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

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So, I decided to jump into the world of OkCupid without much thought. After a year of being happily single, I had pretty much ignored any attempts by friends and family to set me up on dates. Honestly, dating felt like a chore—after a long relationship that ended in divorce and another one that was just wrong for me, I was over it. My plan post-breakup was to adopt a few more cats, take up tennis, and maybe try crocheting. And that plan worked out well! I got good enough at tennis to join a doubles league, made a cozy scarf, and even managed to take some fun trips with my kids and reconnect with old friends.

But while life was pleasant, I realized I wasn’t having much fun. After hearing a friend rave about OkCupid, I thought, why not? I could go on a few dates and meet some new faces—nothing too serious.

I kicked off the sign-up on a Sunday afternoon, just before heading out for a few hours. I picked a username and uploaded a photo, and by the time I got home, I had eight messages and 78 likes—all based on a blurry picture of me with my kids cropped out, my age, and my username. Talk about deep connections! The messages ranged from sweet (“What a beautiful smile! I’d love to get to know you”) to downright creepy (“Hey sexy, when can I come over?”).

After adding more photos, I dove into the endless questions OkCupid asks to match you with potential dates. They started off innocently enough, like “Could you date someone who is messy?” but quickly escalated to the personal (“How often do you masturbate?”). Thankfully, you can skip questions you’re not comfortable answering. I managed to answer about 30 and skipped a dozen more.

By the time I hit the pillow, I had received another 10 messages. It felt like none of these guys had even glanced at my profile. Even more puzzling was that most of them had a 50 percent or higher “Enemy” ranking, suggesting we had opposing answers to the match questions. I noticed plenty of guys with high match ratings, so why were these so-called enemies the only ones reaching out?

Monday morning brought a fresh wave of messages (the best one came from a gentleman named Tom, who signed off with “Tom cares”) and another 50 likes. I figured out that a “like” means if someone you like also likes you back, you get a little pop-up prompting you to reach out. I liked a few profiles and got one match—a single dad who enjoys music. Not too shabby! I made a mental note to message him later.

A pleasant surprise came when I stumbled across a familiar face from college. We were in the same class but hadn’t really connected back then. After browsing his profile, it seemed we had a lot in common, so I sent him a quick message saying, “Hey, I think we know each other,” and headed off to work. He replied promptly, and we arranged to meet for drinks a few days later. I was excited yet unsure if it was a date or just two old acquaintances catching up.

Determined to give this dating thing a fair shot, I messaged the single dad along with three other guys who seemed less likely to be serial killers. Unlike the messages I was getting, I put effort into mine, hoping they came across as fun and relevant. Only the single dad replied. We exchanged a few emails, and while he seemed nice, I felt the back and forth was dragging on without any real interest in meeting up.

The next day, I had racked up over 200 likes and 43 messages. Flattering? Sure. But the lack of effort from these admirers was wearing me down. I understood it was a numbers game—send out 20 messages, get a few responses, and maybe land a date—but I wasn’t sure I had the energy for that.

After receiving a series of increasingly creepy messages from one guy, I decided to hit pause on my profile. I know there are decent guys on OkCupid—my college friend is proof of that, and I have a friend who recently found love on the site—but I wasn’t connecting with them.

However, my time on OkCupid wasn’t completely wasted. My date with the college friend went well and felt genuinely like a date. Lucky for me, I wore heels. He’s cooking dinner for me this weekend! Plus, the whole experience was an interesting sociological experiment.

Lessons Learned

From my brief stint on OkCupid, I learned a few things:

• Many men in their 40s prefer dating women 10-15 years younger. I get it—some of these guys, my college friend included, are looking to settle down and start families, which is less likely with women their age.
• Men of all ages seem to think women are incredibly interested in their abs and other body parts. Guys, if I want to see you naked, you’ll definitely be the first to know. Until then, a little modesty goes a long way.
• Men in their 60s with beards apparently find me attractive. While there are perks to dating older (or younger) men, I think I’ll stick to those closer to my age—beards are optional.
• Guys often ignore what you say you’re looking for or whether the algorithm says you’re compatible. If you respond, you’re a match!

I’m not giving up on online dating just yet. There’s something exciting about knowing there are other singles out there looking for their Ms. Right (or Ms. Right for the Night). However, I think I might prefer a service like Coffee Meets Bagel, which sends you one match each day without the hassle of browsing profiles or getting contact info unless you like someone first.

In conclusion, while my time on OkCupid had its ups and downs, it was a valuable experience, and I might just explore a more curated approach to online dating next time.