The per­ils and mis­ad­ven­tures of online dat­ing.

I get an OKCupid message from someone who is in town visiting family for a few weeks. Even though I know nothing can really happen long-term, I agree to meet him for a coffee. He’s from New York, he’s a photographer-slash-musician, how bad could it be? Even though he’s not the most handsome guy, he’s funny and getting cuter as the date progresses. We decide to go for another drink and end up seeing a movie. We sit in the back row and somewhere after the credits but before the bottom of the popcorn we start making out like teenagers. A middle-aged woman sitting alone two seats away shoots daggers at us.

I know lady, I’ve been there, we’ve all been there. You’re alone and there’s some gouge-your-eyes-out couple making googley eyes at each other and you just want to vomit directly in their faces. As much as I’m sympathetic, I feel the need to seize this spit swapping opportunity.

After the movie, he takes my hand while he walks me home. He seems very comfortable with me for how long we’ve known each other (a whole three hours), but I have to assume it’s because he’s a limited-time offer, right? If we were in NYC he’d probably stress about this small gesture of hand holding instead of flaunting me around the block like he won me at a carnival.

That weekend, he comes over to my place for dinner, but since I’m in a no-cooking phase I suggest BBQ takeout. It’s hard to take dainty bites of something as sloppy as a pulled pork sandwich, but what do I care? This guy will be gone in a week and I have a craving. I devour my sammie in a grotesque five minutes, hardly coming up for air. Somehow I’ve got BBQ sauce on my neck and I’m starting to get the meat sweats. I’m a charmer.

He mentions after we finish our sandwiches that maybe eating them was a mistake because he’s gluten-intolerant. I don’t usually buy the whole “gluten intolerance” thing and I ignore his comment. He holds his shit together (pun intended) and we continue drinking wine and chatting.

He notices my guitar and asks if he can sing me a song. My eyes widen, frightened of what I’m about to hear. He probably has a specific song queued up for this very occasion. God help me if it’s awful, because I know it will show on my face. He begins playing and it’s actually a bit of a downer tune. I’m glad it’s not some schmaltzy love ballad and I’m reluctantly impressed. A sad song is more manipulative though. This guy must get a lot of sympathy action.

After a little making out he insists that I play him a song. I go with the ukulele instead of the guitar and play the only song I know, one I learned at the request of another online dating prospect. Maybe that song will finally do what it was supposed to and get me laid, after which it will become my secret serenading weapon. My performance secures another half hour of making out before we leave for a friend’s party, where we get drunk and handsy before stumbling back to my place.

We proceed to have clumsy sex.

This guy is all over the place in bed. He seems to be speeding through a set routine where only at the end will he get to do what he wants. He’s moving from one part of my body to the next so fast I have to tell him that we’re not under any time restrictions.

He loses his boner. Boners are so fucking sensitive. I’m left unsatisfied. But I can’t say he didn’t try, he was just so…sloppy. And yes, we were drinking, but something about his sweaty, lumbering body really repulsed me. It just wasn’t going
to happen.

We fall asleep, but throughout the night I repeatedly wake up to him apologizing for getting up to go to the washroom.

Finally I get up to use the bathroom myself and as I put my feet on the floor I feel something squishy. It’s the condom. For the record, my trashcan is literally a foot away. As I enter the bathroom I see a balled-up bath towel, sopping wet on the floor, and the remnants of what appears to be an overflowing toilet. Perhaps I was too hasty in disregarding his gluten intolerance. But if you’re on a date, how about not eating something that makes you shit your pants uncontrollably? Or maybe he clogged it from hurling? I’m left to choose from the buffet of gross things that could have happened here. Puzzled still, I go back to bed, teetering on the edge of the mattress so as to not touch him.

I wake up relieved that he isn’t beside me. Did he leave? Am I free to disinfect the bathroom and burn my sheets now? Nope. He’s in my kitchen, helping himself to some coffee after drawing the world’s largest cock on my chalkboard. I laugh at the irony of this massive dick with the memory of his less than stellar performance fresh in my mind. I get into sweatpants and make no effort in my appearance as we sip our coffee in awkward silence.

The next two days he keeps texting me and I reply with short go-nowhere answers while deliberating how to get out of this mess. How am I supposed to explain my hot and cold demeanor when I don’t understand it myself? Sure he was gross, but we’re all gross sometimes. And even though this is what I say in my recurring don’t-be-an-asshole-have-some-sympathy pep talk to myself, I’m still disgusted by the thought of him. And finally I do something that feels completely out of character for me: I lie. I say I don’t want to see him again because he’s leaving soon. He sees through this and pressures me further. I dig myself deeper saying I shouldn’t have slept with him so quickly and I’m not that kind of girl.

