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Dating Diary - One Man’s Story Part 4


Will our writer work up the courage to kiss a woman he feels could be The One? Read on to find out. Plus: The phone faux pas he’ll never commit twice.

By Matt S.

n this fourth installment of Happen’s dating diary, single New Yorker Matt S. finds out whether the voicemail message he recorded, re-recorded, and re-re-recorded to a woman named Allison made a good enough impression to get him a date… or did she receive all three of his bungled attempts to say “hi”? The answer’s ahead.

Monday, 10:15 p.m.
Allison called me back. And she sounded
The beautiful scenery screamed make a move already! but I just couldn’t do it.
friendly enough that I have to assume her voicemail hadn’t malfunctioned and given her all three of my messages, but had recorded over my failed attempts and left her with just my last greeting. Phew! But that’s definitely the last time I try listening to the message I leave on someone’s voicemail. It’s just too tempting to re-record it to perfection. And honestly, is a stray “Um” really going to convince a woman no to see me? It’s rough out there, but not that rough.

Allison and I chatted for 20 minutes about her work—not her teaching job, but her side work (she's a playwright and is preparing for a stage production that's opening for two nights next week). Then we made plans to meet for Wednesday after work. Score!

Wednesday 6:45 p.m.
I like Allison! The conversation flowed over iced coffee. She was, however, a bit preoccupied with her one-act play and even took phone calls regarding last-minute planning while I sat and eavesdropped. Normally, I'd find chatting on a cell in the middle of a date a huge turn-off, but she was super-apologetic and had warned me ahead of time that she was expecting interruptions. Plus she's cute—and cute can go a long way to make up for any faux pas. After finishing our drinks, we strolled around the neighborhood and to the Brooklyn Bridge promenade. The beautiful scenery screamed, Just make a move already! but I just couldn’t do it. Why, why, why? In my defense, it was the afternoon, not evening. Getting together during the day can ease some of the pressure of a first meeting, but it also dampens the sexual tension. A first kiss can't happen in broad daylight, can it? If only I'd suggested we meet for happy hour instead. Dang.

Even so, the way Allison smiled at me at various points made my mouth dry with anticipation. Did she want me to kiss her? But what if I were completely misreading the signals? There’s nothing more awkward than kissing a girl who doesn’t want to be kissed, and it’s always up to us guys to figure out what our dates really want. It’s just not fair.

Finally, Allison said she had to get back home to do more work on her play, and we parted ways with a hug. Lame. Oh well, I’ll just have to make sure our next date is more kiss-inducing. That is, if we have a next date.

So when should I call her? Will calling within 24 hours seem too eager, or will she write me off if I wait any longer? For a female point of view, I called my friend Erin. But I knew what she'd advise me to do: “Call her, of course!” she said. Easy for her to say,
Normally, I'd find that a turn-off, but she was cute—and that makes up for any faux pas.
since she never has to do the calling. And in my experience, girls always say guys should call the next day, but then turn around and think those who do call are overeager. All in all, it’s impossible to get it just right.

Thursday 12:15 a.m.
Instead of calling Allison today, I emailed her. Yes, I admit, it’s a bit of a copout. But the truth is, like most men, I'm generally not a big phone talker, and I prefer to use my cell purely to make plans, and use email for more in-depth discussions. So I wrote her a light “Great meeting you, hope your play preparation is going well” and hit send.

Wednesday 8:30 p.m.
Still no email from Allison. Am I missing something? I’d even caved and left her a voicemail over the weekend (and this time, I stuck with my initial recording. That’s definitely an improvement over last time). But now it got me thinking: Maybe Allison is miffed I didn’t call her after our date. Or maybe she’s busy with her play. Or maybe she’s just not that into me. Anyway, it’s time to find out: by calling her one last time. Here I go.


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 in this series. Click here to read the next installment in this series. Click here to read our gal writer's diary.


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