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




Alright, Wingman faithful, I have a confession.

Even though I’ve been writing relationship content on this site for nearly two years, I’ve typically shied away from putting my own dating specifics directly in the spotlight. Sure, I mine my life, my conversations and my friends’/readers’ dating stories for inspiration, but I never threw the shutters open to expose the sordid details of who I’m dating and how it’s all playing out. Partly to preserve the privacy of past boyfriends, and partly to avoid sabotaging my own romantic prospects. I may be brave enough to write about sex even though my parents are reading, but I’m not crazy.

But that all changes starting today. In the spirit of full disclosure, I’m in my thirties and just got out of a relationship. It’s for the best, trust me, but that doesn’t make it any easier to acclimate. So what’s a recently single relationship blogger back on the market to do? Why throw herself at the mercy of her audience and allow them a portal into her dating life AND a chance to sit in the driver’s seat, of course.

That’s right, this content will be interactive. But I’ll come back to that later.

So why am I doing this? Because I hate that I know so many smart, beautiful, amazing women in NYC who are unattached. And yes, though some of it is by choice, many of them have essentially been priced out of the market by an ever-soaring standard of male expectations.

I need only look around a recent Barre Method class to illustrate my point. It was brimming with fit and seemingly successful women who were literally killing themselves to maintain a standard that yes, may be just for them, but also might be an attempt at keeping up with the (Bridget) Jones’ in this city. We’re killing ourselves to stay competitive, to remain optimistic and yet not do ourselves the disservice of lowering the bar. And we’re drowning ourselves in cocktails with our girlfriends while we figure it all out.

If I had $1 for every time I’ve been told, “I know a guy who would be perfect for you…if only he could stop being a dumbass and be a boyfriend,” I wouldn’t have to write this blog. Or at least, I could afford to shop in the expensive cheese aisle at Whole Foods. Whatever.

Back to my point. It’s like men here figure, “Why hang onto that 8.5 when there’s the possibility of a 9.5 just around the corner?” Or settle down at all! Not when the shelf life of the Metropolitan ManBoy doesn’t begin to spoil until at least their late thirties. The Peter Pan Syndrome isn’t new to the New York lexicon, but that doesn’t make it any less disappointing.


So I implore you, gentlemen – and specifically men of NYC – prove me wrong. Show me that there’re guys out there who are smart enough to know a good thing when they see it, and are willing to set down all of the other BS while they get to the bottom of it. Or at least, come along with me during my process of elimination – it’s sure to be a fun ride.

I’m hopeful that such a dude exists. The question right now, however, is where to find him?

Actually, there are lots of questions. So let’s start with the basic parameters of the Holy-shit-remind-me-why-I’m-doing-this-again Miss Wingman Good Man Experiment, shall we?

First things first: What defines a good man? For the purposes of this experiment, it’s a man who’s charming, outgoing, intellectually driven, mature (but doesn’t take himself too seriously), reliable, witty, committed and who – for lack of a more elegant way to put it – has his shit together.

How does one go about finding him? The fuck if I know! Amirite ladies? But I’ll be comparing all of the different ways a woman dating in New York may stumble upon her game changer: through mutual friends, sites like Match.com, dating apps like Tinder, coworkers, and good old fashioned happenstance. Read: encounters in the grocery store, coffee shops, the gym, bars – even on the F train. And yes, that actually happened to me.

Are the guys going to know they’re part of this experiment? Initially no. Not on the first date, at least. I’ll tell them I’m freelance journalist, which is true. However, if we hit it off or if I think there’s potential there, on the second date I’ll disclose that I’m a relationship writer, and that any men in my life are fair game for content. That should go over well.

How will they be evaluated? Think player stats, like Fantasy Football for dating. They’ll also be rated on Wingman scale of 1 to 5, with truly outstanding bros receiving five Web‘s.

How is it interactive? In this Choose Your Adventure: Dating Edition, readers will be helping me decide who to set up dates with or chat up based off of biographical information. And yes, names will be changed to protect the innocent (I’m not that much of a dick.) I’ll also let you help me decide which of my photos to post, or what to say in my profile. It’ll kind of be like Romantic Mad Libs, only instead of your little brother filling in the blanks with scribbles, you can fill them in with potentially awkward suggestions for me. Yayyyy.

Is anything off limits? I reserve the right to omit someone with whom I’d like to preserve a potential friendship (or with whom our lives are too intertwined), in the interest of not committing social suicide. I’ll still be a mostly-open book though, promise.

Can the guys be from outside NYC? All five boroughs, Long Island and especially-close areas of CT and NJ are fair game, since I’m considering them to be in the “Greater NYC area.” Congratulations on becoming newly relevant to me, Jersey. Let’s hope your male talent is more impressive than your professional sports teams.

Will Miss Wingman still be posting other, unrelated content? You bet. It was just high time that my female readership got in on the action, too.

So that’s it, amigos. Yes, the revolution will be televised (figuratively, at least), but if you don’t want to miss out on any of it, subscribe to Miss Wingman or follow along on Twitter. Consider this me kicking the door to my life wide open (yikes), inviting the crazy in (hopefully not), and setting out the welcome mat (God help me) in search of good men in New York.

Until then, if anyone needs me, I’ll be just winging it.THAT’S WHAT SHE SAID

Facebook Twitter