Dating Diary - One Man’s Story Part 2

Our single guy in the city shares his latest adventures—including one very awkward moment.

By Matt S.

n this second installment of Happen’s new dating diary, single New Yorker Matt S. is confronted with an awkward situation: A girl he made out with two weeks ago has sent him an email asking “So… what’s up with us?” Should he tell her the harsh truth — that he’s not interested — or pull a disappearing act and hope she takes the hint? Read on for his decision.

Monday, 10 a.m.
Ugh. What should I do about Laura’s “We need to talk” email? Am dreading writing a response. Last time we met up was two weeks ago; we were on a third date. After dinner I’d offered to show her the view from the roof of my apartment building (my foolproof
Nothing keeps me from wallowing in rejection like a few more dates.
get-her-up-to-my-place ploy) and we made out before she went home. Yes, I enjoyed spending time with her (and kissing her), but just wasn’t feeling this could lead to a relationship. That didn’t mean I wasn’t hoping it would lead to bed (I’m a guy, after all). I guess I’d fooled myself into thinking she, too, would be fine with a purely physical relationship. But obviously, her email — which said, in a nutshell, “Where’d you disappear to, don’t you like me?” — indicated otherwise. Ouch.

Guilt was now churning my stomach like bad Chinese takeout. I weighed whether I could get away with not replying to her email at all and hoping she’d take a hint, but then realized we had way too many friends in common (we’d met at a mutual pal’s party). Next thing I know, I’d be blackballed in the entire tri-state area. So I wrote a genuine, apologetic response saying she was a great girl but that all I could offer her is my friendship. Then I hit “send” and prayed it wouldn’t make her feel too bad.

Then I sent one last email to Sarah—the girl I really like but haven’t seen in almost a month. It’s ironic: The email I wrote to Sarah was strikingly similar to the one Laura had sent me. Why do I always want the girls who don’t want me and push away the ones who do? Am I really into Sarah, or just into the chase? And if Laura had been ignoring me, instead of vice versa, wouldn’t I be more into her?

Jeez, I hope I meet someone soon who helps me transcend all this doubt about whether I’m really feeling what I think I feel or not. Isn’t that lovin’ feeling supposed to be obvious?

Monday 4 p.m.
Phew! Laura wrote back. She says she’d be happy to be friends. Not that I really need another platonic female friend
Nothing keeps me from wallowing in rejection like a few more dates.
to add to the growing hoard of them I have already. In fact, all told, there are 52 women entered in my phone book (compared to 20 guys), and all but four of them are platonic friends. That said, Laura is one of the few people I’ve played Scrabble with who can beat me, and I respect a girl who has a way with words.

Of course, the girl I do want, Sarah, hasn’t responded. What did I do wrong? I went all out on our last date—inviting her to my apartment, cooking dinner for her, sending her home with leftovers and even homemade cookies. I’ve reread and rereread our emails; nothing jumps out as an obvious turnoff. At this point, honestly, I don’t even care if I see her again. The only reason I want her to return my email is to know why she doesn’t like me.

I need an ego boost, bad. And nothing keeps me from wallowing in rejection like a few more dates. Time to get on Match, follow up on old leads, and drum up some prospects for the weekend.

Friday, 8 p.m.
I’ve scheduled three dates on Saturday—that’s definitely a record. Granted, marathon dating days can be a bit stressful; some might even call it shallow. But in my experience, dating truly is a numbers game: I’d say there’s about a one-in-three chance I’ll like a girl and she’ll like me. Schedule three dates, and odds are in my favor that one will have some decent potential. It also makes each individual meet-and-greet easier. Since I’m less likely to obsess about any one girl, there’s less pressure, and the confidence I gain having easy banter with each snowballs over the course of the day. I feel pretty studly by the end. And that’s good, because it’s Date #3 that I really want to impress.

Date #3 is with Faith. Cute, curly dark hair and a very voluptuous figure. We met up once more than a year ago at a bar, and — thanks to my bartender-friend who kept plying us with free drinks — hit it off. Really hit it off. As in, “making out like horny high-schoolers in front of everyone” hit it off. After that, Faith and I flirted over email and talked about meeting up, but days turned into weeks, weeks into months, then — as what tends to happen to pretty girls — she got a boyfriend. I kicked myself for days afterwards. Had I been more diligent in pursuing her, might I have become that guy?

Recently, though, she’s become single… and agreed to meet up with me. Maybe this is finally my shot at something big…

Matt S. is a 30-year-old magazine writer and editor looking to meet The One among the 1.95 million single women in New York City. His search will be chronicled on Happen every two weeks.

Click here to read the previous installment of this dating diary. Click here to read the next installment. Click here to read our gal writer's diary.

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