Why I Internet Date

“Hey dude, why the heck are you still internet dating?”

I get that question at least once a week friends, twice a week from my shrink, and I’m pretty sure my cat has been building up the courage to ask for a few years now. It’s a reasonable question. Why, after too many terrible dates to count, and only a handful of encounters that can reasonably be deemed successes, am I still trying to meet people online? I mean, if every time you opened your front door, a guy hit you in the face with a hammer, you’d probably stop opening the front door, right? Not me. I just keep running into that hammer over and over again. I do it because, first of all, the economy’s bad, and who am I to pull front-door hammer guy’s job out from under him? And second, I stick with internet dating because I’ve found traditional dating to be no less brutal, complex, and fraught with disappointment. Am I leading up to story? Yes, yes, I am…

Several years ago, I worked for an internet company. Not one of the really good internet companies, like Google or Amazon or ThisIsWhyImBroke.com, that provide an important service to the world. No, I worked for a website that sold decorative roosters made from grass and dried hay. That wasn’t our only product of course, you can’t build an entire company on poultry crafts alone. We also sold tea cozies made to look like Scooby Doo’s head, and toilet plungers that had sparkly streamers sprouting out of pink polka-dotted handles. Because America’s number one complaint about the toilet plunger has always been its lack of pizzazz. In a general sense, my website sold gifts; but only the sort of gifts you give someone the moment before you tell them you never wanted to see them again. “Here’s a rooster, now scram.” My job was to write the copy describing these gifts, and it was easily the worst job I’ve ever had.

One day, however, a new girl arrived at the office. Until then, my co-workers at this website, let’s call it AwfulGifts.com, had been made up primarily of deeply religious Filipinos and older gay men. Needless to say, I was not exactly knee-deep in romantic opportunities at work, or even conversation-based-on-vaguely-similar-interest opportunities. And then, Tracy arrived. Tracy was two years younger than me, equipped with a quiet but wicked sense of humor, and cute as a button. OK, fine, a button with spectacular breasts, if you’re going to twist my arm for details. But Tracy and I, well, we hit it off.

Quickly, we established our own flirty little rhythm. I’d get up to get some coffee, and Tracy would walk over and ask if I had heard the new Mountain Goats album. Then we’d joke and banter and joke and banter until someone who had more power than us gave us a look that said, “Get back to work, you hippies.” Tracy would get up to go to lunch, and I’d ask if she wanted help stealing extra samples from Wholefoods. The CEO would call us all in for a big meeting, and Tracy and I would compete to see who could most convincingly pretend to throw up in the garbage can. (Winner: Me. Loser: Also Me.) You’ve had office flirtations, you know how it goes, I don’t need to spell this all out for you. It starts with the simple discovery of someone who helps the day go by quicker. Then, a few months later, you find yourself actually looking forward to going to work everyday and you realize, “Ooooh boy. I’m in too deep.” And then you’ve got a problem on your hands.

Because office romances are complex, and because I’m, deep down, a buffoon, Tracy and I lingered in the flirty-friendy-datey-paly stage for way too long. Like… two months too long. And that can be hard to come back from. I had started seeing her outside of the office, but they were never clearly dates. They were flirty hangouts, and they never ended with a kiss. So I decided to get serious. One Friday afternoon, I decided that that weekend would be the time. I would ask Tracy out, and at the end of that date I would kiss her. Come hell or high water or charges of sexual impropriety. So as I sat working at my desk, carefully crafting descriptions of necklaces hand-designed by blind nuns in exile, I plotted my maneuvers. Do I do it at lunch, or over coffee? Should I send Tracy her a cutesy email with a MacPaint caricature of our CEO in the bathtub, or should I do it face-to-face? Just as I thought I had it all figured out, I looked up and found Tracy standing in front of my desk, with an awkward smile.

Tracy: Looks like it’s gonna snow this weekend. Wanna go sledding in Central Park?

