GIRL FACTS: THE SAGA CONTINUES

Girl Fact: We have underwear that serve specific functions. Like the I’m-Doing-Laundry-And-These-Are-From-Before-Christ pair we throw on in the meantime, the Comfy-And-Won’t-Give-Me-A-Wedgie pair we wear when we’re out of commission, and the Really-Uncomfy-But-I-Don’t-Care-I-Look-Hot-In-Them pair we wear when we think we might be bringing a guy home. Those are not to be confused with the Don’t-judge-me-for-buying-something-so-slutty pair that every girl owns. True story.

Girl Fact: We all secretly hate Blake Lively.

Girl Fact: Sometimes girls who say they like sports go to bars to “watch the game.” How can you tell if she’s an impostor? Block the screen and ask her what the score is, what number the star player’s jersey is or what color each team is wearing. Chances are she can’t tell you.

Girl Fact: We have a favorite amongst your friends, we also know which one we think is the hottest, and we’ll probably never tell you either one.

Girl Fact: We like to sing loudly while in the shower or driving in our cars, usually to guilty pleasure music like Taylor Swift, Gaga or Katy Perry. And no matter how unfortunate our singing voice is, in our minds we sound exactly like Kelly Clarkson.THAT’S WHAT SHE SAID

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JUST WING IT: WINGMAN PROTOCOL FROM BOTH PERSPECTIVES

Let’s face it – the dating world is a dangerous place. It’s full of conversational land mines, social mishaps and the occasional grenades to dodge (in the Pauly D sense of the word, that is). Thus having a wingman is not only necessary, but a huge help in chatting up the opposite sex.

You need someone to help you with your approach, engage in playful rounds of verbal sparring so that you seem witty, and chat up any friends your target has in tow to free you and your intended up for a love connection. Someone to be the Goose to your Maverick, if you will. But what are the rules of such a set up? This is where things can get tricky.

A friend recently sent me an email detailing her distaste for the way a man behaved while she was serving as wingwoman one night. She said the gentleman attempting to win over her friend virtually ignored her – the cardinal sin men can commit in a social setting. Be nice to the friend, be nice to the friend, be nice to the friend – always, and under all circumstances.

Because after all, when you walk away, if you’ve rubbed the wrong way the one who will have her ear on the ride home, you’ve just shot yourself down and all of that hard work was for naught. So here are a few behavioral guidelines for those chatting up someone with a wingman in tow, as well as for the wingman (or woman) him or herself. It’s not rocket science, but it needs to be said.

Be inclusive, not exclusive - If the person you’re talking to has a friend (or friends) with them, as I said, make sure to engage them in conversation as well. Or, at least make eye contact while you’re talking to the one you’re really interested in, so that they don’t feel like human furniture. Eye contact or nodding when they talk is just as effective an interaction. I can’t emphasize this enough.

Even if you are underwhelmed by said friend, this will make the friend think you have manners, and possibly rally in your favor later on if he or she thinks you’re particularly funny or charming. If there is a momentary lull in conversation, ask how they know each other, chat up the friend about what she does for work – whatever, just keep the exchange going as long as possible to gain an opportunity to showcase your personality.

Smile - There is nothing as disarming as smiling at someone. People should do it more often, in my opinion. So, if you’re talking to a woman you’re into, make steady eye contact, smile (not in a goofy, cartoon-ish way though) and be as relaxed as possible. It’s just a conversation, don’t over-think it.

Offer both of them a drink - If you notice that one or both of the women you’re chatting up has a drink that could use some refilling, take the initiative and ask to buy them a round. I know this isn’t an inexpensive or convenient move, but it shows us that you have manners, a rare commodity these days.

For those serving as wingman/woman - It becomes clear fairly quickly who the intended target is, so if it’s established that it’s your friend’s affections that are being sought, you have some responsibilities as well. If you seem to like the person who just approached (or at least don’t abhor them instantly), you would do well to help him or her out. It’s good karma.

If there is an awkward silence, jump in and ask a question, like, “So, what does a (fill in the blank job) do exactly?” *Note, obviously if the person has an easy job, like a dentist, that’s pretty self-explanatory. Don’t inquire unless you want to look slightly challenged in the smarts department.

