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

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My foray into the world of OkCupid was not a thoroughly planned endeavor. After a fulfilling year of singlehood, I had almost completely detached from romantic pursuits, even ignoring attempts by friends and family to set me up. The idea of dating felt overwhelming. Following a 12-year marriage that ended in divorce and an additional four years with an unsuitable partner, I had resolved to focus on self-care. My post-breakup plans revolved around adopting more cats and exploring hobbies like tennis and crocheting.

And I succeeded. I honed my tennis skills sufficiently to join a doubles league and even crafted a scarf—though I postponed expanding my feline family for the time being. I relished in quality moments with my children, reconnected with old friends, and tackled a stack of unread books. Life was enjoyable, albeit lacking in excitement.

Upon hearing a friend’s enthusiastic endorsement of OkCupid, I decided to give it a shot. My intention was simple: to meet new people and potentially go on a few casual dates. I began the registration process on a Sunday afternoon, just before heading out, allowing myself time to choose a username and upload a photo.

Returning home, I found myself inundated with eight messages and 78 likes, all generated from a blurry image of myself absent of my children, my age, and my username. The messages varied from genuine compliments (“You have a lovely smile! I’d like to get to know you.”) to rather unsettling propositions (“Hey gorgeous, when can I come over?”).

I proceeded to add more photos and delved into the extensive questionnaire OkCupid provides to refine its matching algorithm. The initial questions were innocuous enough (“Could you date someone who is messy?”), but they soon escalated to highly personal inquiries (“How often do you engage in self-pleasure?”). Thankfully, there’s an option to skip questions that feel too intrusive. I answered about 30 questions, opting out of at least a dozen.

By the end of the night, I had received another 10 messages, most of which seemed to come from individuals who hadn’t even glanced at my profile. Notably, many of these individuals had a “50 percent Enemy” rating, implying our answers to the matching questions were at odds. Despite my browsing revealing several men with high compatibility ratings, it appeared that only my so-called enemies were reaching out.

Monday morning brought yet more messages, including a charming one from a gentleman named Mark, who signed off with, “Mark cares.” I also discovered that a “like” is a mutual acknowledgment: if you express interest in someone who reciprocates, you receive a prompt encouraging contact. I liked a handful of profiles and managed to match with a single dad passionate about music. A promising start!

While exploring profiles of potential high matches, I stumbled across a familiar face from my college days. We shared the same entering class but had never interacted much. After scanning his profile, I found common interests and sent him a casual message, “Hey, I think we might know each other.” He responded promptly, and we arranged to meet for drinks a few days later. This was exciting, though I was uncertain if it was a genuine date or merely two former classmates catching up.

Determined to give dating a fair chance, I reached out to the single dad and three others who seemed less likely to be serial killers. Unlike the messages I received, I aimed to craft thoughtful and engaging notes. Only the single dad responded, and while our email exchanges were pleasant, I sensed a lack of urgency on his part to transition to an in-person meeting.

By the following day, I had accumulated over 200 likes and 43 messages. While flattering, the superficiality and minimal effort from my admirers were starting to wear thin. I understood that online dating can be a numbers game—sending out numerous messages in hopes of receiving a few replies—but I questioned whether I was willing to exert that effort.

After receiving a series of increasingly unsettling messages from one individual, I decided to temporarily deactivate my profile. I believed there were genuinely nice individuals on OkCupid—my college acquaintance being one example—but I simply wasn’t connecting with them.

Despite the challenges, my experience wasn’t entirely negative. My first date with Mark went remarkably well and felt genuinely like a date. Thankfully, I wore heels. He’s preparing dinner for me this weekend, and my time on OkCupid has proven to be an intriguing social experiment.

Lessons Learned

From my brief experience, I learned a few things:

  • Many men in their forties often seek women 10-15 years younger; this is understandable as they may desire to marry and have children, which is less likely with women their own age.
  • Men of varying ages seem to believe that women are intensely interested in their physique. Gentlemen, if I wish to see you undressed, I assure you, I will let you know. Until then, please keep your clothes on.
  • Older men, particularly those in their sixties with facial hair, appear to find me quite appealing. While there are merits to dating across age groups, I prefer to stay within my own age bracket—beards are optional.
  • Many men do not heed the specifications outlined in profiles regarding what individuals seek in a partner or whether there is compatibility according to the algorithm. If you respond, you’re considered a match.

I remain open to online dating, as it’s exhilarating to know that numerous other singles are seeking their Ms. Right (or Right for the Night). However, I believe a service like Coffee Meets Bagel, which offers one curated match daily without allowing users to browse profiles or access contact information unless both parties express interest, may align more with my preferences.

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In summary, navigating online dating can be both enlightening and perplexing, revealing insights about personal preferences and societal trends. While it may not be a perfect fit, the experience can lead to meaningful connections and opportunities for growth.

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