At the time I thought this was a lie as well, a way to wriggle out of any real confrontation, but the more I think about it the more I realize it’s all kind of true: the person I am so disgusted by isn’t him at all, it’s me. I thought I wanted a relationship, but I keep setting myself up to fail dating people who are unavailable: geographically, emotionally, gastronomically…

I feel terrible. But then I realize that all the things I was doing to repel him, like not caring about what I ate in front of him and what I looked like, not reaching out to him and keeping my texting brief, were the exact things that kept him interested. I was elusive. Independent. Confident. I was behaving like a guy would, a guy I would be frustrated with and probably attracted to. This is a learning moment cocooned in an awful experience. All of the sudden I feel empowered. This could define all future relationships where I treat men poorly only to leave them wanting more!

Or, I could just find someone nice, who lives in this city and who can handle his pulled pork.

The per­ils and mis­ad­ven­tures of online dat­ing in No Fun City, with bonus date-stalking tips from a tech-savvy sin­gle lady.

I am officially in party mode. I eat toast for dinner off the lids of Tupperware because all of my dishes are dirty. I’m trying to shoehorn as much fun into my life as possible. There is no time for such banalities as cleaning. I’m gross. This, I’m sure, is the residual effect of being in a relationship for most of my twenties. This last year (last gasp) is my chance to party, and I’m taking it seriously.

I have tickets to see a band I like that no one else seems to know so I’ve decided to go alone. As I ready myself to head out I get a message online from a guy in town from LA. He’s bored. I ask him to accompany me to the show, which starts in half an hour. He responds immediately and just like that I have a date.

I wait for him outside the venue and as he gets out of the cab I wince a little cause he’s in a suit. He’s tall, and the suit…is not. But it is wide–as is his tie. Is this how people dress in LA? He’s perfectly polite and apologizes profusely for being five minutes late and quickly buys me a drink. We chat a bit about the band and watch the show, which ends early. I’m feeling restless and not ready to end the night when a friend/coworker texts me that there is a party in Railtown and do I want to go with her and her hubby? Elated that I actually have a date (albeit a poorly dressed one) I accept.

I introduce him to my friends and, probably due to the few drinks we’ve already had, he starts explaining how he’s writing a graphic novel. He pulls up a terrible Deviant Art-y rendering on his phone and explains how it’s kind of like Tomb Raider. I gesture to my friend silently that this guy is the biggest nerd by pushing up my imaginary glasses. I’m an asshole.

I continue drinking.

My girlfriend and I proceed to drink so much that later, when her husband runs into the guy who threw the party he’s confronted with,”Oh yeah, you were with those drunk girls.”

I am those drunk girls.

That was me almost falling up the stairs then trying to recover by making it look like some quirky lunge. That was me yelling, “I know yoooooooou!” to someone I recognized from a magazine. That was also me attempting a pull-up off the ceiling pipes. And that was definitely me making out in a stranger’s loft just to feel the pressure of someone else’s face against mine.

I don’t remember how I got home.

I wake up confused. I feel tangled up and it’s hard to move my arms. I then realize I’m half out of my bra and shirt with an arm out of each. I have no pants or underwear on. I step onto the floor narrowly missing a gelatinous substance–is that vomit? It’s white. I touch it. It jiggles. Did the cat do this? I don’t usually hurl when I drink, this couldn’t have been me? Could it? Can a human make this…texture? I continue to the living room to where the contents of my purse make a trail from the front door to my bedroom. I’m 95% sure I didn’t get violated but I did lose my bus pass and it’s the beginning of the month. I have reached a new low.

I call my girlfriend and describe what’s on the floor.

“Oh that, that’s just bile.” Oh, no big deal. This is not something I’m accustomed to finding on my floor! Her flippant attitude further illustrates how many experiences I must have missed by being in a boring couple for the last eight years. Still, I could stand to have missed the bile.

I get a message from LA guy and he says he had a great time (I bet) and that my friends are so nice and wants to see me again. I say I’m busy and don’t mention that I hope to never see him again, ever. He’s a perfectly nice guy, an actual gentleman. But kinda milquetoast. This is precisely why the idiom “nice guys finish last” exists. He’s just not exciting in any way. Also he doesn’t live here, so he could never really be a contender. This is how I justify blowing him off.

The day after is a workday and I wake up with a residual shame-over followed by the relief of knowing I didn’t do anything crazy the night before. It’s like my body remembered the previous morning’s guilt, “Shouldn’t we be checking our phone for errant drunk texts by now?” No. Thank God.

