kept asking each other that infernal question. He proposed an Orange Julep of all things and prattled on about the secret recipe. Whereas before I had always entered into a hookup silently and hadn’t voiced an opinion good, bad or indifferent, I plainly told him what I wanted to do.

And then we did just that.

Finally, I could say without reservation that I enjoyed the experience. That was an enormous relief for me – a real weight off my shoulders that made driving off to Boston the next day a little lighter.

As you well know, a week later in some guy’s apartment in the Fenway all the stars finally aligned and I had a clearer understanding of what I enjoyed and what I longed for. It was honestly, at the risk of sounding hokey, like being reborn.

*

It’s been weird to write this pair of entries, but it’s also honest because I can’t pretend that the road to understanding myself was simple and linear. It hasn’t been, in any facet, let alone sex and sexuality. Some people assume that I’ve spent much of my life putting up some false front and that the whole time I knew I was gay and I just wasn’t ready to come out for whatever reason. I have carried around an assortment of mismatched baggage all these years – some of which has been blessedly left behind, but other pieces linger, small fanny pack or jumbo suitcase depending.

I can’t say that the first few experiences I had were 100% ideal, but they served their purpose. The only time I ever regretted some of my choices in partners was after Patrick as I paced around the Plateau that grey Saturday morn. I told myself that if it could all have been as amazing as it was with him then I would have been so blessed and so lucky. That there were others who never came close at all was a tragedy. It was a real shame that my whole sex life couldn’t have been that special.

There are people who I barely remember – not because of alcohol or blunt head trauma – but because the encounter was so fleeting that it barely registered. So unmemorable that it takes great effort to call them to mind again. Ideally we wouldn’t have to deal with this – we’d find the perfect person right away and spend our lives with them and avoid so much hassle and heartbreak and stress. We would never want for anything with them. We would also avoid asking questions. We would miss out on a lot of valuable answers.

That’s not life, for better and for worse. You have to fail and fuck everything up and be confused and ask questions and sometimes not find the answer right away. Sometimes you have to find the wrong answer first. If you finally find the right one you need to hoist your answer in the air like the Stanley Cup and be proud of yourself.

For so many years I thought if life didn’t roll out perfectly then something was wrong. If everything wasn’t perfect then the person was a failure. I’ve since learned that the most comfortable and interesting and sensible people have had these qualities coloured by life experience. If I had waited for 100% perfection – of my body, of my self-esteem, of my sexual identity – I don’t know what my life would be like today except that it would have passed me by. I would be very sexually frustrated for one thing and I wouldn’t have learned a damn thing about myself along the way.

*Not his real name

Dilemmas or “The Prelude to Fenway, Etc.” (Part One)

A complicated topic that I can’t bite off all at once involves a question that I get asked quite frequently. “Did you always know you were gay?” The answer is no, I didn’t.

No.

Seriously.

I didn’t.

Many people find this surprising, but it’s the truth. That doesn’t mean, however, that it’s an easy answer that accurately reflects how I felt for many years.

Now if you posed the question, “Have you always been sexually attracted to men?” the answer would be yes, but even then there would be a caveat. While I was sexually attracted to men, I wasn’t attracted to them in the same way I was attracted to women. While women were turning my head on a daily basis, I wasn’t seeing the same kind of beauty in men. Yet, nevertheless, girls weren’t where my horny teenage mind wandered.

I wanted to both emulate certain types of guys in behaviour and looks and suave attitude as well as be sexually (but not emotionally) intimate with them – at least in theory I did. Since I didn’t want to give them flowers or kiss them or have them bestow me with pet names or marry me or anything, I always thought it was safe to assume that I wasn’t gay. Maybe curious. Maybe just a guy who enjoyed fantasizing about other guys. Maybe some sort of bisexual at the very most. But not gay. Never gay.

One thing that is both a blessing and a curse for sexually confused young men is the bevy of information out there that draws the distinction between gay acts and homosexuality. The insistence is that bedding a man doesn’t mean you’re gay – the act is gay but it doesn’t mean you are gay. Now when romance and wanting to partner with a man, things change, certainly, but as long as it’s just sex, you’re just full of hormones, or curious or something else that means you’re not gay. At least, that’s how I read into it.

When sex comes together with romance and wanting to partner with a man the difference comes in and I didn’t understand or want any of the romantic stuff until I was in my twenties. When it came to women, I found them attractive and I had romantic feelings towards them and this was enough to make me avoid calling the question about whether or not I was gay. Inever gave women much thought sexually. Just a shrug, really. I figured that eventually I would end up with a woman and I’d be fine having sex with her. Though even then, I didn’t imagine it would be often. One might say, even, that I didn’t imagine that part at all.

