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Dating Diary - One Man’s Story Part 8


Will a wingman help him score some numbers? Read on to find out. Plus: one thing women would be very surprised to find out men own.

By Matt S.

n this installment of Happen’s dating diary, single New Yorker Matt S. takes his mission to find The One to the streets, enlisting his buddy Eric to act as his wingman for an evening of bar-hopping. Will his friend help him succeed? Read on to find out.

Saturday, 9:30 a.m.
Last night I did something I rarely do: go out with the express purpose of hitting on women. Generally I go to bars to relax with my friends, not to get numbers. To me, there’s something slimy about guys who goes out to mack—the cheesy pickup lines, the
She has a nose ring—which, in some strange way, bodes well in my mind.
premeditated plans of attack, the way they see dating as a game and women as their opponents. Why would any woman fall for that ruse when there are sweet, sensitive souls like me out there?

As I got dressed for our evening out, I was pleased to discover that my recent workouts were paying off: My “skinny jeans” (yes, guys have these, too) were becoming more and more comfortable. All in all, I felt pretty hopeful as I left my apartment to meet up with my designated wingman for the evening, a buddy named Eric.

We started off at a club with hip-hop music and breakdancing. There were a few cute women, but when I approached them, conversations fizzled quickly in the din. I asked one girl, for instance, whether the coordinated moves I was seeing on the dance floor were part of a routine, perhaps for a competition? OK, so it’s not a great pickup line, but in my experience it doesn’t really matter what you say—if a girl likes what she sees, she’ll stick around and make the conversation work. Unfortunately, this girl responded with a yelled, “Huh?” I tried again, but she gave me no real indication of interest, much less a smile. So I moved on to what I thought would be an easier target, a woman who was a little on the mousy side. I said “hey” and asked if she knew how to break dance. When she said she didn’t, I demonstrated my three-second robot and told her I could teach her the pop-and-lock. She laughed, but soon excused herself… and never came back. Ouch. Apparently, even the mousy ones had better things to do than talk to me.

That night, Eric and I approached about fifteen girls—and we secured zero phone numbers. Back at home, I drifted off to sleep worried that I was getting too old to be meeting girls at dance clubs—but still too young to be jaded enough avoid them. What’s a guy in my situation to do?

Saturday, 10 p.m.
Just back from a meeting with my friend Wendy. Even though she’s off-limits dating-wise — she’s married — I really enjoy talking her. I think this has a lot to do with her seeming to understand how difficult “meeting someone” can be and yet is herself living proof
I always saw the grass as being greener on the other side.
that the search is worth the effort. We discussed the paradox of choice with regards to dating in New York—how the huge number of single women (and men) in the city makes it harder rather than easier to find someone, since there could be a “better” match just around the corner. This is a particularly troubling notion for me, having been accused by not one but two exes that I was incapable of making a commitment because I always saw the grass as being greener on the other side. Thinking about it freaks me out; talking about it with Wendy was reassuring.

“You’re young!” she told me. “If I were you, I’d meet as many different people as I could. You never know what kind of person you’re going to fall in love with.” In addition to offering this comforting insight, Wendy must have called me “cute” or “adorable” about a dozen times. Why aren’t I meeting women like her—but, you know, single? Or is it the fact that she’s taken why I can relax and be myself?

Whatever the case, my mood was much improved by our conversation—she made me remember that there was plenty of reason to be hopeful. When I got back home, I decided to reply to some Match.com prospects with a new outlook. One girl in particular seems promising: a cute, athletic 24-year-old. She has a nose ring—which, in some strange way, bodes well in my mind. Plus, her profile’s headline bodes really well: “I have a bod made for sin.” And from the very suggestive emails she and I have exchanged, it seems like she’s very open to committing some transgressions with me. Or is this girl too good to be true? Time to ask her on a date and find out.


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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