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

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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

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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

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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

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People, please. Control yourselves.

There are some places you just shouldn’t have sex. Like, for instance, on railroad tracks. When a train is coming. And you’re drunk.

In the latest (yes, latest. Sigh…) impossibly stupid and unfortunate case of bumping uglies turned ugly, a couple in the Ukraine just found out the hard way that man’s primal urges are no match for the raw power of a man-made switcher locomotive. This lesson came when it bore down on the pair, who were having sex on the active tracks, killing her and costing him his legs.

Now, I know it’s no laughing matter, but if you’re like me, you’re probably thinking, “What the eff? They couldn’t find a safer place to get it on? Like, say… in the middle of a drone strike, up against a high-rise window, or atop one of those rickety footbridges from ‘Indiana Jones and the Temple of Doom’?”  Ummmmm, apparently not.

Officials said the “30-something woman” and her 41-year-old male companion were walking home from a friend’s party and, presumably, feeling frisky when they decided they wanted to “experience an extreme sensation near the railroad tracks.”

I mean… There’s so much irony in that statement that I won’t even touch it. It’s too easy.


What I will do is offer up arguably the most obvious advice I’ve doled out on this site thus far by imploring all of you to STOP HAVING SEX IN STUPID PLACES. Scratch that – in dangerous places. There isn’t a single sexual pleasure that outweighs the suck factor of having your legs sliced off. Or, like, hurtling to your death. Just cut that shit out already.

Wingman faithful, I’m confident that you possess more self control than a rabbit. Or a high schooler. Or, that you can at least shelve the passion until you get to a place where you and your companion won’t end up as a pun-filled Twitter headline. So please, raise the bar. I know you can do it.

The only upside to this story is that the sex must’ve been so earth-shatteringly good that the couple didn’t even feel a goddamn train bearing down on them (hats off to you, bro.) If you absolutely must check out, I guess there’re worse ways to go.THAT’S WHAT SHE SAID

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While Miss Wingman isn’t usually one for jumping on the pile when the Internets decide to turn on someone (having been on the bottom of that pile myself before), sometimes I can’t help it. Case in point, the 300 sandwiches story.

Not since the 40 Days of Dating stupidity has a couple earned so much of my ire. For those of you who’ve managed to escape the food-related fodder, here’s what you missed…

Woman – who, conveniently, also happens to be a reporter at Page Six – has a boyfriend that likes to cook and has a weird thing for sandwiches. So much so that he begins every day by asking her how long she’s been awake, and when she says, “About 15 minutes,” he responds with, “You’ve been up for 15 minutes and you haven’t made me a sandwich?”

Ugh, I f***king know. It gets worse.

So the woman gives in one day and decides to make him a sandwich (sadly, not a knuckle one like he deserves). A sandwich so apparently amazing that he exclaimed – and I’m horrified that this is a direct quote – “Babes, this is delicious! You’re 300 sandwiches away from an engagement ring!”

Jesus. Christ. If you haven’t just vomited on your keyboard, stay with me.

Now rather than using the knife she just sliced the bread with to play target practice with his junk, she chose to take on that “challenge” of making this dickwad 300 sammies so he’d finally put a ring on it. And, because the world is full of opportunistic, fame-whoring, truly awful people, to blog about it until it went viral.

Recently, she outed her identity and wrote a piece called “I’m 124 Sandwiches Away From An Engagement Ring.” Which, if it’s possible, is even more odious than him calling her “babes.”

Stephanie Smith – that’s her name – justified this endeavor by explaining that, “to him, sandwiches are like kisses or hugs. Or sex.” She said that he believes that “sandwiches are love…you can’t get a sandwich with love from the deli.”

She also pointed out that she sped up the initial 1-sandwich-a-day strategy after she realized that she’d be well into the twilight of her childbearing years before she hit 300 and homeboy finally locked it down (she’s in her mid-thirties.) The horror. So, yeah. That’s it. All caught up. Now if you’ll kindly indulge me while I respond…

Dear Stephanie and Eric,

I know, it sucks to be on the receiving end of so many people calling you a f**king idiot. But, that’s only because you’re acting like f**king idiots. Seriously, what’d you expect to happen?

But while everyone else is content to ream you out for being antifeminist and chauvinistic, I’ll instead offer what I believe is the explanation for your actions. Because at the core of it, Stephanie, I think you’re just afraid of being alone, so you became an enabler. And Eric, while I realize that no man would willingly ever turn down 300 sandwiches, I’m going to side with the crowd here – you actually are chauvinistic. And, frankly, kind of a douche.

Any guy that would make a comment like, “You’ve been up for 15 minutes and haven’t made me a sandwich yet?” joking or not, has something wrong with the wiring in his brain to allow him to form such a thought. Or, he really didn’t mean it, and his verbal filter is so broken that he actually spoke a phrase like that out loud. Neither option’s preferable.

But FYI, your girlfriend owes you nothing. Women don’t earn your commitment – not through food, or blowjobs, or whatever rewards system you believe to be justified. You give the person you love things like respect and commitment because they’re worthy of it. Even if she doesn’t believe that she is herself. Which is the only possibility I can come up with for why Stephanie went along with such an asinine suggestion. She was so desperate to fulfill your happiness that she placed it ahead of her own.

Better to drowsily craft towering patty melts at the end of a long day like some Stepford Julia Child than admit that you’re dating a moron and go back to being single. I’d call her an indentured servant in heels, but she’s hardly being forced into the setup. It’s all just so sad, really.

So perhaps you two deserve each other. I hope that one day men and women will realize that you’re truly better off alone than with someone who doesn’t appreciate you, doesn’t compliment who you are as a person, or doesn’t believe that you – exactly as you are, imperfections and all – are, simply put, enough.

May we all learn something from this distasteful (no pun intended) episode. Good luck to you both. And Stephanie, try spinning it another way. You’re 124 sandwiches away from freedom, girl. F**king run.THAT’S WHAT SHE SAID

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In a perfect world, we’d all find true love, work at places like this (best. company. ever.), Matsui would be a Yankee again, and Ryan Gosling would have me on speed dial.

But, reality can suck sometimes. Which means our expectations aren’t always met, and on occasion, people behave disingenuously. Case in point, a recent study by the American Sociological Association entitled “Who Pays for Dates? Following vs Challenging Conventional Gender Norms” found that (gasp!) sometimes women do things that they don’t actually mean. Things like fake pulling out their wallet to fake offer to pay on a date even when 39% of them admit they’re hoping the man rejects the overture.

I know – worldview blown. Next thing you know the brain trust at some think tank’s going to tell you that women don’t actually like entitled A-holes, either (despite their fancy banker duds.)

After you stop reeling from the shock of it all, I’d like to call your attention to two noteworthy points in this uber groundbreaking story (you win the Duh Award, Slate.)


Firstly, we’ve been over this before, gentlemen. You know my position on who pays. (“hashtag” #dontbecheap.) Also PLEASE STOP SAYING HASHTAG OUT LOUD.

But just in case you need a refresher…

And secondly: wait, exactly how many PhD’s did it take to determine that gender-based attitudes have evolved on some things (like women in the workplace), but not others (like what a man’s chivalrous responsibility is on a date)?

Bitch please. You don’t need a panel of experts and 17,000 survey applicants to figure that out. Drinks with four of my best girlfriends would’ve told you the same thing.ETIQUETTE WINGMAN

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