I’m now the 31-year-old virgin and I still haven’t caught a break. But I’ve finally landed another date. Only took me a little over two months. I’m sure the holidays are partly to blame, but it’s been exceptionally difficult to get a date lately. I’ve been hitting OkCupid hard over the past few weeks, but conversation after conversation flatlines. That seems to be my main problem. I don’t seem to be saying the right things to hold anyone’s interest or taking the conversation in the right directions. Instead I seem to fall into a boring rut of discussing work/school/family and all that bullshit and then things stagnate.
I’ve gotten more responses and first messages and dates than other virgin guys my age could dream of, but I still have nothing to show for it. It frustrates me to think that there are guys literally half my age getting laid. How are they doing it? How are they pulling it off? They’re just dumb fucking teenagers, what kind of game could they possibly have? Well… more than I have, apparently.
But I managed to work some magic with Art Girl. She’s 28 and does art therapy with patients suffering from traumatic brain injuries. We exchanged a few messages, moved to texting, and then we set a date at a crepe place. I got there a few minutes before she did and mentally patted myself on the back for my choice of venue. It was very cozy and comfortable.
When she walked in shortly afterwards I stood up to greet her. I cringed inwardly a bit as I shook her hand, wondering if I should have given her a hug instead. But I just moved right on and led her to the counter. It was our first time there so we took a few minutes deciding what to get. I told her to get whatever she wanted because it was on me.
“Aw, that’s nice of you,” she said. I wrinkled my nose at that. Usually when a girl says you’re “nice,” that’s not a good sign. So I made a joke out of it.
“Yeah, I’m a nice guy… sometimes.” She laughed.
We finally placed our order and sat down. I was curious about what her job entailed, but after a couple of minutes it was clear she wasn’t interested in discussing it in detail. She confessed that after getting 400 messages asking “What’s art therapy?” the topic was beginning to wear on her. Understandable, but I joked that she’s drawing so much interest because she’s the only one on the site who isn’t a teacher, nurse, or social worker. From there we started talking about online dating and comparing our experiences – the sites we’ve tried, the messages we’ve received, the dates we’ve been on… I learned that she’s been on the site for two months and I’m only the third guy she’s gone on a date with.
I also learned that she doesn’t like or want kids either, so we were able to bond over that as well. By that point we were finished with our crepes and smoothies, so I asked her if she was up for a game of Jenga. There was an array of board games in the shop and that one was simple and fun enough. She accepted the challenge and we played three games before she called it a night. Already? We’d only been there for an hour.
“Yeah, I gotta get home and check on my dog,” she said.
I laughed. “That’s usually not a good sign…”
She laughed too. “I’m sorry, I’m just really attached to my dog and I haven’t been home all day. I was having dinner with my parents earlier.” We spent a few minutes talking about her dog and then she stood up to leave. I followed suit, with a sinking feeling that this evening did not go as well as I thought or hoped.
We walked outside. Out on the sidewalk I said, “So do you still want to check out the museum this weekend?” She turned to face me. I had the sense that if I hadn’t said anything she would have continued on towards her car unabated.
“Potentially,” she said. Potentially. Yeah, I’ve heard that before. “I have to check my book and see what I’m doing, I’m so scatterbrained I can’t remember what’s going on that weekend.”
“Okay,” I said. Meanwhile that had been my original proposal. Her schedule didn’t work out this past weekend, but she had told me she was definitely free this coming weekend. So I suggested the crepe place in the meantime. And now she was saying she didn’t know.
“You said you were free either day…?” she asked. I answered in the affirmative and she said she’d let me know, and I said I’d talk to her soon. Then we hugged and parted ways. So maybe there will be a second date, but it doesn’t exactly sound promising. I left with a depressing feeling that I may have squandered another prime opportunity. And she was so hot, too. It’s been less than 24 hours since our date – any advice as to what I should say when I contact her?
In other news, I reached out to a girl who “fell ill” at the last minute and wanted to take a rain check. Just as I did with the others who pulled the same stunt, I wished her well and told her to let me know when she was up for our date. Two weeks went by and I dropped her a line to see how she was doing and ask about rescheduling. No response, just as expected. At least four other girls deleted their profiles in the middle of our conversations. I was texting another girl but I couldn’t pin her down on a date despite coming up with a plan and a time, so I just gave up. And there’s one I’m talking to right now and we’re in the midst of setting up a date for this weekend. So we’ll see.
And finally, be sure to check out my other blog, Descent Into Dadness. I’m off to a good start and I’m already closing in on my first 1,000 views. It’s the story of my crazy Dad and his antics. You can learn about my larger universe and maybe even gain some insight to my struggle against virginity.
First dates: 26
Second dates: 3
Third dates: 2
Stood up: 2
First kisses: 1
Sexual experiences: 0.6