Or you could talk up your friend if you think that he or she could use some help closing the deal. Casually bring up something impressive about them, or if he or she is particularly funny take a cue from earlier and do the whole witty banter thing. Verbally tag-teaming your friends makes you both look approachable and reminds us all of our own friendships, which helps put people at ease.

But whatever you do, try to avoid cutting the poor person at the knees and forcing them to walk away with a bruised ego and shattered confidence. It takes guts to approach someone, after all, and that type of bravery should never be scoffed at or insulted – unless the person approaching is particularly lecherous or annoying.

In that case, the wingman should fake an asthma attack or say something to your friend like, “Hey isn’t that your girlfriend (or boyfriend) over there?” and then point to the most intimidating-looking person in the room. Then make a hasty escape.

It shouldn’t be that hard to meet people, we do it every day in various circumstances. It is, however, hard to meet people of substance, worth keeping around. So if you’re on the prowl or just keeping a buddy company, remember that some rules of decorum apply. And if you can’t be helpful or straighten up and fly right, perhaps you’re better off staying home.ETIQUETTE WINGMAN

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ONLINE DATING HORROR STORY OF THE WEEK: A MALE PERSPECTIVE, FINALLY

After weeks of girls offering up stories about caffeine freaks, guys with weird fetishes and men who won’t come out of the closet, a male has finally stepped up to the plate this week. Halleluiah – a dating story about a woman, what a novelty. This one’s short and sweet, and brought to us by “Matt from the Upper East Side.” Um, okay, you could’ve just said New York, Matt. But here goes:

Ali, the ad sales girl: “Started talking to this girl on Match (my sister convinced me to sign up), but the photos of the girls on there were pretty hot so I figured it would work out one way or the other. Her picture was especially pretty, so I emailed her and she agreed to meet. We went to a sushi place in her neighborhood, I pulled out her chair, paid for both of us, asked her questions about herself. All of the things guys are supposed to do on dates, done.

Wanna know what she did wrong? Get a pencil and write this down – women should hear it. First of all, she looked nothing like her profile picture, or at least maybe she did…15 years ago. The entire time we were talking, I kept noticing these girls across the restaurant talking about us and staring over. They were giggling and stuff, it was pretty obvious they either didn’t like my date, thought they knew me, etc. It was blatant.

After a while I just asked her flat out, “What’s the deal with those girls over there? Do you know them?” And finally she admitted they were her friends, who came out to make sure she was alright (what am I, a serial killer?) but were doing a bad job of being under the radar. That made me uncomfortable, and made her look crazy.

Then she spent the whole dinner asking me rude questions that made it obvious she was only into money (“What do you do for work? Oh investment banking, do you have a car in the city? Where do you do your summer share?”). Nice, at least wait until after a few dates to let me know you want what every other girl in Manhattan wants, a guy who will buy you a huge ring.

She also kept her phone on the table the entire night and was texting from time to time (you guys can be rude, too) and made catty comments about everyone who walked by or was sitting near us. Really classy.

Even though I wasn’t into her, I still offered to walk her home at the end of the night, and when I didn’t try to kiss her, she said, “What, is something wrong? Don’t you want to go out again?” Call me crazy, but no. I’d rather rub one out with sandpaper in my palm,  thanks anyway” (*Miss Wingman note: Ew, his words, not mine).

Well, Matt, thanks for your…candor. And for the lovely visual, I’m trying to mentally scrub it away as I type this. But, point taken that women can be just as superficial and uncouth. I’d love to say that I don’t know any women with similar priorities, but that would be a bold-faced lie.

Nice move walking her home (such a dude thing to do, hoping for a kiss even if she was toxic all night long, love it) and as for her friends being there, that takes it to a whole other level of crazy. As a female, I understand the inclination to worry about your safety, but sounds like that surveillance team was there more for her approval than her protection.

Keep the faith, man, this city has millions of women, they can’t all be bad, right? Eh, actually, if gold-digging is your turnoff, you might want to consider moving outside the Big Apple. I hear people are a lot more humble in Delaware.

