JUST WINGING IT DATE #3: IT’S GOING DOWN, I’M YELLING TINDER

Cosmopolitan.com

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

JUST WINGING IT POST #2: THE OPPOSITE END OF THE SPECTRUM

Nerve.com

Nerve.com

Sometimes we’re shown the left limit and then the right limit, just so that when we find the sweet spot in the middle, we’ll know it. Such is the case with this next date – a far cry from F Train Bobby, for sure.

The set up: Met through mutual friends at a happy hour in midtown. Eventually met for drinks in my neighborhood on a Monday night.

The guy: After our initial meeting – in which we spoke for only about 15 minutes – this next guy, who we’ll call Serious Steve, emailed our mutual friend. He offered an editorial recommendation for me and told her to pass it along, so I emailed him back a thank you. So began our back and forth.

For the record, before I even met this guy I’d seen him do two very considerate things: bring a present to his female friend for her birthday (seriously, what hetero man does that without his wife or girlfriend orchestrating it?), and email an unsolicited helpful career suggestion. So I went into this date with high hopes, to say the least.

Age: 38. Ironic since the date I’d had right before this could’ve been his son.

Hometown: Can’t remember, but we spent most of our time talking about a city in which we both used to live.

Occupation: Not finance. Something with product design, software, or that generally requires that he be exceptionally smart. Which he was, in an unpretentious way.

Height: Enough inches taller than me that it was a non-issue.

The date: We met for after work drinks at my neighborhood pub, and had a light dinner. He was dressed nicely, well-mannered (you know how much this matters to Miss Wingman) and gentlemanly. He picked up the bill without hesitation.

Not long into chatting, I realized how reserved this guy was. Not just because he’s Serious Steve, but because there was something so measured about his demeanor. These are hardly bad qualities – the last person I dated was similarly methodical – but I couldn’t help but think how much my personality seemed to bowl his personality over. He didn’t make me laugh, and I’m not sure I got more than a smile out of him either.

We chatted for about two hours, during which time we had several things in common, but there was no discernible spark. And I really, really wanted there to be. I knew how great he was, but I couldn’t avoid the voice in the back of my head that said, “This isn’t your guy.”

When we eventually parted ways, I had every intention of giving him a second chance, just to confirm my suspicion. But as it turns out, I wasn’t free the next time he emailed, and after the holidays he didn’t follow up and I didn’t revisit it. For the best, I suppose. Perhaps he sensed the disconnect.

Postgame analysis: Now before you all cry wolf, or rather “See! Nice guys DO finish last!” hear me out. Miss Wingman’s dating history has always been in direct contrast to that stigma. I only ever date respectable, mature, sweet guys, and I’ve been blessed with a steady stream of anti-jerks (well, for the most part, at least.)

So my lack of chemistry with Serious Steve had nothing to do with him being too nice, or boring, or whatever other adjective you’ll hang this on. It has to do with a general feeling that there’s a difference between being an adult, and being too grown up. Just like there’s a difference between being immature, and being young at heart.

I know myself, and I need someone who strikes a balance between having his act together, and not taking himself so seriously that he can’t dance to Kesha at a bar with my friends and I (which is all I feel like doing these days) and take a Fireball shot…or three.

It’s nice to balance each other out, but sometimes this extrovert finds that her energy and/or sarcasm overwhelms my counterparts. And when it does, that’s my cue to put my hand up and say, “Check, please.”

Figuratively, but sometimes literally, too.

The takeaway: While I have an enormously high opinion of this dude (seriously, single ladies, if anyone wanted his number I’d endorse him), I just know that he and I didn’t par. It goes to show that, much like the last relationship I had, even though it looks good on paper and there’s mutual admiration, there has to be enough passion on both sides to keep it afloat.

Final Score: 4 Web out of 5. Like I said, he’d be an outstanding catch for some woman – the right woman – but I’m just going on instinct that the lucky lady isn’t me.