*

I was young though, that’s what happens.  According to everything that I understood from my worldview I wasn’t gay. And this wouldn’t change for a long time – until my worldview changed, a process that rarely comes easily.

The only thing scarier than being faced with new perspectives and questions on my sexuality were the new perspectives and possible answers and what those could mean for the rest of my life. How did I know that I wasn’t straight though? What if being with another man was enjoyable in my head but not enjoyable in practice? Though I was from a small town and didn’t know much about being gay, I also know that I wasn’t giving the topic the kind of serious thought that I needed to until it finally became too hard not to. This wasn’t a conscious thought though – it just never came to my mind as anything urgent or necessary. Not until my body started telling me enough was enough and my heart said “Rob, we need to have a me-to-me.”

The questions surrounding sexuality were nothing but a series of dilemmas that were almost like a “choose your own adventure” book gone wrong. Each choice could prompt several more to choose from and not all of them, if followed, would take you down the necessary path to start a new chapter in your book.

Like most worthwhile things in my life this process was confusing and trying and harder than it needed to be. It’s not my favourite story to tell, but I can own it – it’s part of my life. I wouldn’t be the person I am today without it.

*

One topic that people love to pick my brain about is hookups that stem from meeting online. They don’t look for all the salacious details – usually, anyway – but they’re curious about the concept and the execution. They want to know about the characters involved. The settings. They want to know how all of my stories get formed.

It’s a world that is foreign to a lot of people – like Czechoslovakia. Any friend of mine who isn’t a gay man doesn’t quite understand this domain from the same vantage point as I do. The only thing more surprising than the continued interest of others in this topic, I find, is the fact that I’ve become so comfortable talking about not only the stories, but how they happen. There was a time when both parts to this equation gave me cause for consternation. I was a late bloomer who had a lot of figuring out to do at once – not only did I have to take the first tentative steps towards being a sexual actor but at the same time I had to put some serious thought into the “am I gay?” question. When I finally took the plunge and put myself out there to explore things I was hoping to get some clear direction. Instead, for a while I was spun in several different ones and perhaps more confused than ever before.

I’ve said something to this effect before, but as a single gay man living in 2012 it’s a commonly understood fact that I have met people over the internet and hooked up with them. I don’t go to gay bars, we know this. The parties I go to are generally populated with straight men and when there are gay guys there they tend to be coupled. My life has played out as such that I have only rarely had an organic sexual experience. The rest have all been inorganic – preordained, if you will. We meet after statistics and pictures and brokering what it is we’d like to do together.

At one point in my life, I was really weird about the idea of hooking up online. The reason I started was simple – I couldn’t think of another way to be with anyone.  I did know that in theory I could go to a gay bar and perhaps someone would be like “Sure, why not.” Or maybe I’d meet someone at a party. Or maybe, like in so many bicurious daydreams a guy would take to me first under the auspices of friendship and one day reveal himself to be interested in me sexually and romantically and we’d go from there.

When it hit me that I wanted to take my curiosities further I had to accept the fact that I had some other things to deal with: I was not out (nor ready to be), I was not even 100% certain that I was gay because of my sexual inexperience, and the cherry on top, I was overweight and didn’t feel particularly sexy or datable. The sexual side of life was something I yearned to discover, but was not well-suited to in a manner that I’d call conventional.

As a writer, it’s easy to hide behind words sometimes. There was a certain comfort to hiding behind a dating ad, a website posting or an email from a secondary address. It was one thing to write to a stranger and say that I wanted to be with them; it was much easier than speaking the words aloud.

*

For many years I didn’t consider myself an actor in the world of sex or dating. It was a playground for others but not for me. The notion I had was that I was too fat to date and only people who dated had sex. Therefore, if I wasn’t dating anyone, I wasn’t going to have sex with anyone. Since I wasn’t nearly as attractive as everyone I saw dating, I just didn’t bother thinking about sex much. This doesn’t mean I wasn’t a teenager who jerked off often or had sexual fantasies but it meant that I didn’t have to think about it in real terms. I didn’t have to think about what it would be like to be with a man because I was a scared teenager, I didn’t know anyone who was outwardly gay and besides I felt too fat and too scared to even approach such a notion if it had been handed to me on a platter. I didn’t have to think about what it would like to be with a woman because I wasn’t faced with the prospect of dating and because I figured it was something I would deal with when the time came.

I didn’t talk about sex because there wasn’t much point in talking about it; it didn’t have a high priority in my life or my mind for many years. I was more concerned with making friends and figuring out my life and creative pursuits and entrepreneurial pursuits and having fun. Though I’ve always yearned to be loved, sex was never high on the priority list. It was never a topic that I considered healthy or hilarious or interesting. It was never a part of life that I gave much consideration to. I figured I would eventually but the timeframe was always nebulous; the concept always vague. I assumed it would all work itself out at some point and that would be that.