Have an Online Dating Horror Story to contribute? Think you can one-up those that came before you? Misery loves company, kids. Send it my way, for our reading enjoyment: misswingman@gmail.com.THAT’S WHAT SHE SAID

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LIP SERVICE: WHY THERE’S NO EXCUSE FOR BEING A BAD KISSER…PAST NINTH GRADE

Maybe it’s because New Years Eve just passed and there was a healthy amount of midnight smooching going on between virtual strangers. Or, maybe it’s because the universe just decided to drop topics into my lap lately by having no less than 3 – yes 3 – female friends complain about recent misadventures of the lip-lock variety. Whatever the reason, I’m taking a stand. Listen up, men: There is no, I repeat NO excuse for being a bad kisser at this age. (*and if you have to wonder if that term includes you, then keep reading…)

Are you 15 and awkwardly making out after school before her parents get home? No?

Then what gives.

One would assume that, whether you’re in your twenties, thirties or beyond, at this point you’ve been in at the very least one serious relationship, so you’ve had constant access to a partner, and ample opportunity for practice. Even if you’ve never been the serious relationship kind, you’ve likely had more than a few dalliances with the opposite sex by now. So, when women are openly voicing their disgust amongst each other, you’ve got some ‘Splaining to do. And I’ve got my work cut out for me.

Every so often I stumble across articles where Ask-A-Chick types give advice to men about techniques in bed or foreplay where they use creepy descriptive words and make you feel like you’re reading soft-core porn. Not my style. What I can tell you is that, if you take nothing else from this or read no further, hear this: slow down. SLOW. DOWN.

There’s a time and a place for aggressive, Mountains-Of-Pent-Up-Sexual-Tension-Between-You-type make out sessions. Rolling around and hair-pulling is all well and good, when it’s called for. But, for the most part, you want to slow down and enjoy each other. So take your time, if you please.

What We Hate: I know a guy who’s nickname amongst the females who knew him was “Rape Mouth.” Yup, it’s true. I said it – and I do so with complete knowledge that making light of rape in any way, shape or form is not OK, so my apologies for repeating this not-so-PC phrase, but it’s for educational purposes. And no, despite being a smart ass, I did not coin the term. He earned that name because he had a tendency to shove his face into yours and gnaw away like you were an ice cream cone that was about to melt at any minute. Afterwards, you felt violated.

The takeaway? Please don’t press your faces up against ours so hard. Please remember to pull back and take a breath every once in a while. Please don’t lead with your teeth – ever. And please stick to the actual vicinity of her lips. I also know a story about a girl whose face was licked during a make out session like he was a Golden Retriever (or Charlotte, below). I am still traumatized from hearing her tell it.

What We Like: I can’t speak for every girl, but I can tell you that for the most part women like a confident kisser. You know you’re confident when you can put little pauses in the action, playfully bite her lower lip (I said playfully – light and infrequent is the key) or put both hands on either side of her face.

There’s something about seeing a man kiss his woman while holding her face that is just too sweet – like he really, really means it. If none of this is your style, then feel free to improvise. Kissing shouldn’t be choreographed, it shouldn’t feel contrived, and it should vary greatly from one partner to the next. After a few seconds of it, you’ll be able to tell her style and, if you want, take her lead.

Please try to keep the spit thing under control, and for god’s sake don’t cram your tongues down our throats. Remember also that we wear lip gloss/stick/makeup in general, so there’s a solid chance that, if the kissing was extensive enough, when you pull back and look at us we may look a little…worse for the wear.

Likewise, if you have stubble or facial hair, don’t be surprised if our face looks like the skin equivalent of furniture stripped with sandpaper afterwards. Ouch.

I can’t even believe I’m having to lay this all out for you, but apparently some guidelines were in order. Also, fret not – I’d say the vast majority of men fall squarely in the “you’re doing fine” part of the bell curve. But if you were worried that you’re an outlier, perhaps this will help.

Whatever your method, remember this – kissing should be fun, and you should do it often. And if you needed this refresher course to get you back on track, don’t worry, it’ll be our little secret. I promise – my lips are sealed.THAT’S WHAT SHE SAID

 

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THE WAIT: HOW LONG TO HOLD OFF BEFORE TEXT/CALLING HER

If you know the expression, “A watched pot never boils,” then you’re probably familiar with how true it can be in matters of waiting for the phone to ring…er, message indicator to buzz. Whatever.

Let’s say you met a woman worth following up with this past weekend, and she gave you her number. How long should you wait before throwing out the first casual-yet-witty text? It depends on the circumstances, but I’ve got you covered.

