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Dating Diary - One Man’s Story Part 5


Our writer meets a great new girl at a party…but has she slipped away already? And so he sets off to do some detective work.

By Matt S.

n this installment of Happen’s dating diary, single New Yorker Matt S. clinches a second date with Allison—and gets intrigued by a new prospect. A female friend, however, warns him that his latest crush comes with some strings attached. Read on to find out what they are—and what he decides to do about it.

Thursday, 2:30 p.m.
Finally got in touch with Allison and have our second date planned next week. We’re going to the Museum of Modern Art (her idea). I love museum dates: There are plenty of things to chat about, and there’s something hot about a girl who’s into art. Just wish her schedule
Maybe this is why I’m still single: Every time I meet someone I like, I bungle it.
wasn’t so busy: I was really angling for an evening together in the hopes it would lead to a night together…

Going to a party this Friday to send off my gal pal, Sheila, who’s leaving for Italy. She guarantees that cute co-workers will be in attendance. Am looking forward to seeing if I hit it off with one of them.

Friday, 2:30 a.m.
Just back from my friend Sheila’s going-away party. Indeed, the co-workers were cute, and I immediately approached a group and launched into a quirky story that I hoped would capture their attention. I told them about how recently a girl I knew in college had tracked me down out of the blue. Did they think it was odd that she’d contacted me? My hope was that the anecdote would subtly demonstrate my allure—that I’m so intriguing that a “girl I knew in college” (without spelling out how closely we knew each other, leaving it to their imaginations) would try to find me. The girls took the bait immediately and began offering suggestions for dealing with it.

I became a bit smitten with a cute, funny brunette who showed off fantastic dimples when she smiled. But given I’d been introduced to her and six other girls at once, I instantly had forgotten her name. Was it Tara? Carrie? Lauren? Why can’t I pay better attention when I meet people for the first time?! I tried to make do as best I could by not calling her anything, but I knew I was putting myself at a disadvantage—nothing is sweeter to the ears than the sound of someone else saying your name.

Maybe it’s a cheesy guy thing, but I’d intended to excuse myself after chatting for about ten minutes. Doing this gives the girl the impression I am in demand — that I simply must share myself with other people at the party — and leaves her wanting more (since we all want what we can’t have). Only problem was, she and her friends left me before I could leave them: They were off to another party.

Not sure what to do, I called out, “Nice meeting you!” to all of them as they made their way to the door. Stupid! Cowardly! Why didn’t I ask for her number? And even if I had, how would I get in touch with her if I didn’t even know her name? Maybe this is why I’m
Every time I meet someone I like, my mind goes blank.
still single: Every time I meet someone I like, my mind goes blank, and I bungle it.

But not all was lost. My friend Sheila obviously knows her, so I’d just hit her up for the girl’s number. So I sidled up to my friend and said “So your friend is cute! You know, the one with the dimples… What’s her name?”

“You mean Rachel?” Sheila asked. Great—another Rachel. My ex-girlfriend seems to share her name with half the women in New York City. No matter. But when I asked Sheila what she was like, things went from bad to worse. “She’s kind of high-maintenance,” Sheila said.

Uh-oh. Did that mean she demands low-fat soy in her cappuccino, and will send me on errands to pick up her dry cleaning? “High maintenance how?” I asked.

“Oh, I don’t know,” Sheila said. “She’s just seems kind of stuck-up.”

Hmm… I trust my friend, but Rachel didn’t seem snotty at all—at least to me. Maybe she just doesn’t get along well with girls; some women are more comfortable around guys. Or maybe Sheila had ulterior motives. She and I had always been platonic pals, but still, her lack of enthusiasm for Rachel seemed unwarranted. Was Sheila being a friend and warning me to steer clear, or was she letting a bit of jealousy get in the way of me having a good time with this girl?

I considered pressing Sheila for her contact info, but decided to let it go for now. But ironically, her words of warning had the opposite of their intended effect: Rachel was forbidden fruit. And I know this sounds awful, but hearing that a girl is “not nice” or even “stuck-up” is a bit of a turn-on: She was nice to me; if she’s a snob, then I’m somehow good enough for her to talk to! OK, I need to reign in my analysis of why I’m interested in this girl. Point is, I want to see her again.

Only how should I get in touch if I don’t know anything about her other than her first name? Suddenly, the answer comes to me….


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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