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Dating Diary - One Man’s Story Part 6


Our writer ponders the allure of “high-maintenance” women—and learns the hard way how not to ask a girl out (hey, live and learn…)

By Matt S.

n this sixth installment of Happen’s dating diary, single New Yorker Matt S. seeks out the contact info for Rachel, a promising — albeit “high-maintenance” — prospect he met at a friend’s party. Will his detective work score him her digits so he can ask her out? And if so, will she say yes? The answer’s ahead.

Sunday, 5:45 p.m.
OK, my pal Sheila has duly warned me: Rachel — the girl I met at a party Friday and hit it
I’ve been warned: Rachel was “high-maintenance.” Is that so bad?
off with — was “high-maintenance.” I generally trust Sheila’s judgment, but I can’t simply let one friend’s opinion keep me away from a woman I like (and who also has the cutest dimples when she smiles). Besides, what’s wrong with a woman who’s a little demanding? Maybe “high-maintenance” is another way of saying she knows what she wants in life. Of course, maybe I’ll feel differently once I see Rachel’s “high-maintenance” personality in action on a date, but right now, I must confess, I’m intrigued. I want to see for myself whether she’s worth the effort.

Only one problem: How do I get in touch with Rachel given that I didn’t have the guts to ask for her phone number when we met on Friday? Luckily, Rachel works at a public relations firm where I know a couple of her co-workers. So, I shouldn’t have a problem tracking her down. And, since I’m a journalist, I have the perfect excuse to get in touch: to discuss clients she represents and how I can cover them in the various magazines I write for. Still, will that make Rachel think my intentions for getting in touch are professional rather than personal? Probably. And I guess that’s OK.

Monday, 3 p.m.
Game on! I emailed Stephanie, Rachel’s co-worker, saying how nice it was to see her at the party—and that I’d chatted with Rachel about one of her clients but forgot to ask for her business card. Could she forward me Rachel’s info? OK, so I veiled my desire to ask
I was hoping she’d be a bit more enthusiastic to hear from me.
Rachel out by couching my request in terms of a work-related matter, but I can’t very well bluntly ask one girl for another girl’s number, right? Stephanie happily passed along my message, and moments later I received an email from Rachel herself.

I probably shouldn’t be reading too much into Rachel’s two-line message to me, but I was hoping she’d be a bit more enthusiastic to hear from me. She wrote that it was “great meeting me,” but followed directly with her sales pitch for her client’s product. I wanted to see her, not a press package about a “premium spirit” (PR talk for expensive booze). Still, it’s an opening: I can arrange to meet up to discuss work stuff and, hopefully, segue into a more personal conversation. So I wrote Rachel back, suggesting we meet for lunch.

Monday, 6 p.m.
Hm… No reply from Rachel yet. Maybe she saw through my ruse. On the other hand, maybe she assumes my interest is purely professional, and that hardly makes her feel like she’s dying to see me. I hate how the pursuit of women can make me feel so passive-aggressive: My fear of outright rejection leads me to suggest “getting together” rather than asking a girl out on a regular date, or, in this case, use work as an excuse to see someone I’m attracted to. Am I really sparing myself the potential sting of rejection, or merely prolonging the pain? And by starting off on the wrong foot like this, have I doomed “us” already? Dang, my brain and stomach are already in a knot. Will Rachel get in touch already?

Wednesday, 10 a.m.
Argh! “Allison, Museum of Modern Art, 12 p.m.” says the reminder on my Sidekick II calendar. All my romantic energies have been so focused on Rachel, I totally forgot I have my second date with Allison today—a smart, hot, playwright with a passion for fine art. Am still ticked off that we’re meeting up in the middle of the day (again), which pretty much will exclude any chance of slipping into a makeout session. But at the very least, a couple hours with Allison will keep me from obsessively checking my email inbox for any sign of you know who. What’s more, Allison, unlike Rachel, seemed to express a genuine excitement to see me when we made plans. Who knows? Maybe there’s a video installation in a darkened room where Allison and I can get a little… closer. Maybe it’s time I put my neck on the line and just go for it. I’m going to psych myself up to do just that, right now. Time to get ready for my date.


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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