Serial Dater: Internet (Serial) Dater

by: Adam Guerino 

Serial Dater is a dating column chronicling a twenty-something gay male’s relationship with his addiction to dating. Throughout the series so far, the author quit dating and has recently tried to re-approach it with lessons learned from his abstinence.

If I’m serious about dating, I should, (pardon the cliche,) put myself “out there.” Or at least in a way that doesn’t directly apply to my pelvis. So, like writing a classifieds ad for love, I got an OKCupid account. Boyfriend position available, enquire within. Or, perhaps more apt: Help Wanted. If you’re not familiar with the site, it’s a free dating site where you upload pictures, fill out your basic information and answer compatibility questions. The compatibility questions is all that really separates this site from being facebook. With each question, such as “What’s a good first date?” you answer it then list what you want other people to answer and how important it is for them to answer the way you want them to. For example, I might answer “Coffee” and then say I don’t want to go on a date with someone who answers “Bath house.” With me so far?

Question: Are you ready to feel like a lab rat?

The whole thing is sort of demoralizing. Not from a sense of superiority but because setting up a profile is like dating yourself. You’re asking questions as though you were on a date but you’re only asking yourself. It’s all a bit schizophrenic. Or, worse, it’s like presenting to a mirror where you’re blowing kisses and winking at your reflection. Sure, I see the long-term goal but it’s still strange. It’s a good thing I hate talking about myself (see also: every Serial Dater.)

Question: Are you cynical and jaded?

As I filled out more and more questionnaires, I wondered about the context of previous relationships. The ones that worked well weren’t because we felt the same way about everything. And some of the worst relationships I’ve had were people I had a lot in common with. I was made all the more skeptical when I’d see people I had already dated on the site. (Don’t look so surprised, I’m a serial dater, remember?) Some of the better dates I’ve had were with people that OKCupid said I wouldn’t get along with and vice versa. This wasn’t always the case, often there’d be a high match and I realized I already dated them and fucked it up or I’d see a low match and wished I could have read their OKCupid profiles before I accidentally slept with them.

Question: Are you close with any of your exes?

And, of course, my worst relationship ever (I know that’s presumptuous but aside from dating someone who was into sticking rusty nails up my anus, I’m pretty sure I won’t date worse,) Rock Bottom was on the site. In fact, the site sent me a message saying “We think you’d like him.” It was terrifying, like a horror movie where you run as fast as you can and think you lost the killer but just as soon as you get to the boat-house/cabin/what-have-you and close the door behind you, he’s already in the room.

Question: Have you ever had a relationship last over a year?

Then I think about how first impressions and serendipity has ruled over my dating life thus far. How much I’ve liked some people was in direct proportion to how little I knew them. Maybe I shouldn’t think about online dating as a vessel to send me people to date but as a way to skip the first date; an elimination process to narrow down who has long term potential. Sure, I might have really enjoyed a first date with some of the guys that I wasn’t compatible with but I wouldn’t have enjoyed a relationship.

Question: What are you so scared of?

As per usual, I have doubts about dating. Who doesn’t? That’s a large part of why I jump into relationships, if I have time to over-think something, I’ll do so and the spiral of doubts will damn it. But maybe jumping right into something that’s a bit more logical is a smart compromise? I’ll try this whole “similar interests and goals” route instead of my usual “dick then date” approach. But if it doesn’t work then I know the future will be my website “” (Website pending.)

Adam Guerino is a writer in Chicago who works nationally as a stand-up comedian and event producer. He is the creator of OutLoud Chicago which brings queer entertainment to the mainstream. He will be reading an unpublished piece at Word Is Out a spoken word night presented by and OutLoud Chicago May 15th at Town Hall Pub 3340 N Halsted, 8pm. Admission is $5 and includes a companion lit zine. For more from Adam Guerino, is a great place to start.


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