I had nothing to wear. So, I went out and bought something special for 10 and 10 Club’s first singles event, designed to bring together 10 men and 10 women for a night of “guided convos and games.” Local real estate agent and hospitality veteran Cara Bowman started the club mainly because of a single friend. “I think everyone’s frustrated with the apps,” Bowman says.
And the evidence is more than anecdotal—according to a Forbes Health survey this year, 78 percent of respondents reported experiencing dating fatigue “sometimes, often, or always.” That’s a pretty large number of burnt-out people when you consider that around 60 million people in the United States are using or have used online dating services.
As a 42-year-old woman, this feeling has resonated with me for some time. Single millennials are essentially aging out of the “fun zone” of dating and are now carrying more relationship baggage than in our 20s—me included.
But tonight was about holding onto hope and not letting the numbers affect my evening. My outfit was a little black number that was equal parts baby doll and ’90s slip dress. I paired it with frilly ankle socks and mules. I felt cute.
It has been three-and-a-half years since I’ve dated anyone, let alone felt attracted to someone. In that time, I’ve worked on myself and my career to become a more confident person and a better partner for someone someday. I was finally feeling ready to get back into the dating world, and the 10 and 10 Club seemed like the easiest way to get my feet wet.
When I arrived, I was greeted with an excellent soundtrack, a cheeseboard, and some social lubrication (thank god for Champagne) and started mingling for the first 30 minutes. During the night, we coursed through each of the three tables to ensure that everyone had the chance to meet. At these tables, we could ask each other questions from a printed list or play games such as flip cup.
The questions varied from mirthful to deep. My group chose to ask questions—our red Solo cup skills were pretty feeble, but our vulnerability game was on point. Well, everyone’s but mine.
I play things close to the chest. I’ve never been in a committed relationship, though I’ve experienced plenty of situationships and have been intimate with men I’ve found attractive along the way. So, when talk of “deal breakers” and “most romantic gestures” enters conversations, I tend to clam up. I feel like I have nothing to offer and don’t want to run the risk of looking stupid or inexperienced.
To a prospective suitor who wants something serious, I must look like a walking red flag. Why hasn’t anyone chosen her? What’s really wrong with her?
Despite my best efforts at sharing bits of myself and answering questions like What’s your worst injury? (falling off a bike in Germany hours into a hook-up vacation) and What would you change about society? (continue the trend of honoring mental health awareness), I didn’t make any connections with any of the men.
To be fair, no one was my type, so I didn’t engage with as much enthusiasm as I should have. In general, the crowd was attractive and well-adjusted, with interesting careers, insights, and the ability to crack jokes. This is not always the case with these types of mixers, so it was a nice surprise. By the end of the evening, some couples were even pairing off for deeper chats.
Before we parted ways, all participants received an envelope with notes from members of the group—anyone of the same sex interested in fostering a friendship or from the opposite sex looking for your digits. I got one. From the host of the event. I couldn’t help but feel like the chaperone was taking pity on the girl who didn’t get asked to dance. It’s uncomfortable enough trying to put yourself outside of a very cozy comfort zone only to be mocked by a lack of interest literally on paper. To be fair, other women and men got notes. Just not me. Perhaps the note passing is a humble lesson in, “You get what you put into it.”
But I forged on with my night and met up with some friends at a local karaoke bar. I approached a woman who sang Otis Redding’s “(Sittin’ On) The Dock of the Bay.” She was petite and friendly. She mentioned going somewhere else.
“Do you want to come?” she asked.
“Sure!” I replied, fortified by male rejection and a very strong Jell-O shot.
My friends tapered off. She and I walked alone to the next bar. We chatted about her tattoos and who we knew in the neighborhood. She drank a Dirty Shirley with two cherries.
We swayed on the dance floor to late-’70s no-wave bands. She inched closer, our hips attached, and she made her move. She kissed me, and I kissed her back. I knew people at the bar but couldn’t be bothered to care about them seeing. Kissing her felt nice and consequence-free—a low-stakes way to satisfy a long-standing curiosity. After the music died down and the lights came up, we moved it to my car for another make-out session, but that’s as far as it went. We exchanged Instagrams and I let her know that I got home safe. We haven’t talked to each other since.
I don’t take that as rejection. We had what we had.
What that night taught me is that maybe I’m not ready for something serious. And, quite frankly, that scares me. I denied a group of 10 eligible men who want a relationship for a random, cute woman with whom I know I have no future. Have I been unwittingly indoctrinated by my situationships to only be comfortable with a casual, surface-level hang? I know that, deep down, I want a serious relationship with a male partner.
Ultimately, though, I’m scared of being singular—not single. I’m scared that I don’t have enough to offer another person, that I’m vapid and uninteresting and the one person who is undateable and unloveable.
I’m afraid of being judged for who I am. Despite the many charming details of my personality, I’m afraid that no one will love my shadow qualities, from mental health issues to sloppiness and fiscal irresponsibility. I’m a 42-year-old relationship virgin without an Amex, who, more often than not, buys new underwear instead of doing laundry and still fantasizes about starting a band.
Maybe I’ve been single for so long that the idea of committing to another person is what scares me even more. What really frightens me is that maybe I’ll lose my independence and the identity I’ve cultivated while learning about myself as a single person. I don’t want to have to calm my quirks for someone else, because I fiercely love those parts of myself.
For anyone else in this position, maybe acknowledging that is the first step to understanding where to go from here. After all, calling out those fears may mean we’re finally ready to address them. As for today, do I see myself dating women in the future? No, I don’t. Did I have fun? Why, yes, I did.
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