Sometimes cravings need to be satisfied, even if you’ve never indulged before. I’ve heard people who don’t drink say they could use a drink or those who don’t smoke say they could use a cigarette to steady their nerves. Eventually, that was me and sex – I had questions to answer but nothing to go on. Sex wasn’t really set up to be anything fun at first – it was something I was going to have to deal with to offer some insight into other aspects of my life, despite my reservations. Between the discomfort with my body – in this far-off vision where I had sex I was always thinner – and the embarrassment at admitting my own urges and my own homosexual interests my first steps were not taken lightly.

*

The true first time I was ever with someone is a story I never tell. If you asked me about my first, I always add the qualifier of “the first time I really knew I was gay.” That is my cherished story from Boston. The first time period was not that. I’m only talking about it now, because it’s a piece to the puzzle that is pretty important.

It took place in my hometown when I was there over the 2006 Christmas Break. I can’t pinpoint the exact day when this happened. This was about a year before I really started to question things in January 2008.

I come from a town where it is well known that there are a few spots to go “cruising” – a.k.a., the kind of scenario where you go to an abandoned lot or a parking lot or some such and you have assorted men in assorted cars who are all there for a particular reason and you pray you don’t see a familiar face and you hope that you might find someone who doesn’t totally put you off to hookup with.

I was out with the van on an errand one day. I had been wrestling with some rising rumblings of sexual curiousity and I decided to make a bold decision. I was at the point where it was starting to bother me. I was thinking about my curiosities a lot and I needed to clear my head of some of these questions. I decided not to take the exit to my house after I was done with my errand. For whatever reason, I’d had enough. I needed to gain some perspective and I had no idea how I was going to do it otherwise.

I went to one of these places, a quiet part of town where, for some reason you can pick up AM radio from Boston. As I drove there, I tried not to think too much about what I was doing. I didn’t want to lose my nerve.

I was approached by a guy who was unremarkable to look at. He was the only other person there. He wasn’t particularly handsome per se but he wasn’t hideous. He was in his early forties, though I never asked for a confirmation of age. He was a bit husky and didn’t speak much and I remember being relieved that he didn’t find me to be repugnant. I was also relieved that he seemed normal enough and not unappealing enough that I was willing to go forward. I figured, with my size and heft that I could easily pretend to be threatening if I needed to be and wouldn’t have to fear any sort of unwanted advances.

The guy said that he was straight but liked to experiment. I too made up a few lies about myself because I wanted no proof of what was happening to exist. I said I was from Halifax and I was visiting and that I had heard rumours of this place and then prayed that everything would go smoothly. That I wouldn’t end robbed or something. That he wouldn’t end up wanting to fuck me.

The encounter was hands-off – no talking, no intimacy at all. Just, according to broadly accepted definitions of the term, third base. It was a scary feeling afterwards because I wasn’t overly enthused by it. Being with a man was something that for many years I thought I wanted but I was nonplussed about it. I had hoped for more clarity as to my sexuality following this event, but had no such luck in finding any.

Let’s face it: most guys don’t dislike receiving oral sex. I thought to myself that a girl doing that would probably be fine. If it were a guy I was more attracted to, then that would be fine too. I was not sold on what I’d (actively) done at all. Maybe, I thought, if it was someone that I was more attracted to or had a nice rapport with. It was actually scarier to think that I was more turned off by it than I would have been had I been more turned on by it.

It was over two years before I would hookup again. All of the old concerns still existed and to add to that after all that time and all those fantasies I finally had another dick in the room and it really didn’t do anything for me.

Part two to follow

M is for Magic, M is for Missed Connections (Part One)

I don’t believe much in the idea of magic when it comes to dating and relationships as it is so often presented to us. Thanks to an observant eye and a lot of Mr. Wrongs I’ve realized that magic is what keeps a lot of people from being happy. It simply doesn’t exist in the way it is portrayed in books or movies or music and since a lot of people expect it to happen that way, they end up disappointed. They have high expectations and, when they don’t find them met by a mere mortal, they leave for so-called greener pastures, suspecting their needs can be met elsewhere.

It’s a regular hunt for the elusive Most. As they look more and more, their disappointment grows more and more. Their frustration grows more and more and they miss out on opportunities to be happy. Most is going to light fireworks in your heart so if someone doesn’t do that right away you should just run because they will be of absolutely no use to you. (I hope you sensed the sarcasm in that statement.)

