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Dating Diary - One Man’s Story Part 7


Will his lunch with a work colleague turn into a date date or stay strictly professional? Find out here—plus, a drastic move he makes.

By Matt S.

n this seventh installment of Happen’s dating diary, single New Yorker Matt S. awaits a response from “high-maintenance" girl Rachel to his lunch date proposal. He bides his time with a second date with Allison, a playwright he’d hit it off with a week ago. Will sparks fly with either girl? Read on for the answer.

Wednesday, 12 p.m.
My phone’s calendar function reminded me I have my second date with Allison today—lucky thing, as with all the attention
My convoluted attempt to turn a work function into a real date had failed.
I’ve devoted to obsessing over Rachel, the “high-maintenance” PR girl, that I’d nearly forgotten. Obviously, absence hasn’t made my heart grow fonder; the time that’s passed between our last (and first!) date has served to put Allison out of my mind. I want to be open-minded and give her — and “us” — another opportunity to click, but currently I’m skeptical. I mean, if I’ve already forgotten about her, how much can I be into her? Not that I put so much stock into love at first sight, but there should be something more than casual interest after a first date. We didn’t even kiss at the end of it. Granted, I blame myself or the timing (it’s hard to make the moves mid-afternoon), but if it were meant to be, it would’ve just happened, right?

Wednesday, 4 p.m.
What’s wrong with me? My date with Allison went perfectly well, but I have no inclination to see her again. We met in the museum lobby to view an exhibit on the Dada movement. I hoped we’d spend a leisurely few hours admiring the exhibit and talking about what we saw; Allison, on the other hand, seemed intent on learning about the pieces and opted for the pre-recorded audio tour—a phone-like device she kept to her ear as she moved from piece to piece. So much for conversation, I thought to myself as we ambled silently through the galleries in our separate guided-tour bubbles.

We finished our museum visit and headed to a pizzeria. At my urging, she told me a bit about her one-act play, which had been performed last week. She refused to delve into the details, but she did say it was about a failed relationship—basically, a dialogue based
Guess the lack of feeling is mutual, which is for the best.
on her own messy breakup with an ex. I imagined something akin to The Vagina Monologues and shuddered. Certainly, it would be unfair of me to judge her based on a work I hadn’t even seen, but still for me it didn’t bode well. And it certainly didn’t motivate me to go for a kiss at the end of our date.

Thursday, 12 p.m.
All right! An email from Rachel—and she’s agreed to meet me for lunch tomorrow. But does she see this as a date, or as a work-related meeting between publicist and magazine writer? Regardless, I’m looking forward to seeing her.

Nothing from Allison—not even a “thank you” for buying the exhibit tickets and lunch. Guess the lack of feeling is mutual, which is for the best: no awkward follow-up or rejections necessary. And no point in being down about it when I have a date with cutie Rachel tomorrow.

Friday, 3 p.m.
My “date” with Rachel did not go as well as I’d hoped. Sure, it had all the trappings of a date: a light meal at a hip restaurant, easy conversation about where we grew up, our families, travel experiences—the usual. That is, until she whipped out a big coffee-table book she was hoping I could cover for one the publications I write for. That’s when it hit me: She had no real interest in me. My convoluted attempt to turn a work function into a real date had failed. At least the upside to taking a PR girl out to lunch is not having to pay for the meal. I lamely protested as she put down her corporate card when the bill arrived, but quickly acquiesced when she reminded me, “This was work!”

Friday, 5 p.m.
Swapped polite emails with Rachel: I thanked her for lunch and she replied with, “My pleasure!” So much for that.

Time to retire my passive-aggressive approach to getting girls. I’m clearly languishing in first-date-only hell, failing to excite or be excited by these girls enough for us to pursue each other. What I need is to go meet girls, spend an evening going from bar to bar and hitting on just about every woman I see. And I need a — loathe as I am to even use the cliché — a wingman.

It’s Friday night, and I have no plans. I am going to shower, shave, and put on my favorite jeans and the shirt I just bought. I’ll have my friend Eric meet me at this hip after-work place we sometimes go to. My mission: to get more girls’ numbers than can fit into my phone’s address book—or else.


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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