Next up, Wingman faithful, my first ever Tinder date. And a chance to choose which of my Match.com suitors (please don’t let it be the 41-year-old from Forest Hills who can’t spell) will get a shot at the title. Remember to keep it right here for more of Miss Wingman’s “Where Are All The Good Men In NYC?” Experiment, get your friends in on it if you’re so inclined, and until then, as always, I’ll be just winging it.THAT’S WHAT SHE SAID

Facebook Twitter

JUST WINGING IT POST #1: F TRAIN DUDE

F train bobby

You know you’re keeping an open dating mind when you meet a guy on the subway.

I know, I know. Who does that? I’ve lived in NYC forever and never so much as made eye contact on the train, let alone talked to someone on the platform. But this past encounter (Miss Wingman has to backdate some of these adventures) left me challenging my previously-held belief that you can’t pick someone up on the subway.

So without further ado, here’s how it all went down.

The scene: F train platform on a Friday night, post-friend’s birthday cocktails in midtown.

The guy: *Bobby (*Obviously his name’s not really “Bobby.” But I do enjoy that this makes him sound like he should be one of Jan’s crushes on “The Brady Bunch.”)

Age: 24. Yup, you read that right. I could’ve practically babysat for him. Hometown: Somewhere in Massachusetts.

Vocation: Something finance-y for a well-known company I won’t disclose, but he was dressed well and appeared normal and clean cut.

Height: At least 4″ taller than me. And yes, that usually matters to us (sorry boys.)

The approach: Thanks to a very unusual subway platform performer who was playing music seemingly without an instrument (long story), we both stared at her in confusion for a minute, made eye contact and started to laugh. This broke the ice enough, small talk ensued, and it came out that he was just at the gym. Due to our location, I asked if he went to New York Athletic Club. He said yes and with that common ground (my grandfather was a fixture there once upon a time), we ended up chatting the whole ride downtown.

When we eventually got off at the same stop, he hit me with, “We should get a drink sometime.”

I’m pretty sure I laughed in his face and said something like, “Did you seriously just ask me out on the F train?” He replied with, “I’m going to meet friends for a birthday, so if you met me 15 minutes from now I’d be ‘The Guy You Met At The Bar’ and not ‘The Guy Who Picked You Up On The F Train.’”

He had a point, and that – coupled with the fact that he seemed normal and harmless – clinched it. I gave him my card.

The date: Fast forward to him being surprisingly charming over text message, so we agreed to meet in the East Village for drinks on a Friday. At this point, I knew he was 24 (yes, you definitely Google dudes you meet on the F train) but he didn’t realize how much older I was than him. When I broke the news, he said I was the only one hung up on it – he didn’t think I looked or acted older. Game on, apparently.

(*Miss Wingman note: While that’s sweet, and I’m often told how young I look, no one wants to be the novelty story you tell your friends about the time you took down a cougar. This was never going to end well…)

Drinks turned into a late dinner, and though I never had any intention of seriously dating someone who graduated from college in 2012, at this point he was winning me over.

Flag on the play: All this changed at the end of the evening when it became apparent to him that he wasn’t going to close the deal (again – my parents read this, so no further detail) and he showed his true age – by pouting. Hardcore. And then it got really, really awkward.

Postgame analysis: To his credit, he followed up with some casual banter text messages in the days following, presumably so he wouldn’t look like a dick. I haven’t spoken to him since, and although he did impress me by being surprisingly mature for MOST of the night, the end of it was telltale. LET THIS BE A LESSON FOR ALL MEN: if you’re going to put in the work and the time, don’t throw it all away by showing your was-just-trying-to-get-laid cards in the final stretch. We assume that anyway, but there’s no need to tip your hand.

The takeaway: Don’t date boys who were born the year you were old enough to get your own phone line. Also, shared humorous/awkward circumstances (Tall Dave, anyone?) make for the perfect introduction. It’s an easy in.

Final score: 3 out of 5 Web‘s. Normally, I’d give a dude a score of 1, but F Train Bobby deserves serious credit for pulling digits on public transportation.

So that’s it for the inaugural post of Miss Wingman’s Good Man Experiment, aka “Where are all the good men in NYC?” aka sweet-Jesus-what-have-I-gotten-myself-into? Obviously these initial ones will be on rewind, but stay tuned for upcoming chances to roll up your sleeves and get involved. Until then, as usual, I’ll be just winging it.THAT’S WHAT SHE SAID

Facebook Twitter