A great example of this is with Derek. He said that he didn’t feel a spark when we went on our date. Here’s the thing though – we had talked for two months prior to this point and knew each other practically inside and out. We knew good things and bad things about each other. We shared secrets we rarely told other people. We said romantic things to each other and we argued. We ran the emotional gamut and were now incredibly familiar with each other. Nevertheless, he was so nervous meeting a guy from online that he said many times he’d have to imbibe a few drinks to feel at ease.

Derek ordered martinis – he wasn’t fucking around.

Going into our date, knowing that this was his plan, I wasn’t expecting fireworks per se. How on earth could I? A statement like that puts a slight damper on romantic daydreams.

Given everything that had happened between us there was a comfortable familiarity hanging over us on the night of our date. (I for one, enjoyed it.) Of course you’re not going to feel the kind of magic you see in romantic comedy films in this type of scenario. We knew each other too well for that. He was sipping a martini to enter an altered state where our meeting wasn’t going to make him nervous. He needed courage to be in a restaurant with me that night – only the liquid variety would do.

Derek neglected the awesome thing – that there was a guy sitting across the table from him, who cared for him warts and all. Who had travelled all the way to a different city, a different province even, to be with him. A guy who was willing to work through things with him. A guy who wanted to take care of him and to love him anyway; to be taken of and to be loved anyway. Someone who couldn’t believe the vision who walked into Second Cup to meet him was his – though that was only for a little while.

That’s as close to magic as it gets really, though most people are foolish and overlook it for dreams and showiness that are better suited to a young child’s fairy stories. We mask this pursuit of a perfection that doesn’t exist with terms like “love at first sight” or “magic” or “spark” and everyone knows precisely what we’re sacrificing when we complain that yet again we didn’t find any of it.

*

That said, I feel that impossible, silly sort of magic still exists in the form of Craigslist Missed Connections.

I have an absurd fondness for Missed Connections and I also have a really great track record with them. I’ve posted a bunch, but I’ve actually had three responded to by the person I was seeking to connect with. Three messages in bottles that I tossed out into the world came back to me. Sometimes I tell myself that it’s not the most unlikely thing ever because gay people love Missed Connections – I for one check them daily – but nevertheless it’s a big world and people, as we well know, don’t even like to respond to those they know and ostensibly care for in some manner. (People with names rhyming with Eric, for instance.) I guess that makes it all the more special when a stranger contacts you out of the blue.

When two people connect over something like this – at all – I think chalking it up to chance, or kismet or something in that vein is not being generous enough. As much as you can rationalize it intellectually, most odds are in favour against a Missed Connection ever coming to be.

Here are the abridged stories of the three times I heard back from my quarry.

1. The shop boy from Restoration Hardware, Providence, Rhode Island

I was in Providence for the day for work. I was interning with a company that allowed me to take some initiatives and noting that the target market for their services – a particular coffee chain – had eight locations in Providence and zero users I had an idea. I would visit each location personally and let them know about what our company offered. I finished after two hours, due in large part to making a logical map of which stores I’d hit in what order, but also because Providence is a bit of a ghost town on a hot Saturday afternoon – I didn’t really have to contend with any line-ups or traffic.

I spent the rest of my time exploring the city, taking photos of the architecture, exploring Brown and RISD and genuinely enjoying one of the best days of my life. I capped it off by going shopping at Providence Place mall and, for one of the first times I can remember, found myself in a flirty conversation with a random storekeeper.

Despite the amount of people in the mall and out for the water fires, it was really quiet in Restoration Hardware. Because of this and the fact that we got on nicely the shop boy was able to spend a lot of time with me. He was the only staff member on the floor and offered me his full attention. Our half-hour conversation went beyond decorative home items – we talked about our lives and our interests as if we were trying to build something. We both intimated that we were gay but never said so outright. He told me I should check out the water fires after work and part of me wanted to ask him to join me but I was too nervous about ruining the moment, so I didn’t.

I posted a Missed Connection when I got home and about two weeks later I opened my email box to see a strange email address. The subject line, curiously, was “Well ya see” and the body of the email read as follows:

“People actually do check the missed connections things.
Surprise!

[Redacted]
Restoration Hardware”

Stunned cannot accurately describe how I felt.

It didn’t turn into anything, mind you. I emailed him back, but never heard from him again. I did, and still do, take comfort in the fact that he was so obviously flattered and remembered his time with me, if only for a short while.

2. The verbose tour guide from the Harvard Quad, Cambridge, Massachusetts

Some Harvard students work for a tour company during the summer and offer a fabulous way to see the university. They conduct an elaborate, fact-filled tour of the school for tourists on sunny Cantabrigian summer afternoons. I went on one (with a Torontonian tourist I met online, no less) and we had a really great time.

But I digress.

