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

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My foray into OkCupid wasn’t exactly a well-thought-out plan. After enjoying a year of singlehood without much thought about dating, I had managed to resist the matchmaking attempts of friends and family. The idea of dating felt overwhelmingly exhausting. After a 12-year marriage that ended in divorce and another four years with a partner who was completely wrong for me, I was content. Following my breakup a year ago, I envisioned a future filled with more cats, tennis, and crocheting.

And it worked out well. I picked up enough tennis skills to join a doubles league and even crocheted a scarf (the cat adoption will have to wait). I took trips with my kids, reconnected with old friends, and finally tackled that stack of unread books on my nightstand. Life was good, but I realized that while I was happy, I wasn’t exactly having fun.

When a friend praised OkCupid, I thought, why not? I figured I could go out on a few casual dates and possibly meet some new people. Nothing serious.

I began the sign-up process on a Sunday afternoon, just before heading out for a few hours. I had just enough time to select a user name and upload a picture. To my surprise, when I returned home, I had eight messages and 78 likes—all based on a blurry photo of me with my kids cropped out, my age, and my user name. Talk about deep connections! The messages ranged from sweet (“You have a beautiful smile! I’d love to get to know you”) to downright creepy (“Hey gorgeous, when can I come over?”).

I uploaded more pictures and started answering the seemingly endless questions OkCupid provides to refine its matching algorithm. Initially, the questions were harmless (“Could you date someone who is messy?”), but soon escalated to the extremely personal (“How often do you, um, you know?”). Thankfully, I could skip any that made me uncomfortable. I tackled about 30 questions and skipped at least a dozen.

By the time I went to bed, I had received another 10 messages. It seemed like none of these guys had actually read my profile. Even more bizarre, many of them had a 50 percent or higher “Enemy” ranking—indicating we had opposing answers to the matching questions. I noticed plenty of guys with whom I had high compatibility ratings, so why were all my so-called enemies the only ones messaging me?

Monday morning brought even more messages (one particularly memorable one was from an older gentleman named Bill, who signed off with “Bill cares”) and another 50 likes. What exactly is a “like”? Well, if you click like on someone’s profile and they reciprocate, you get a pop-up encouraging you to reach out. I “liked” four or five profiles and got one match—a single dad who loves music. Promising! I mentally noted to message him.

Then I stumbled upon an unexpected surprise. While browsing profiles of men who matched well with me, I found a guy from college. We were in the same freshman class but had never really connected. After scanning through his profile, I noticed we had a lot in common. I sent him a quick message, “Hey, I think we know each other,” and headed off to work.

He replied almost instantly, and we set plans to grab drinks in a few days. Exciting, though I wasn’t entirely sure if it was a date or just a catch-up with an old acquaintance. If I was going to give this dating thing a fair shot, I decided to reach out to the guy who had liked me, along with three others who seemed less likely to be serial killers. Unlike the generic messages I was receiving, I put effort into mine to make them engaging and relevant. Only the single dad replied. We exchanged a few emails, and while he seemed nice, I grew weary of the back-and-forth and didn’t sense he wanted to meet up in person.

By the next day, I had accumulated over 200 likes and 43 messages. While flattering, the lack of depth and effort from my admirers was draining. I understood it was a numbers game—send out 20 messages, get three or four replies, and maybe one could lead to a real-life date—but I was beginning to question whether I was motivated enough to keep at it.

After receiving a series of increasingly unsettling messages from one gentleman, I decided to take a break from my profile. I’m sure there are nice guys on OkCupid—my college friend is proof of that, as is a friend of his who recently tied the knot with the first woman he met through the site—but I just wasn’t connecting with them.

OkCupid wasn’t a total waste. My first date with my college friend went well and definitely felt like a date. Good thing I wore heels! He’s cooking dinner for me this weekend. Plus, my brief experience on OkCupid turned out to be an interesting sociological experiment. Here’s what I learned:

  • Men in their forties typically seek women 10-15 years younger. This makes sense; many of these guys, including my college friend, are looking to marry and have kids, which is less likely with women their age.
  • Men of all ages seem to think women are intensely interested in their abs, pecs, and, well, other body parts. Guys, take note: If I want to see you naked, you will be the first to know. Until then, cover up.
  • Sixty-something men with beards apparently find me quite appealing. While there are reasons to date older (or younger) men, I prefer to stick with guys closer to my own age—beards are optional.
  • Men don’t pay attention to what you’re looking for or whether the algorithm shows compatibility. If you respond, you’re a match in their eyes.

I’m not giving up on online dating just yet. There’s something thrilling about knowing there are numerous other singles out there searching for their Ms. Right (or Ms. Right for the Night). However, I think a platform like Coffee Meets Bagel, which offers one match a day and doesn’t allow users to browse profiles or access contact information unless there’s mutual interest, might suit me better.

For more insights on this subject, feel free to check out this blog post that dives deeper into the world of online dating.

In summary, my brief experience on OkCupid was eye-opening, revealing both the excitement and the challenges of dating in the digital age. If you’re considering home insemination, I recommend visiting CDC’s pregnancy resource for valuable information. For at-home insemination kits, check out this reputable site to find what you need.


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