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

48 Hours on OkCupid: The Good, The Bad, and The Creepylow cost IUI

So, diving into the world of online dating wasn’t exactly on my to-do list, but here we are! After a blissful year of being single—where my main focus was on my Netflix queue and curling up with my cats—my friends convinced me to give OkCupid a whirl. I had sworn off dating after a messy divorce and a four-year relationship that went about as well as a flat tire.

When my ex and I parted ways a year ago, I was all set to adopt more feline friends and take up hobbies like tennis and crocheting. Spoiler alert: I nailed the tennis part and even crafted a lovely scarf (still holding off on the cat parade). I spent quality time with my kids, reconnected with old pals, and tackled that towering stack of unread books. Life was good, but let’s be honest—I was missing the fun factor.

After a friend couldn’t stop gushing about OkCupid, I figured, why not? I thought I’d have a few low-stakes outings and see where it goes. Signing up on a lazy Sunday afternoon, I managed to upload a pic and pick a username before heading out for the day. Returning home, I found a whopping eight messages and 78 likes. All this from a slightly blurry photo of me—minus the kids—and my age. Talk about deep connections! The messages varied from sweet (“You have a beautiful smile! I’d love to get to know you”) to downright bizarre (“Hey sexy, when can we hang out?”).

I decided to spice up my profile with a few more photos and began the endless questionnaire OkCupid offers to refine its matchmaking magic. The questions started innocently enough (“Could you date someone who is messy?”) and escalated to the alarmingly personal (“How often do you masturbate?”). Thankfully, you can skip the ones that make you squirm; I tackled about 30 and left at least a dozen unanswered.

By bedtime, my inbox had filled up with another 10 messages—most of which seemed to be from guys who hadn’t even glanced at my profile. Even more puzzling was that many of these fellas had a 50% or higher “Enemy” rating, meaning we had vastly different answers to those match questions. I noticed plenty of guys with whom I had high compatibility ratings, so why were my “enemies” the only ones messaging me?

Monday rolled around, bringing even more messages (one delightful note from a gentleman named Tom ended with “Tom cares”) and an additional 50 likes. I learned that a “like” is basically a green light to chat if both parties reciprocate. I liked a handful of profiles and managed to snag a match with a single dad who digs music. Score!

As fate would have it, while browsing through profiles of strong matches, I stumbled upon a familiar face from college. We hadn’t really interacted back then, but we shared a lot of interests. I shot him a quick message, and to my surprise, he replied almost immediately. We set up a plan to grab drinks a few days later. Was it a date? Hard to say, but I was intrigued.

Determined to give this dating scene a fair shake, I messaged the single dad and a few other guys who didn’t seem like they’d auditioned for a horror film. Unlike the creepy messages flooding my inbox, I tried to inject some wit and relevance into my outreach. Only the single dad responded, and while he seemed nice, the back-and-forth started to feel tiresome.

Fast forward to the next day: I racked up over 200 likes and 43 messages. Flattering, sure, but the lack of genuine effort from these admirers began to wear on my patience. I understand online dating can be a numbers game—send out 20 messages, get a few responses, and maybe one will lead to a real date—but I was losing interest.

After receiving a series of increasingly unsettling messages from a particular gentleman, I decided to take a breather and disable my profile. I’m certain there are decent guys on OkCupid—my college friend is living proof of that, as is a buddy of his who just married the first woman he met on the site—but I wasn’t finding my connections there.

Ultimately, my brief adventure on OkCupid wasn’t a total bust. That date with my college acquaintance went surprisingly well, and it felt like an actual date! Thank goodness I wore my cute heels. He’s even whipping up dinner for me this weekend. Plus, I found the whole experience to be a fascinating social experiment.

Here’s what I learned in my short time on OkCupid:

  • Men in their 40s typically gravitate toward women 10-15 years younger. Understandable, considering many of these guys, including my college friend, are looking to settle down and start families.
  • Guys of all ages seem to believe women are solely interested in their six-pack abs and well-defined pecs. Gentlemen, if I want to see you naked, I promise you’ll be the first to know. Until then, keep those shirts on!
  • Sixty-something men with beards find me particularly appealing. While there are perks to dating older (or younger) men, I’m sticking with those closer to my age—beards can be optional.
  • Many men don’t pay attention to what you say you’re looking for or whether the algorithm indicates compatibility. If you respond, you’re suddenly considered a match.

I’m not giving up on online dating entirely. There’s something thrilling about the idea of connecting with other singles on the hunt for their perfect match (or a fun night out). However, I might prefer a platform like Coffee Meets Bagel, which sends you one match per day and limits profile browsing until you’ve liked someone.

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