I was crossing the quad one day, destined for my class at Sever Hall and I passed by one of these tour groups. The guy giving the tour caught me off guard with his word choice. He was using some amazing vocabulary and had a really nice voice. As I turned, I noticed that he was also quite cute. Though my gaydar isn’t always the strongest, there was no doubt in my mind that he was light in the loafers. If it wasn’t the timbre of his voice, it was the small grey backpack. If there is one quality that I find elusive in a man, it is intellect. It’s a rare occasion that I pass up the opportunity to find out more when an intelligent guy enters my sights and so I wrote him a Missed Connection. I asked him to describe himself when he wrote me back. We didn’t really get the chance to make a connection per se, but I wanted to change that.

He wrote back swiftly. As he described himself, it was clear that it was indeed the guy I saw. He mentioned the backpack, a detail I had not included in my description. I wrote back to confirm that it was him I was talking about, but by then his curiousity was no more. I kept my eyes peeled when I’d walk across campus, just in case I should happen upon him giving tours again, though, as if he had been a mirage, he never reappeared.

3. The adorable fundraiser from the streets of Chicago, Illinois

One day in Chicago, me and one of my bunkmates from the hostel decided to explore the city together. It was my last full day in Chicago and I wanted to make the most of it. He wasn’t sure what to do but I had an idea – I wanted to see Wrigley Field. I am not at all a baseball fan, but I felt compelled to visit it nevertheless having seen so many other Chicago landmarks. We ended up walking from there through Wrigleyville and Boystown – Chicago’s gay district. It was funny because I, being an idiot, just thought Chicago was really excited for the gay pride weekend. It didn’t occur to me that we were in Boystown until well into the afternoon. Though generally, I’m kind of terrified of gay districts, it was a pleasant experience, much like the rest of our afternoon – the highlight of which was a meaningful life discussion, gazing at sailboats and a surreptitious $2.49 six pack on the edge of Lake Michigan.

There were all kinds of people collecting money on the streets in Chicago – it seemed like every cause under the sun had their hand out. I noticed the Human Rights Campaign collecting and took pause. Though I would like to say it was solely because of the organization, it was also because one of their fundraisers caught my eye.

Benevolent soul that I am, I convinced my friend that we should stop and hear this pair out.

Part two to follow

Theory: Saying Goodbye Isn’t Always Pretty. (The Fling Edition – Part Two)

The Fling and I didn’t see each other again until Monday, which gave me some time to evaluate how I should proceed. I decided that I was going to give him a mulligan on his Friday admission because he’d been drinking, for once in my life avoiding the adage in vino veritas. Certainly The Fling couldn’t be thinking that way. Unless he said something else to that effect I was allowed to keep on enjoying things as they were.

That night we were in my bed and he mentioned how he only wanted to talk and how he wanted to get to know each other – he wanted to slow things down – and I had the worst feeling in the pit of my stomach. I wanted to pretend that this wasn’t going to happen. I wasn’t interested in dating him.

I was just beginning to feel my oats as a single, thinner version of myself living in the big city and without the weight of my family life or my small town on my shoulders I felt less rush to fall into someone’s arms. I’d been with Patrick only a few days before and he was still a possibility at the time. My conversations with Derek were ongoing at the time and we were taking about meeting and would a few weeks later. I knew I had a much stronger connection with the both of them and found myself a lot more interested in the idea of dating one of them. They were better fits – more book smart, more educated, more subdued, more sophisticated, more relaxed. They were both better yins to my yang. The Fling was very sweet and obviously cared about me and I treated him as nicely as I could, but I just didn’t feel what he so clearly felt.

I had no intention on dicking him around. I wasn’t going to do to him, what so many men had done to me – that is to say, there would be no ambiguity about my thoughts on dating.

We had the conversation at two AM in my bed. I didn’t have the nerve to wait until morning. He was ready to walk out at first but I told him he couldn’t. I reminded him how hurt he’d been when I disappeared and I told him that it wouldn’t be fair of him to do the same thing and not to hear me out. We talked for hours – about everything. The more I talked to him on a deep level I learned that he was different than I anticipated. He’d lost his mom a few years back and this had caused him to grow up quite a bit. He’d dated and fooled around and had been in relationships. I’d certainly misjudged his maturity by focusing on superficial suggestions that it was a trait he lacked. It still didn’t mean we could date, only that a lesson had been learned for the future.

I thanked him for everything. The first hickey. The listening. The making me feel special. For putting up with me for an afternoon running errands in Westmount and carrying my bags. For being my first liaison that had ever lingered so long and felt a little more real than all the rest. For ushering me further into manhood. For making it so that I could no longer say that I’d never had a torrid little love affair. For giving me a taste of what it’s like – for better and for worse – to be together with someone.

