48 Hours on OkCupid: The Pros, Cons, and Unsettling Encounters

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My foray into OkCupid was not exactly a meticulously planned endeavor. After a fulfilling year of being single and largely uninterested in dating, I had resisted the attempts of friends and family to play matchmaker. The thought of dating felt utterly draining. Following a long-term relationship that ended in divorce and another four years with someone who was clearly not a good fit, I was ready to take a break. My post-breakup plan involved adopting more cats and picking up hobbies like tennis and crocheting—both of which I successfully pursued. I even crafted a scarf and joined a doubles tennis league, all while enjoying quality time with my children, reconnecting with old friends, and finally tackling that mountain of unread books.

Life was indeed pleasant, though I realized it lacked a certain excitement. Encouraged by a friend’s enthusiastic recommendation of OkCupid, I decided to dip my toes into the dating pool, aiming to meet new people without any serious intentions.

I began the registration process one Sunday afternoon, just before heading out for a few hours. With limited time, I selected a username and uploaded a single photo. Upon returning home, I was greeted by eight messages and an astonishing 78 likes, all based on a fuzzy image of myself without my kids and my age. The messages ranged from genuine compliments to some that were decidedly unsettling.

After adding more photos and completing a series of questions designed to fine-tune the matching algorithm, I encountered inquiries that escalated from benign to highly personal, such as “How often do you engage in self-pleasure?” Fortunately, I could skip any questions I found too intrusive. I answered about 30 and opted out of at least a dozen.

By the time I went to bed, my inbox held another 10 messages, most of which appeared to be from individuals who hadn’t bothered to read my profile. Interestingly, many of these messages came from users with a 50 percent or higher “Enemy” ranking, indicating that our preferences clashed. Despite seeing several profiles with high compatibility ratings, it seemed that only those labeled as “enemies” were reaching out.

Monday morning brought a fresh wave of messages, including a particularly charming one from an older gentleman named Thomas, who signed off with “Thomas cares.” I also discovered the concept of “likes”—if you click like on someone’s profile and they like you back, you receive a notification encouraging you to connect. I liked a few profiles and managed to score a match with a single father who shared my interest in music. I made a note to reach out to him.

An exciting turn of events occurred when I stumbled upon a familiar face from my college days. We had been in the same cohort but hadn’t interacted much. After perusing his profile, which revealed shared interests, I sent a brief message to reconnect. He responded promptly, and we arranged to meet for drinks a few days later—it felt like a date, though I wasn’t entirely certain.

Determined to give dating a fair chance, I reached out to the single dad and three other potential matches who didn’t come off as potential serial killers. Unlike the generic messages I was receiving, I aimed to craft messages that were engaging and relevant. Only the single father responded, and while we exchanged a few pleasant emails, I sensed a lack of urgency on his part to meet in person.

By the following day, I had amassed over 200 likes and 43 messages. While flattering, the superficiality of my admirers began to grate on my nerves. I understood the nature of online dating as a numbers game—send out many messages to garner a few responses, but I was starting to question whether the effort was worthwhile.

After receiving a series of increasingly unsettling messages, I opted to disable my profile for a time. While I’m sure there are genuinely nice individuals on OkCupid—my college connection is proof of that—I wasn’t making the right connections.

Despite my mixed experience, my first date with Thomas went exceedingly well, feeling very much like a genuine date. Thankfully, I chose to wear heels. He has plans to prepare dinner for me this weekend. Additionally, my brief stint on OkCupid provided some intriguing insights into the dating landscape.

Key Takeaways from My Experience

  1. Men in their forties often prefer dating women 10-15 years their junior, likely due to aspirations for marriage and family.
  2. Men of all ages seem to believe that women are primarily interested in their physical attributes; a gentle reminder for them—if I wish to see you naked, I promise I will let you know.
  3. Older men with beards appear to find me particularly appealing, but I prefer to date those closer to my own age—beards optional.
  4. Many men seem oblivious to the preferences outlined in my profile or the compatibility ratings provided by the algorithm; if you reply, you’re considered a match.

I remain open to online dating, as the prospect of meeting other singles is undeniably thrilling. However, platforms like Coffee Meets Bagel, which offers one match per day and restricts access to contacts unless there’s mutual interest, may better suit my needs.

In summary, my brief adventure with OkCupid was a mixed bag of encounters—ranging from promising to downright creepy. While I did manage to connect with a former acquaintance from college, the overall experience underscored the challenges and peculiarities of online dating.

Keyphrase: OkCupid Dating Experience

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