You’re not officially involved in the New York dating scene until you’ve sacrificed your profile photo (and, in some cases, your dignity) at the altar of a GPS-based dating app. But Miss Wingman finally pulled the rip cord, and recently went on her very first Tinder date. This is what happened.

The set up: Mutual right-swiping, Tinder style.

The guy: A sensitive ponytail man-type, only without the ponytail. Clad in a cardigan and rocking at least a 3-day shave stubble, we’ll call this dude Soft-spoken Sean.

In what can only be called a supremely small metropolitan world, when Soft-spoken Sean initially chatted me up on Tinder, the first thing he said was, “Do you have a friend named *Marni?” (*yeah, that’s not her name either.) I do, in fact, have a friend by that name, and he proceeded to tell me that he’d only ever met one other person with my first name, and that person was at his then-girlfriend’s birthday party nine years ago. Yes, 9.

He told me that at the time he’d thought I was cute, and when I popped up in the Tinder-sphere, he had a hunch it was the same person. I didn’t know whether I should be very flattered that this relative stranger remembered me, or mildly creeped out. But, after texting with her to confirm that he was normal, we agreed to meet for coffee in Brooklyn on a Saturday afternoon.

Age: 33

Hometown: I suck, but I completely forgot what he said. I’m sure it was something in the tri-state area though.

Occupation: Film and television producer. Er, Production Assistant? AP? Fuck if I know. Dude had left a job in finance in his late 20′s to get his masters at a prestigious NYC university specializing in journalism, and since he’d only been in the production game a few years, I assume his job was support staff. But props to him for making the jump. Miss Wingman’s a big proponent of finding your passion.

Height: Tall – at least 6 feet. Arguably the most manly thing about him, in fact.

The date: It doesn’t get more placid than a coffee shop in DUMBO in the middle of the day, with someone to whom you already have overlapping social connections. So needless to say, I was expecting things to be pretty low key. Just not quite like this…

The date was really sedate. Like, they couldn’t have been more cozy or platonic if he was curled up on a sofa with a cup of tea and a cat in his lap, sedate. And speaking of tea, that’s what he ordered. Not joking! And no, he’s not British.

Um, yeah. I think you can probably see where this is going already.

Fahhhk, I can’t say enough good things about this guy, either, but once again there was no spark on my end. Maybe it was because Soft-spoken Sean and I spent so much time talking about our production backgrounds and being caffeine-driven film & television gurus who work until 2am and never have health insurance, but it felt like he was a friend. Or maybe it was because he just didn’t seem like a guy’s guy.

In any event, something was missing (his masculinity, perhaps?) and I felt like I was the dude at the table, not him. I can’t emphasize enough how sweet, intelligent and pleasant he was, but it seemed more like an afternoon you’d have with your aunt over a cup of camomile than a Tinder date. Where was the flirting? The “You wanna get out of here”‘s? Much like my coffee, I’m afraid, it was all a little too vanilla.

Postgame analysis: Soft-spoken Sean has a lot – and I mean alot – of good qualities…for some other girl. Some vegan, Rachel Maddow-watching, cat-owning Williamsburg girl. Just not this chick.

The takeaway: Alas, I need more of “Smartass Sam” than a Soft-spoken Sean.

Final score:Webout of 5. I enjoyed talking to him, and I liked him immensely as a person. I’d actually be friends with this guy, and I don’t mean that in the bullshit, disingenuous way that most people do. Still, getting Friend Zone’d is the kiss of death. I suck, I know.

Next up Miss Wingman’s sorting through a mountain of Match emails, though the front runner seems to be a 39-year-old Oxford grad who moved to Brooklyn after several years abroad and, if his profile photos don’t lie, enjoys tennis, having good hair, and fairisle sweaters. What do you think, Wingman faithful, should I give it a go?

Weigh in on what you’ve read so far, boys and girls, and in the meantime, as usual, I’ll be just winging it.THAT’S WHAT SHE SAID

Facebook Twitter


Maybe it’s because it’s Friday the 13th, therefore the dating horror stories are especially freaky. Or, maybe it’s because my readership is older than I thought. But either way, today’s ODHSOTW is the first one of it’s kind, and I’ve never heard anything like this before. Thank God.

And for what it’s worth, I’ve heard a lot since starting this feature. We’ve had run ins with exes, people double booking, couch pee-ers (not a real word, fine), people who’ve forgotten they slept together, and now this. If I were you people, I’d say it’s getting harder and harder to justify that Match.com account right about now, but who am I to judge…

This week our short-but-sweet tale comes from James in New Jersey. His story may just beat out the brother and sister who were paired up by a dating site. And by “may just,” I mean “definitely.” Enjoy.

Sarah, the accidental double date: “I guess I should’ve known something was up when most of this girl’s online dating profile pictures were head shots. But she was pretty, and we shared a lot of the same interests. So, when we agreed to meet at a bar in her town, I was still pretty optimistic. She said to meet at 8pm, but when I got to the place I looked around and didn’t see her. It wasn’t all that crowded (it was a Wednesday), but I scanned the bar and did a mental inventory of what I saw: college kids, old couple waiting for a table, pregnant chick, guys watching the basketball game. No date.

If you were surprised that I said a pregnant chick was at the bar (she was sipping water, in case you were wondering), you probably wouldn’t be as surprised as I was when that pregnant chick turned around to face me and it was HER. I repeat: the girl I was there to meet was quite obviously pregnant. As she smiled and walked over to me I actually said out loud to myself, ‘You’ve got to be kidding me.’

I don’t remember much between noticing her belly – not huge, maybe half term, but still pregnant – and sitting down at a table for small talk. I think we exchanged pleasantries, sipped some water and told our waiter we needed a minute. A minute? I needed a bottle of whiskey at that point.

We managed to order and chat about my job, the weather and how her friend had recommended the restaurant. But I couldn’t avoid the elephant in the room any longer, and she could probably tell because thankfully she came to my rescue. “So you’ve probably noticed that I’m pregnant…” she said.

I actually choked on my food, like you see people do on TV. “Um…yeah,” I said tentatively. I told her that I didn’t want to say anything, because guys know that even if a woman’s about to give birth, you don’t ask her if she’s pregnant for fear of being wrong and offending the girl.

She said no, it’s OK, she was definitely “with child,” and that she’d decided to do artificial insemination after she realized that she wasn’t getting any younger. She told me that she knew that by the time she found a man, got married and started a family, it’d be at least four or five years and that she was already well into her thirties. She didn’t want to wait around any longer.

I smiled, nodded, and politely explained that while she was great, I just didn’t sign up for that. I felt like a jerk (ironic, she should’ve been the one to feel bad for not revealing this sooner), but she said that she wasn’t upset, I’d stuck around even longer than most people she met on dates. I couldn’t wait to get out of there. Thanks, nice to meet you, good luck with your labor. Catch you on the flip side.

I know people always say women are crazy, but this chick takes the cake. Women of the world: if you’re going to multitask, wait until after you’ve had the kid to get into the dating scene. Ambushing a guy with a pregnancy before you’re even dating is just bad form.”

James: Sweet Mother. You just hit a walk-off homer, I can’t even touch that. I know I’ve said this before, but this time I really, really mean it. Game over, you win. –MW.THAT’S WHAT SHE SAID

Have a dating horror story to add? Drop me an email, misswingman@gmail.com. And remember, the only upside to a bad date is if you use it for our selfish amusement.

Facebook Twitter