Eventually “fuck you” turned into him still wanting to be friends.

Eventually him still wanting to be friends turned into him deleting me from Facebook and disappearing for almost a week.

Eventually him deleting me from Facebook and disappearing for almost a week turned into a calm reappearance in my life and eventually we got together as friends.

*

While it was evident that we liked each other’s company and clear we couldn’t keep our hands off each other, there was the looming feeling that our continuing to spend time together wasn’t right for either of us.

The Fling knew there was no possibility of dating me. I knew that I’d told him how I felt and I promised myself not to renege on my word. We were just craving a connection, I told myself, we were just two lonely guys with a little history, who knew there were comforting arms in each other. The last time he ever came over I remember wanting to just lie with him and for things to be quiet and calm. He couldn’t stop talking and he turned off Death Cab and he turned off The Sea and Cake and bugged me until he could pick the music.

I wanna fuck you like an animal.

I wanna feel you from the inside.

I told him this was a bit on the nose and as he vigourously made out with me, I just kind of sat there, wondering why we were even bothering.

*

The last time we went anywhere together was out for drinks. I was having a miserable Friday – I’d lost a retail job and I hadn’t heard from Derek since we texted that Wednesday. I was a few hours away from officially cutting Derek out of my life. Soon I would send him furious text messages after noting that he’d deleted me from Skype – the one thing that we used to communicate.

Patrick had told me that he wasn’t going to be contacting me again about two weeks prior. I still had the fling though, steadfast as ever. He was very willing to join me for drinks and we had a comfortable time together. As we drank, hands wandered and lips met and we mused aloud about how this wasn’t a good idea but pressed on anyway. It was nothing about the fear someone might notice; it was everything about knowing in our hearts that it wasn’t exactly our best call. A waitress asked us if we were “queer;” I almost said “No, just really bicurious.” She talked about how she was a lesbian herself. She loved getting “queer customers” at the bar (a rare occurrence at the Irish pub we were at) and gave us our next round for half price.

The Fling disappeared abruptly as the end of our night neared. I was debating whether or not I should ask him over. I wanted the company, but I didn’t want all the noise. He sent me a text saying that he was good for nights like this, but not much else. He needed to be alone. He’d left when he said he was going to the washroom.

It was too late to catch the metro home, so I walked all the way over to St. Denis to get a night bus. I was drunk and couldn’t stop thinking about how the embarrassment of riches I once had was over. I knew that Derek was gone at this point. Nevertheless, it was walking by Patrick’s street as I tried to find a stop for the night bus that almost had me break down into tears. I’d almost had my pick of three, now I had absolutely nothing.

When I got home and discovered what Derek had done I called The Fling. It was after three, but we talked for over an hour. The Fling mentioned that I was one of his best friends – and it was a great comfort that I wasn’t alone that night. I didn’t invite him over, but, as we talked, he was there with me nonetheless. That sentiment wouldn’t last much longer.

*

Following this night, The Fling became rather cold and abrupt with me and I had no clue what caused this change. He told me that he had a guy in his bed, information I didn’t feel I needed to know. He was no longer an interesting Facebook chat partner. Our increasingly rare texts to each other had grown terse. Nothing prepared me though for our final meeting.

The last time I saw The Fling I was meeting a few friends for drinks and had to get off the metro at the stop where he worked. I’d had a few beverages beforehand and in a peculiar act of timing, I ran into him outside of the store where he had just finished work for the night.

I was happy to see him, but the feeling wasn’t mutual. He couldn’t have tried harder to make things awkward between us during our brief encounter. At one point he was playing with the string on his coat and said that this is the sort of thing he did when he was angry and needed to distract himself. In the end I just walked away from him, largely ignored and feeling kind of upset. Baffled mostly. I sent him a text asking what I did wrong. It was part curiosity and part entirely in earnest, though I should admit, it was part baiting because if he was going to play head games, I was going to say, “Fine, you’re skins.”

During the walk to the bar I realized that this was it for us. I needed to take the out I was given, because it was there and this was probably the one chance I would ever get to leave and not hurt him. He was mad at me for whatever reason and that was fine. As long as he wasn’t heartbroken, I was willing to accept a lifetime of him cursing my memory.

When I suggested that we hang out on the Monday afternoon, I suggested we meet at Starbucks in Westmount and then go run some errands. I needed a bottle of red wine, a modem and I wanted to go to the Winners at Alexis Nihon. To me, it sounded like a lovely afternoon to meander and spend time with one another.

I deleted his phone number from my address book as I walked to the bar.

