48 Hours on OkCupid: The Good, The Bad, and The Creepy

My decision to give OkCupid a try wasn’t exactly well-considered. I’ve been happily single for the past year, with nary a thought to men. I didn’t even bite when friends and family tried to set me up.

Dating just seemed…exhausting. After 12 years in a relationship that ended in divorce and another four with someone who couldn’t have been more wrong for me, I was done. When the ex-BF and I split a year ago, my plan was to add a few more cats to my collection and take up tennis and crocheting.

And it worked. I learned to play tennis well enough to join a doubles league, and I am the proud owner of a scarf I crocheted myself (decided to postpone the cat influx). Best of all, I took some trips with my kids, caught up with old friends, and tackled a stack of books that had been gathering dust on the nightstand.

Life was good, but, while I was happy, I wasn’t having all that much fun.

So after a friend raved about OkCupid, I decided to give the dating site a try. I figured I’d go out on a few dates, meet some new people. Nothing serious.

I started the sign-up process on Sunday afternoon, right before heading out for a few hours. I had just enough time to pick a user name and upload a photo.

I came home to eight messages and 78 likes—all based on a fuzzy photo of me with my kids cropped out, my age, and my user name. Deep connections there. The messages ranged from sincere (“Beautiful smile! I’d really like to get to know you”) to creepy (“Hey sexy, when can I come over?”).

I added a few more pics and started answering the seemingly endless questions OkCupid asks to determine its matching algorithm. They started out harmless enough (“Could you date someone who is messy?”) but quickly progressed to the extremely personal (“How often do you masturbate?”). Fortunately you can skip ones you’d rather not answer. I answered about 30, and skipped at least a dozen.

By the time I went to bed, I’d gotten another 10 messages. None of them had bothered to read my profile as far as I could tell.

Even more interesting, most of them showed a 50 percent or higher “Enemy” ranking, which, as far as I can tell, means we had opposing answers to the match questions. From browsing the site, I saw plenty of guys with whom I had high match ratings, so why were all my so-called enemies the only ones I was hearing from?

Monday morning brought even more messages (the best one, from an older gent named Richard, was signed, “Richard cares”) and another 50 likes. What is a “like”? Turns out if you click like on the profile of someone who also likes you back, you get a little pop-up encouraging you to get in touch. I “liked” four or five profiles and got one match, a single dad who’s into music. Promising! I made a mental note to email him.

I also got a nice surprise. While clicking through profiles of men who were listed as a strong match, I came across a guy I recognized from college. We had been in the same entering class, but hadn’t really known each other. I scanned through his profile and we seemed to have a lot in common. I sent him a quick, “Hey, I think we know each other” message and headed to work.

He replied right away and we made a plan to meet for drinks a few days later. Exciting, though I wasn’t 100 percent sure whether it was a date or just two acquaintances catching up.

If I was going to do this dating thing, I wanted to give it a fair shot. I messaged the guy who “liked” me along with three others who seemed unlikely to be serial killers. Unlike the messages I was getting, I worked hard on mine to make them (I hope) amusing and relevant. Only the single dad wrote back. We exchanged a few emails and he seemed nice enough, but I got tired of the back and forth and wasn’t getting any sense he was interested in meeting in person.

By the next day, I had racked up more than 200 likes and 43 messages. Flattering, sure, but the shallowness and total lack of effort my admirers were putting forth was wearing on me. I get that it’s a numbers game—for every 20 messages you send, you might get three or four back and maybe one of those could turn into a real-life date— but I wasn’t sure I cared enough to put in that kind of effort.

After getting a series of increasingly creepy messages from one gentleman, I decided to disable my profile for awhile. I’m sure there are some nice guys on OkCupid—my college friend is proof of that, as is a friend of his who recently married the first woman he met through the site—but I wasn’t connecting with them.

OkCupid wasn’t a total loss. The first date with my college friend went well, and did, indeed, feel like a date. Good thing I wore heels. He’s making dinner for me this weekend. And OkCupid was interesting as a sociological experiment.

What I gleaned from my short time on OkCupid is this:

· Fortyish men generally want to date women 10-15 years younger. I get this—many of these guys, my college friend included, would like to get married and have kids and that’s less likely to happen with women their age.

· Men of all ages think women are really, really interested in their abs, pecs, and, er, other body parts. Dudes, listen up: If I want to see you naked, I promise you will be the first to know. Until then, cover up.

· Sixtyish men with beards apparently find me really attractive. While there are reasons to date older (or younger) men, I’m sticking with guys closer to my age. Beards optional.

· Guys do not pay any attention to what you say you’re looking for or whether or not the algorithm shows you’re compatible. If you write back, you’re a match.

I’m not swearing off online dating. There’s definitely something exciting knowing there are lots of other single people out there looking for their Ms. Right (or their Ms. Right for the Night). But I think a service like Coffee Meets Bagel, a newer site that sends you one match per day—but doesn’t allow you to search profiles or get someone’s contact info unless you like them first—might be more my speed.