Brian (cool as a cucumber): Wha… uh… oh… yeah? Yeah! Of course I do. Sounds fun!

And there it was! She asked me out! And what could be cuter and sweeter and more romantic than a lovely little sledding date? It was far better than anything I could’ve crafted myself — playful and fun, while still rich with datey potential. She would zip down a hill, then stumble on her way back up. I would rush to help her, then we would fall into a tender embrace. I’ll take two tickets to Smooch City, please. Or how about a jovial little snowball fight? That’s something people do, right? We’d toss snowballs at each other, then break into hysterics when we accidentally hit a passerby.

Then we’d screw. Just screw and screw and screw. It was all coming together!

I arrived at Central Park on Sunday while the snow was still falling. Kids were everywhere, the ground was covered in fresh powder, it was a date that would’ve given Norman Rockwell a boner. I saw Tracy standing on one of the big hills, looking adorable as she plotted out the best place to sled. It was so perfect that I considered running to her and kissing her right then and there… until I saw him. As I approached though, it seemed that Tracy was talking to someone. A guy our age, who looked to be pointing out the best angles for top velocity. I waved to her, and both she and her companion waved back. Hmm, it appeared that Tracy brought a friend.

His name was Bryce, and he certainly had a flair for sledding. He took running strides before launching onto his innertube, zipping dangerously close to five different kids’ heads. He sled in blue jeans, sneakers, and a thin, apparently ironic Member’s Only jacket. He was what my college Theology teacher used to call a Hipster Doofus, and nobody embodied it better than Bryce. I mean come on, sledding in sneakers? Is it really worth it?

Although Bryce’s presence meant I would have to work a little harder to find a moment to sneak a kiss from Tracy, it was fine to have another along for the snow day fun. Perhaps he could be our first couple friend! We took turns sliding down the hill on our one innertube. The sledding was fun, but I most looked forward to Bryce’s turn on the slopes, so I could stay with Tracy and throw a little love kindling on the chemistry fire. (Don’t worry, I didn’t say these things aloud.) It was a little awkward, she seemed kinda distracted, but I was sure it was just the romantic tension getting to her. It had been several months of flirtation leading up to this one big day. As it was nearing the end of the afternoon, Bryce stomped up the hill and handed me the innertube.

Bryce: One last ride down the hell mountain, good man?

This was how he talked. Hipster doofus, am I right? I accepted the sled and jumped down the hill, but halfway down hit a patch of ice. The tube spun around wildly, and then flipped over, tossing me out into the snow. It hurt like hell, but I was sure to get up with a smile, just in case Tracy was watching. When I looked back up to the hill however, it was clear that I didn’t have to worry about Tracy judging my awkward fall. There was no way she could have seen it, because at the moment Tracy was giving her entire attention to kissing the living shit out of her pal Bryce.

After that I did what any self-respecting man would do, I told the pair that I wasn’t feeling well and went home. A few days later I confronted Tracy about the situation and she apologized for not telling me about Bryce, who she’d been dating for… wait for it… the last six months. I told her I understood, that it can be hard to find just the right way to bring up your boyfriend to the other guy you were out on a date with. She felt terrible, but at that point it really didn’t matter. It was clear that Tracy did in fact like me, but had gotten herself into a situation far more complicated than she could handle. I was angry with her, she grew uncomfortable with me, and as happens with many office romances, everyone involved wished they were just somewhere else. Even the Filipinos and gay dudes. Mercifully then, Tracy announced she was moving to California a few months later, and I wasn’t unhappy to see her go.

Is internet dating better than traditional dating? I haven’t the slightest idea. No matter what platform you’re using, dating people still involves people — whether you meet them on the computer, in a coffee shop, or at the desk next to yours in the most ridiculous internet company on earth. And people, sometimes, suck. At least when you meet ‘em online, you know they’re actually single and looking to date. Well, most of the time, anyway. But one thing you do know is, that if they break your heart, you’ll never have to see them again. And that kinda knowledge, well that’s worth a whole bushel of dehydrated roosters. TC mark

image – Shutterstock


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  • http://twitter.com/ninjatek Chris Leher (@ninjatek)

    Just have to say I met my Fiance off of OkCupid 4 years ago, met up just for a hookup, but instead fell in love.