He thought that idea sounded awful. His suggestion was to take a bus out to Dorval and to go explore an abandoned Warehouse about a million miles away from my desires to spend the afternoon in Westmount.

I deleted most of his texts as well.

When I got to the bar he called me. I knew it was him only because of the timing and because I was pretty sure I recognized the number.

I picked up. I considered asking “who is this?”

“Hey you, what’s up?” was the response to my simple hello. It was The Fling. He sounded cheerful.

“What’s up?” I asked incredulously, stunned that he would have the nerve to call, whitewashing over what had happened fewer than fifteen minutes before.

“Yeah,” he said, still cheerful.

“You’re serious?” I asked.

“Yeah,” he said, “What are you up to?”

I couldn’t believe that he was doing this to me. I knew that he was only calling because he liked alcohol. And fun things to do. And because he could easily meet up with my friends and I. Maybe we’d make out a little and do stupid things. It was as if he hadn’t been hateful to me at all just a few minutes before. It was as shocking as when he talked about dating on a Friday when he’d cursed my name on Tuesday.

“FUCK. YOU.” I said, and I hung up. I went back to drink with my friends.

*

I think it was wise to take the out I was given because I knew that we shouldn’t be seeing each other anymore. The more we did, the worse we were off. It was hard not to see each other. When you have a guaranteed option not to be lonely now, even though it might not be such a great decision long term, it can be easy to throw yourself off course.

I can’t say that I’m proud, but like the way it ended with Sebastian it was final. And it was real. It was just as uncomfortable and unexpected as life itself.

I didn’t mean to say fuck you, I meant to express my feelings more like so:

“I’m tired of you being hot and cold with me. We both know that we’re not a good match to date each other, but that doesn’t mean we can’t be friends and be nice to each other. If you’re going to be mean-spirited towards me one minute, and act like I’m your pal the next, then we can’t be anything. I don’t deserve that kind of treatment from someone. If it’s due to any lingering hurt from having to quash any ideas of romance with me, you have to understand that it needed to be done. I’ve had people play with my affections before and it really hurt. I was just trying to spare you that much. I wasn’t perfect with you, but at least if I can be honest with you about that, I can rest easy. If you cared about me at all, even as a friend, you never would have pulled that stunt outside work. Let’s just move on and hope that things work out well for both of us.”

That’s what I was trying to say with fuck you, believe it or not – at least something to that effect. I doubt he picked up on those steeped meanings. He probably thought I was angry instead of frustrated, he probably thought that I hated him – I was just confused and hurt. Regardless, what followed was exactly the kind of relationship we needed with one another. None at all.

*

The Fling did some detective work to find me after I went to his register – and I know he could again if he wanted to. Though I do look back on my time with him fondly, sometimes to a dangerous point where I want to get back in touch, despite myself, it is a continued relief that we pursue our lives separately from each other. There’s a certain comfort in the fact that we’re now strangers to each other.

I never got to date when I was young and thought I missed the boat on doing so. I suppose for a few weeks last year I got my chance to get a do-over. I was able to just enjoy the moment with someone and to not take dating super-seriously for once – to be young and stupid and infatuated.

He was eighteen and I was twenty-five. That’s why, even though I rage against maturity sometimes, I couldn’t help but notice, when we were in my bed the night we “broke up” that the rationales coming out of my mouth were incredibly adult. I told him that it would all make sense eventually. I hope it will all click for him one day.

He’s left an indelible mark on my memory and one of these days I hope he finds exactly what he’s looking for. If I could say one more thing to him, it would be all of this and one thing more:

Stay strong – boys who want to explore abandoned warehouses won’t elude you forever.

Theory: Saying Goodbye Isn’t Always Pretty. (The Fling Edition – Part One)

In case you’re reading this – Know that I don’t hate you. Consider this a love letter to the weird and wonderful time we enjoyed with each other. -Rob

The Fling*

The Fling came at a time in my life where I had an embarrassment of riches when it came to male attention. A few short weeks later it would pass and I would find myself with none.

The Fling messaged me on the same dating site as Sebastian did, though a few days later. The fling was eighteen – a cegep student and a cashier. He was certainly cute, but he was also young. Our age difference was seven years. To say that this alone gave me pause, is not entirely true. What gave me pause was the fact that he acted like an eighteen year old. When we’d chat he used a lot of capital letters and slang I didn’t quite understand. He wanted me to bring him a bottle of Sour Puss from Nova Scotia because we had a flavour that Quebec didn’t. Sex came into our conversations a lot. This is perhaps what made the next part so difficult – despite knowing that upon my imminent return to Montreal I would have a cute, friendly, willing guy awaiting my arrival with bated breath, I had trouble with one huge aspect.

I was at a point where I wanted a relationship. He was not.

