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Dating Diary - One Man’s Story Part 3


Does having three dates in one day up a guy’s odds of success? Our writer is about to find out—and make one very embarrassing phone call.

By Matt S.

n this third installment of Happen’s new dating diaries, single New Yorker Matt S. schedules three dates for one Saturday. His thinking: at least one of them will pan out as a success. Will his “dating is a numbers game” gambit yield a love connection? Read on to find out.

Saturday, 11 a.m.
All right! It’s three-date Saturday! Sure it’s a bit excessive, but I’m a firm believer that there’s power in numbers—how can I not hit it off with at least one of these girls? Plus, stacking meet-ups makes each one progressively easier as I get my mojo rolling with each date, and I need to be at my most confident for my third. It’s with Faith, the girl I
With two dates under my belt, I’m feeling 80% Alpha Male for date number three.
really want to impress. Faith and I had made out once in a bar a year ago, but she got snatched up by some other guy before I could really make my move. Now, however, she’s available. While I’d never admit it to her, Faith has entered my mind all too often in the past year. Has she been thinking about me? Time to go find out…

Saturday, 6 p.m.
Two dates down, one to go. My first, at 2 p.m., was with Sam, a self-described “cheeky” Brit I met online. As is too often the case, I knew as soon as I laid eyes on her that this wouldn’t work. She’s attractive, but she appeared nervous and even a little wary. Confidence and optimism are so crucial for a first meeting. Without ’em, the date becomes a humdrum mini-interview focusing on what we do for work, where we grew up, and how many siblings we have (“Freelance writer,” “North Carolina,” and “three,” by the way). And that’s precisely how we spent an hour together drinking coffee at Starbucks. Unfortunately, she exaggerated her “cheekiness”—my dry sense of humor is more British than hers. We parted amicably, with me saying, “Talk to you later!”—a little white lie that avoids the awkwardness of an on-the-spot rejection. Everyone involved generally knows it’s code for “goodbye forever!”

My second date was at 4 p.m. with Alina, a girl I met online whose headline — a lyric from a relatively obscure Beatles song — caught my eye. We’d arranged to meet for coffee (although I was already very caffeinated due to my café latte with Sam). Alina, thank god, was the yin to Sam’s yang: all positive vibes. We talked easily about everything, even dating—normally an awkward topic but not with someone as peppy as Alina. Unfortunately, just as things were getting good, I had to leave for my third date, kissing her on the cheek and saying “Let’s do this again soon!” Dang. Who knew what
I’m feeling 80% Alpha Male for date number three.
could have happened if I’d allotted more time with Alina?

With two dates under my belt, I’m feeling 80% Alpha Male for date number three. And that’s the perfect mindset to be in to meet Faith. And I have a great time planned for us: an outdoor salsa lesson followed by hours of live music and dancing. Is another long-overdue makeout session in store for us?

Saturday, 11 p.m.
Wow, what a difference a year can make. Faith looked as cute as I remembered her (a miracle given how plastered we were when we met), but her attitude seemed light years less jovial. Salsa, it turned out, just wasn’t her thing, so after a few rounds on the dance floor, we moved to plan B: an upscale bar where we shared a few appetizers and talked. But even then, she was a bit of a downer. Granted, I tried my best to be interested in her soliloquies about her recent troubles — she’d been fired from her job, her friends were annoying her with snide comments, and her landlord had threatened to evict her when she’d missed rent payments — but as I watched her mouth move, my mind had already wandered to the DVD I’d rented in case tonight was a bust. Chalking up our year-ago makeout session to a booze-fueled fluke, I walked her to her cab, kissed her goodnight on the cheek, and fled home to watch Chunking Express. Thank god for Netflix.

Sunday, 12:30 p.m.
Man, dating is exhausting. But it looks like my three-dates-in-one-day ploy may have paid off: Two were duds, but Alina is totally up my alley. Should I call her? Maybe better to wait one more day. To distract myself, I decided to call another prospect, Allison—a 34-year-old high-school teacher I met on Match.com. She’d emailed me her phone number, so I decided it was time to take the plunge and call. Only problem is, I got her voicemail, which forced me to leave a message: “Hey, this is Matt! We’ve been emailing a bit, and you sent me your number, so I thought I’d call. So… call me back!”

Given this was the first time she’d hear my voice, I started wondering: Did that sound as desperate as I feel right now? For better or for worse, her voicemail offered me the option of listening to my message. So I did. And as I’d feared, it definitely sounded too eager beaver, at least to my ears. So I pressed the option to re-record my message. “Hey, it’s Matt. Ummm…”

Crap. Scratch that. I made one more attempt: “Hi! This is… Matt. I’m just calling to say hey. Gimme a shout back. Later!”

God that was goofy. The “later,” in particular, sounded shrill. And sad. And (admit it Matt) desperate. Still, I can’t continue recording and re-recording all day here. And what if technology fails me and she receives all three messages in a row? Admitting defeat, I hit send. I’m done trying to make a good impression on women. Now it’s her turn.


Matt 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 for the next installment.

Click here to read our gal writer’s diary.


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