At work I walk past my girlfriend’s desk and she’s on Adrianne Curry’s Twitter page. I ask what she could possibly be doing there and she says, “Don’t you remember? Your date said he was seeing someone who was on Top Model, then, later in the evening he said his ex had over 300,000 followers. I’m piecing it together, this must be her!” I love her for doing this. This makes me judge him even more because Adrianne Curry seems like a dummy. Suddenly any wavering thoughts about blowing him off dissipate. I could never date anyone with such questionable taste.

He writes me a few weeks later when he’s back in town for work. I politely decline to see him again and he sends me the most decent response saying, “You deserve someone really great. I hope you find that person.”

Suddenly I feel guilty. I treated this guy like a rental car. I needed someone to take me to the show and he was right there. It hadn’t occurred to me that I could try to parlay this into something more or that he would even want that. Maybe I subconsciously prohibited myself from liking him to avoid the hassles of a long-distance relationship.

Or maybe he’s just not my type.

Meeting men organically—in person first—is better than online. I will admit that. But I will also admit that for every date I have with a “real life” person, I have around five dates with people I met online first. Just because I’m trying to hedge my bets doesn’t mean I wouldn’t rather an effortless meet-cute.

It’s a couple of months ago, and a friend of mine’s band is playing a show. Our group of friends gathers for the occasion. We meet for pre-drinks at my place, and are pleasantly soused when we get to the venue. We’re dancing and being goofy when my friend notices someone he knows and introduces us. This guy is cute but I’m just trying to have a fun night with my friends (and I’m already too drunk to seem adorable) so I hardly talk to him. The next day in the murky haze of a hangover it dawns on me that this guy may have been a real fox. But I can’t be sure so I do what anyone would in this situation and I Facebook stalk him.

Suspicion confirmed. He is hot. But I can’t tell if he has a girlfriend. Because I hardly talked to him and I don’t think it makes me look crazy I send him a friend request. Meanwhile, I frantically text my girl friend to ask if he’s single. Silence. I finally get a response, days later, just as he confirms my friend request. He’s single (!) and I can only explain what happens next as a pure and simple manifestation on my part.

I run into him way out of the city at a Starbucks.

I am flustered but I MUST approach him. So I walk up and say, “I think I know you.” We have a little nothing-chat then I get the hell out of there like it’s the scene of a crime. The longer I talk to him the better chance I have of saying something stupid so aborting and trying to pass it off as being cool seems like the best course of action. I freak out when I get into work. “You won’t believe what just happened!” The entire staff of my workplace is married and they live vicariously through my dating horror stories: to them, my love life is a source of amusement.

I get a message from him shortly after the Starbucks incident. “How weird was that?!” Excellent. I can’t help but feel I’m making this all happen. I am the writer of my own destiny!

I stalk him further by perusing his “likes” before deciding to post something about one of those things passive aggressively. Trap set. He almost immediately comments on it in a private message. He asks if I’m going to a show of a band we both like. I say I’m not but invite him for a drink the next day. He accepts. Win.

He arrives for drinks…in a tank top. AND a bandana. Hmm, really? Is this supposed to say “I’m not trying too hard” or is he really not trying hard? He’s very sure of himself, bordering on conceited. We all know that’s attractive, even if we don’t want to admit it. Or maybe this is just my own dysfunctional taste.

Halfway through the date he starts to explain how he was in a serious relationship, which broke up about a year ago, and since then he’s just “been having fun” but “people do fall in love.” I say to myself that this is a mixed message, but is it really? That’s what I want to believe but deep down I know he just wants to “have fun.” I don’t care. He’s cute, I like him, and everything is good on paper too (he has a job, seems stable, and he was in a relationship so I know he’s capable of commitment). He walks me (almost) to my bus stop—which is kinda lame actually, how hard is it to walk the extra 20 feet? But we kiss, and there is something there that is undeniable. Lust.

He goes away on vacation. I send him an invite to this party happening right when he gets back. I only half expect a response but surprisingly get a message from him the next day. He says he’s not sure he can make it because he’ll just be returning but he’ll try. I hold out no hope. I don’t want to get excited for nothing.

The night of the party I get a text from him at 12:30am. “How’s the party going?” “Good, you should come by”…”Well it’s going to take me an hour to get there, should I still come”…”If you want to see me.” He shows up right as the last two people are leaving around 2am. I guess he’s staying over?

