I scored two more dates over the weekend.  I never heard back from Art Girl, so I hit up OKC with determination and didn’t stop until I had two more girls lined up.

The first date was Saturday night with TV Girl.  She was 29, worked in television production and had an offensive sense of humor on par with my own.  We wrote each other substantial messages, which was a good sign.  I asked her out on a date and we met at a bar halfway in between our towns.  She had just gotten back from having dinner in the city with her family so we didn’t meet until midnight.

I was amazed that she was up for meeting so late at night. Everyone else I know heads home by 9 or 10 PM because “I have work in the morning.”  With my friends I’m just like… you’re working the same shitty job that you had at 22, and back then we’d hang out until 4AM even though you had to be at work three hours later.  Now we have to pull out the appointment book and literally schedule time to see each other.  And once they get married and have kids… forget it.  People aren’t as much fun as they get older.

But I digress.

As I was saying, we met at the bar.  Fun fact: it was the same bar that Teacher and I went to with the other girls in our dance class last year, where I had my first beer and all that.  But that was on a Tuesday.  This time it was a Saturday and the place was a zoo.  Geez.  I could have done without the noise.  I got there two minutes after she did and I met her just inside the door.  I snaked an arm around her waist and gave her a kiss on the cheek and told her it was good to see her.  She looked different in person than in her pictures, but still cute.

She’d already gotten herself a drink, so I got one for myself and then we found a table near the back where it was somewhat quieter.  We started swapping stories but she seemed to dominate the conversation.  Very bubbly and outspoken, and slightly brash at times.  I mused that she’d probably be more interested in a guy a little edgier than myself.

The other patrons got noisier and rowdier as the night wore on, and then a fight broke out at the next table.  There was a gaggle of girls sitting there along with a couple of guys, and then another guy came along and said something to them. One of the guys at the table stood up and they were toe-to-toe and in each other faces.  I’d seen enough Worldstar Hip Hop videos to know how this was going to go down.  Sure enough, five seconds later one gave the other a shove, and it was on.  They were wrestling on top of tables and rolling around the floor, knocking chairs over and sending glasses crashing.  I grabbed TV Girl and pulled her aside as they came within three feet of us.  And of course people were pulling out their phones to film the whole thing.  It went on for a good minute until the bouncers finally arrived and pulled them apart, launching the instigator out the back door.

Shortly afterwards TV Girl said she needed a smoke, so we went out to the back patio where she lit up a cigarette.  Meanwhile the guy who started the fight was yelling on his phone in the parking lot, and then he came charging back inside a few minutes later.  This time the bouncer caught him and hurled him right back out again.  Then the police showed up shortly afterwards there was a big to-do.  TV Girl and I watched the whole show and I kept up a running commentary the entire time.  “See, who says I don’t know how to show a girl a good time?” I joked.

By the time 1:30AM rolled around we were both cold and tired, so we called it a night.  I walked her back through the bar and out the front door.  On the sidewalk I told her I had a nice time with her and wanted to see her again, and that next time we should do dinner – someplace a little quieter.  She said she was up for it.  I gave her a hug and another kiss on the cheek and we parted ways.  I didn’t feel like we really hit it off in person, compared to the spark in our online messages.  But we’ve been texting a little bit since Saturday night so we’ll see what happens.

I didn’t have high expectations for Curly Sue when we got together Sunday afternoon.  Our online conversation was rather lackluster, but she was up for a date so I figured I’d give her a chance.  You never know.  She was 28 and even cuter in person and I was quite taken with her.  I also quite taken with the crepe place I went to with Art Girl so I went back there with Curly Sue – albeit at a different location.

The date went as expected.  It started out okay, but try as I might I just could not come up with a topic that we could run with, apart from discussing her teaching career.  She barely asked me anything about myself in return, though I volunteered plenty of information.  It reminded me irresistibly of my experience with Crush.  They even looked very much alike, now that I think about it.  But it was one of those dates that just plain didn’t work.

Eventually we ran out of things to talk about.  But that didn’t mean I wasn’t interested in seeing her flat on her back in my bed, clawing at the sheets and biting down on my shoulder to muffle herself.   I was at the point where I just felt like saying, “you wanna blow this joint and come back to my place?”  In retrospect I wish I’d been ballsy enough to try that.  Instead I called it an afternoon and we went outside.  I would have gone for at least a hug but she shook my hand just as she did when she met me.  Then we parted ways.  There was no mention of seeing each other again.

However I did text her later that day to tell her she should come over some night this week to watch The Goonies (since that’s one of our favorite movies).   I wasn’t expecting a response, but she actually texted back:  “Hey thanks for the offer, but I don’t think that we’re compatible.  Good luck, I know you’ll find someone perfect for you.” Doubtful I would have gotten a different response had I asked at the end of our date, but at least I gave it a shot.

But those crepes were to die for.  Holy shit.  I was nearing climax as I ate mine.


First dates:  28
Second dates:  3
Third dates:  2
Cancellations:  5
Stood up:  2
First kisses: 1
Sexual experiences:  0.6


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.

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 had suggested the crepe place in the meantime.  And now she was saying she didn’t know?  Looked like this was headed for another dead end.

“You said you were free either day…?” she asked me.  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.  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?  Should I even?


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.

First dates:  26
Second dates:  3
Third dates:  2
Cancellations:  5
Stood up:  2
First kisses: 1
Sexual experiences:  0.6