  • http://gravatar.com/scenefromahat Jessica

    i see the girl i used to date and am still in love with everyday at work :/ we both love our jobs too much to leave. i am still on okcupid like a horndog and although almost all of my okcupid dates have been good, it still feels weird. but not at the same time. i don’t know.

    • http://thebriandonovan.wordpress.com Brian Donovan

      That sounds deeply awful. I think you love your job more than I I love any job ever.

  • http://twoseconds.tumblr.com jesse v

    Very good read, but seriously, ‘ it was a date that would’ve given Norman Rockwell a boner’ wins everything today.

  • caroline

    this guy is exactly why i don’t internet date. the dude who dances around, waiting for a woman to one day magically figure out that he’s into her… lord….

    • http://thebriandonovan.wordpress.com Brian Donovan

      Thanks for the support, Caroline!

    • Nick

      If it’s a dating site and he’s paying you attention, he’s into you. Why else would he be communicating with you? PS If it’s real life, then the “dancing” in the article is often due to not knowing the answers to the questions “is she a Bryce-free heterosexual?” and “will my ‘going there’ make future interactions awkward (at work, school, laundromat, etc) for both of us?”

  • Christina

    I read this article somewhere else before. Exactly the same story, almost word for word.

  • http://gravatar.com/mpiotro2 Maggie

    Sounds like 500 Days of Summer… minus the middle, and plus a crappy day of sledding.

    • http://thebriandonovan.wordpress.com Brian Donovan

      500 Days of Winter would’ve been a good title, actually. Rats.

  • http://gravatar.com/casssadaga Meg

    Gotta say, absolutely hated okcupid and all of my meet-ups ended dismal, but I did find my current boyfriend via tumblr…actually, via a friend I met on tumblr. We became good friends and it just sort of happened. If I am to meet some via interwebs, I’m happy it happened the way it did. Just as much as a surprise in the real world as in the internet world. :)

  • http://okweirdo.com raymondthimmes

    I find it almost impossible to figure out when a chick is into me or when she’s just being nice. Been here, my friend. Too many times.

    • Nick

      The ladies often don’t understand the risks that fellas take. We don’t truly know what she thinks of us til we start grabbing cooch. Sounds crass, but think about it. Even this story illustrates the possibility that rudely bringing your boyfriend unannounced on an outing with another dude can *still* indicate *possible* interest in some sick way.

      • http://thebriandonovan.wordpress.com Brian Donovan

        I’m getting “You Don’t Know What She Until You Start Grabbing Cooch” made into a t-shirt.

    • CC

      If men had the initiative and risk tolerance of women, we’d have gone extinct long ago. You’re welcome.

      • Hayley

        On behalf of all women, THANKS!!! You’re the best! Go you! Yay!

  • H

    Does everyone have a therapist now?

  • Nick

    Men & women are people, and people tend to want the same things. If you would respond positively if the other person did x, y, & z for you, then do x, y, & z for the other person. The golden rule is often quoted and rarely followed. I can’t think of a good reason to wait on the other person other than cowardice. They’ll either appreciate it or you’ll know to move on. The 3 keys to relationship success (since I’m so successful–not :) are 1) ask what the other person wants and give it to them; 2) tell the other person honestly (whether asked or not) what you want and expect it from them; and 3) negotiate 1 & 2 constructively without threats (e.g. don’t use “I think we should break up” as a bargaining chip or conversation opener to avoid saying what you want for the first time). My 3 cents.

  • Nick

    Brian, sell the shirt on awfulgifts.com. Send my cut to themmrf.org. Holla!

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