I have bruises all over my ass and thighs from his hands the next day. I don’t care. We take a shower (together), go to breakfast, and do it all over again. Two days pass and we meet again at my place. We’re supposed to watch a movie. We have sex. I’m a little worried I’m entering into fuck buddy territory but it’s fun and maybe I can do that. The last time I did that was nine years ago and it ended badly with me in a puddle of my own tears but I’m older now, wiser, I can handle it….maybe.

We meet again, sex again. And I just have to ask because I’m starting to feel gross: “Are you sleeping with other people?” He says yes and I reply, “I don’t really know how I feel about that.” But, then I immediately realize that’s bullshit and I say “I’m not okay with that.” He says he doesn’t want a relationship and then there’s nothing more to say.

I could have argued and been really needy about it, but what’s the point? I shouldn’t have to CONVINCE someone to want to be with only me. He is lucky to even have the chance. (Girl power!)

Don’t get me wrong, I’m all for the free trial. You need to see if you’re compatible in the bedroom, of course. But that free trial expires at some point and you need to make the call. I feel like he’d already had enough of the cookie to know. (Though there’s always that part of you that thinks: maybe I should have ridden it out longer. Pun intended, of course).

We have sex again but I can’t come. We get dressed and he pulls me in for a kiss by the fly of my pants, which was actually really hot but I can’t share a dick. I can’t. I won’t. I go cold. He drops me off and says, “call me” and all I can respond with is “why?” I get out of the car. I feel proud of myself for having some self-respect.

By cutting this “relationship” off I’m protecting myself. I don’t want to develop real feelings for someone who doesn’t want me that way. But I can’t stop thinking about the sex. It’s all consuming. I don’t even think I miss him as a person at all but the sexual desire is tricking me. This feels like a big deal, helped along by the very weird fact that I keep running into him. Life is cruel like that. We act like friends when we run into each other but it’s still unnerving to be so cavalier with someone who has had their face in your vag.

The weekend arrives and I get a little tipsy on another bad blind date. I don’t have anyone to stop me so I drunk text him. I am trying to booty text him. But how does that work? I just start with “hey there.” I imagine if it’s on then he’ll respond with something like “is this what I think it is?” and then I could say “maybe” and then we’d be doing it on my kitchen table in no time. But, alas, this is not what happens.

At any other time of day the conversation we have would be innocuous because it’s essentially the kind of chitchat that happens between strangers. “How are you doing?” “How’s your job?”…etc. Except it’s 1am. No one makes mention of the time and it ends as abruptly as it starts with me not answering his last text, which didn’t need answering anyway. He didn’t try to keep it going. Was he just answering to be polite? I try to forget it.

A few weeks go by and I run into him again. I’m with a friend. And as soon as we’re out of earshot she says “holy sexual tension!”  He couldn’t keep his hands off me, touching my necklace and stroking my arm. She said I was super cool about it (because I needed to redeem myself after the drunk texting incident). Are we just going to keep going back and forth playing it cool? I guess I just assumed that he would realize he DOES want a relationship and come crawling back. But if I analyze things rationally, he doesn’t know me well enough for that to happen. There isn’t enough “us” there to run back to.

He starts following me on Instagram.

My social life suddenly looks a lot more interesting. Look at me at a concert! Look at me out with friends! Look at me with this random hot guy (who’s really just my friend’s boyfriend on loan)! Am I behaving like a maniac? Or is this just what people do now because we are so crippled by our fear of rejection that we can only communicate with wildly staged photos and vague status updates. I don’t follow him back but that doesn’t mean I don’t periodically check on his feed.

One day after a three second tug of war with myself I check to see what’s new for him and there it is. Dinner for two tagged with a cute girl. The next photo is breakfast for two with the same girl tagged in a comment “you are so lucky.” My heart sinks. I immediately feel awful. How could I be so stupid? I thought he didn’t want a relationship! Surely you don’t go tagging people in couple-y meal shots if you’re not serious. And I know I could be misinterpreting the photos but I can’t keep kidding myself, this has got to stop. So I believe that this is what’s happening and bear down. I’ve been going on so many bad dates that I’ve been treating him like the last bastion of hope for my sex life. I cry myself to sleep.

The next day I feel remarkably fine with it. I realize that it wasn’t him; it was the sex. I was denying myself something I thought I could just order by picking up the phone, but that’s no longer an option. He’s with cute dinner-breakfast girl. He’s off the menu. And I would never go for someone else’s guy. I feel liberated and also a little stupid for making such a big deal out of him. But I realize I need to go easy on myself since this is the first person I’ve slept with since my big break up.

The next week I see him on the street walking right beside me. This time I look the other way.