In a perfect world, no one would play games and try to choreograph our interactions, they would just call when they felt like talking to you, text if they were thinking about you, and make time when they wanted to spend time. Unfortunately, that’s not the planet we live on. We’re all inhabitants of the land where Should-I-or-Shouldn’t-I intrigue is of the utmost importance.

Though there are exceptions to every rule, there is a general framework you can work off of, and ways to tell what it says to us if you take those routes. So listen up, and weigh in. You might just learn something.

The scenario: After you first met her. The wait: No more than four or five days. Why? Because your meeting is still fresh enough in her mind that she’ll recall you, but not so fresh as to seem overeager. What’s too soon? An argument can be made for the next day maybe, but honestly, even that’s not terrible to many of us. Better instead to send an immediate text, perhaps on your way home, saying “Nice to meet you, so-and-so.” Then, you’re off the hook for a bit and can plot your next move.

When have you waited too long? Eh, I’d say if you let it go a week you’re pushing it, honestly. And if you’ve surpassed a week, you might’ve missed your window. Waiting two weeks tells us that you haven’t met anyone better the past few weekends, so maybe you’re dipping back into your phone now to see what we’re up to out of boredom or convenience. No guy who’s really into a girl will be able to hold out that long, and we know it.

If your life is just particularly crazy during that window, throwing out a preemptive message is a solid, solid move. Try something like, “Hey it’s (your name). Enjoyed meeting you and would still like to catch up soon. This week’s a bit hectic, just putting next week on your radar if you’re into it. Will hit you up when things calm down.” You’ll put her mind at ease and buy yourself time to actually let things settle.

On the flip side, if you were just waiting for the next weekend to come along as the impetus to hit her up, beware. While this makes complete sense, it can give the impression that you’re waiting until a Friday or Saturday because you want to meet up late night. If she’s even remotely worth keeping around, she won’t let you try to fit her into that category, especially not straight away. Unless of course that’s all she’s looking for, too.

The scenario: Post-first date. The wait: Somewhere between two and four days…five tops. What’s too soon? Nothing, really. You can easily get away with texting her the following day. Just as long as your messages aren’t constant and persistent beginning mere hours after you meet. When have you waited too long? Over a week says, “I’m just not that into you.” You know it, we know it, it’s that simple.

The scenario: Post-first time hooking up. I realize that people’s definition of this term varies greatly, but I’d say it doesn’t really matter how extensive it was, if anything more than garden variety kissing went on, the rule still applies. Were clothes removed? Did she stay over? These all just up the ante here, men. How long? The next day.

Hear me? The. Next. Day.

Unless you had something going on that day that she’s aware would be keeping you busy, you should never allow a woman to feel vulnerable post-hook up that there’s a chance you were just in it for the chase, and now that you’ve gotten it, things are going to anticlimactically and unceremoniously fizzle out. Call me old fashioned, but this is how it is. Making her have even a moment of regret that she gave it up is the surest way to make her not trust you. After that, all bets are off.

For that matter, you may be asking yourself why you have to be the one to reach out at all? Why can’t she text or call you first? Because you’re the man, that’s why. I’m from the school of thought that this makes it your job, and I know I’m not alone in that thinking.

You could take this a step farther and ask how long you should wait to call or text post-fight, but that one’s not even subject to standard timelines. Wait as long as it takes you to ensure that when you speak with her, your thinking will be clear, your temper will be in check, and perspective will be kept in mind. If you feel like you’ll make a bigger deal out of it by jumping the gun before you’ve simmered, sit tight.

That’s it, for the most part. I’ll restate just for emphasis the fact that there are exceptions to every rule, so don’t think because you deviated from this that you’re done for – not so. These set ups are really just nerve-wracking when it hasn’t been established yet how you feel about each other. They’re only tough in the beginning. After that you know what she considers you, how she feels about you and what her reaction will likely be, so use those as your north star from that point forward.

My motto has always been, is now and never will go wrong being: Don’t pay attention to anything he says, just pay attention to what he does. Anybody can talk a good game, that’s easy. But backing it up is a whole different ballgame. If you’re serious about keeping her in the fold, you have to start out by fostering trust on both sides, it’s the only way. Good luck, God speed, guys, and go out there and get get your girl.ETIQUETTE WINGMAN

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THE EX-FILES: WHAT WE DON’T WANT TO HEAR ABOUT YOUR FORMER FLAME

The holidays are a time for reflecting. But what if, while looking back, there’s a figure in your rear view mirror that your current passenger isn’t too thrilled to hear about? When it comes to exes, there’s a fine line to put us at ease about how you regard her; Too fondly may mean you two still talk often (or hang out – which doesn’t sit well with most women). But, if you never mention your past, you may have us wondering if your love ended with a restraining order, or if she’s currently at the bottom of a river somewhere? No one’s so detached that you move on and nary breathe a word, after all.