You’re probably a little confused, so allow me to explain. Before I returned to Montreal I was in a really lonely spot and wanted a relationship more than anything. I think this was in part due to my exile of sorts in Nova Scotia. There was no dating, only slightly more intimate liaisons and a social life that wasn’t terribly rich. It’s only natural that I was craving companionship and stability. My family unit was crumbling and I felt, at times, like the only person in that house, in that town – hell, on that island.

After I returned to Montreal, I saw the world differently to say the least. I was a new man with a fresh start and I yearned to enjoy it. The flirtations. The free coffees. The new clothes. The new possibilities. The eligible bachelors.

The Fling was pretty indifferent to the idea of a relationship. Once I knew this, our efforts in getting to know each other seemed like a waste of time. I had a few misgivings based on our conversations but this made me realize what I had to do. On Thanksgiving weekend I abruptly stopped our conversation – I told him there was no point because I wanted something more serious than he did. I got rid of him from Facebook and put him out of mind. I moved to Montreal a few weeks later and overwhelmed by all the beauty I saw around me on the metro, at the coffee shop and traipsing through the Plateau I will admit that my mind didn’t often drift to him, if at all.

*

All I knew of The Fling’s work was that it was for a particular chain store. I didn’t think of this when I visited a popular shopping centre that was on my route and noticed him at the cash. It never occurred to me that I would find him there. I made sure to go to a different register and to keep out of his sight. I looked like shit that day. I decided that I’d come back another day to say hi when I looked better.

I would like to admit that it was merely regret that caused me to later go to his register – some desire to make nice. It was actually three things. My belief on fate and that I was meant to meet him, the fact that I was now like him, willing to forgo dating and finally the fact that he was really cute in person. It seemed harmless to at least say hello.

*

It took a few attempts to finally run into him while working. When I finally had the chance to go to his cash, I looked much more presentable than I did that first day. I was buying salad and jambon d’autrefois. He immediately recognized me and screwed up the transaction of the client ahead of me. When he finally got to me he said “Hi Rob.” He didn’t even try to pretend he didn’t know who I was.

Surely due to this, he was ice cold and didn’t charge me for a bag, sarcastically saying that friends didn’t charge friends for bags. I didn’t realize that he was sarcastic until he told me this later, the whole exchange was so quick and so surreal that I wasn’t really sure what to make of it.

The next afternoon I discovered an email in my inbox from The Fling. It had been sent in the middle of the night. He said that seeing me was rather unexpected and that he wanted to discuss a few things. I emailed him my number and said to text me as I didn’t have internet at the time. He texted me not long after and we decided to make plans for that night.

When he texted me later to figure out our exact plans I was out for a drink with a friend of mine. The Fling wanted to do something cheap which ruled out a bar or food. I didn’t want to do coffee. I suggested I bring a bottle of wine over to his place so we could talk. He liked that idea. I was to meet him at Parc metro.

We greeted each other warmly as if we were old friends. It was as if there had been no unpleasantness.

His apartment was a disaster – he had just moved in and there boxes and items once in boxes scattered everywhere. The flirtations crept in slowly as we sat in chairs across from one another enjoying a cheap vintage from the SAQ Express. Both of us tried to avoid their existence. I think we made it through twenty minutes before we started making out and the discussion he wanted to have never quite came to pass. We revisited old discussions instead – ones in his single bed – and I didn’t leave until eight the next morning.

*

I got several texts during that day from The Fling and that night he wanted to take me out for drinks to make up for the fact that I had purchased a bottle of wine the night before. He kept talking about how much money I spent on the wine and how wonderful it was. I kept sipping my beer and hoping my facial expression wasn’t giving away the truth. We drank a gigantic pitcher of beer together and finally after him mentioning it one too many times, or me having had one too many beers, I vouchsafed that the wine had only cost eight dollars.

After rounding up some snacks, the two of us headed back to my place and he stayed the night again. The next morning we dined at an Asian noodle place around the corner from me. I was really enjoying the chance to not think so much and to just enjoy a guy’s company. I felt like I was finally getting a taste of what it seemed everyone else had. I felt young and foolish and, for once, like I was going with the flow when it came to a guy. I didn’t ask many questions – I was simply enjoying the here and now.

The next night, Friday, he went out and sent me drunk texts and I invited him over because his apartment was so much farther from downtown. I took care of him, giving him hummus and water and lending him my red sweatpants. He started talking about how wonderful his life was and how awesome it was to be dating a twenty-five year old guy with his own apartment. I remember being terrified. He’d hated me Tuesday and now we were dating?

I knew this was the beginning of the end, even if it might have simply been the Jameson talking.

Part two to follow

*Obviously a pseudonym