Whatever your status with your former flame, there are a few things that your current (or potential) love interest will be none too pleased to learn about the One That Came Before. Just like most men don’t want to hear that our ex is the heir to a (fill in the blank) fortune with McConaughey’s good looks, Gosling’s sensitivity and the anatomical endowments of Wahlberg in “Boogie Nights,” there are certain things we hate to hear, too. So if your ex fits the following bill, perhaps it’s best to play your cards close to your chest:

A Model of Any Kind: Whether her bod graced the pages of an LL Bean catalog or, God help us all, a Victoria’s Secret glossy, why not do us a favor and keep that your little secret, too? Normally I’d tell you to always be up front, never lie by omission, but in this case that news may just mess with her head more than any normal woman can handle. No matter how confident a female is, we almost always compare ourselves to our peers. And, if you inform her that her peers now include genetically gifted chicks who don lingerie for a living, her head may just explode. Seriously, how would you feel if we told you we used to sleep with a Ryan Reynolds look-alike (or worse, the real thing)? Mum’s the word, boys.

A Do-Gooder: Does your ex volunteer for the Peace Corps? Is she healing the world one under-developed country at a time in Doctors Without Borders? Does she rescue orphans from war-torn regions? Yeah, this is a little too Angelina Jolie for your average woman to handle. It’s one thing to volunteer her time on a relatively local level – many of us do that, and enjoy it immensely – but if she’s off globetrotting or started her own Nonprofit, those are some big shoes to fill. We should all do good just for the sake of doing good, but that bar is set pretty high, don’t ya think?

She Lived With You (or worse, you two were engaged): No one takes a relationship to that level unless you’re really serious with that person. People break up and move on every day, but there’s something about the permanence this once showed that makes it hard for the one who’s with you now to ever feel like she’ll be as much of a presence in your life. Sad but true, and tricky to work around.

A Semi-Pro, Pro or Otherwise-Gifted Athlete: Two words, David Beckham. OK fine, maybe that’s not a fair comparison…But seriously, girls who have skills on the field or on the court are a tough act to follow – even if her name isn’t Hope Solo or Maria Sharapova. And being a female who’s good at something sports-related is about as good as it gets (unless she’s built like a Williams sister or is gender ambiguous, a la Beijing Olympics – not hot).

Granted, we know we shouldn’t worry about making such comparisons, but would you like it if she told you Once upon a time she dated Derek Jeter or Mark Sanchez? Or C.J. Wilson, or Cam Newton (I could go on and on here boys…) Right, didn’t think so.

Bi-Sexual or just Bi-Curious: We’re aware of your fantasy to see us with another girl, but if your ex actually WAS with another girl, that’s not just dipping our big toe in to test the same-sex waters, that’s diving head first into the deep end of the pool. I’m all for people being with whomever makes them happy, male or female, but that little tidbit may just make her feel like she’d never be seen as adventurous enough to entertain you in bed.

An Identical Twin: You boys and your fantasies again… We know, twins are twice the fun. So, even if you only dated one half of that novelty pair, at some point you still swam in the Doublemint Commercial pond, and probably liked it. Nothing we can do about this one, but still not terribly reassuring.

An Adrenaline-Junkie: Was she A) a pilot, B) a race car driver, C) an extreme sports enthusiast (read: she loved skydiving, motorcycle riding or snowboarding half-pipes) or D) a crack shot with a firearm? If so, we will immediately begin to wonder why you are now dating a regulation female like us. Even if your ex’s adventurous ways were too much for you to handle, it’ll still be hard to hear that you once shared a bed with a badass.

A Singer or Actress: This one is less “actress,” since the definition of that word is shamefully loose these days, and more “someone in the public eye.” If your ex had Adele’s pipes or used-to-be-on-that-television-show-about-that-guy, those types of run-ins are hard to avoid. Even if you swear that you’ve learned to resist her siren song, your current beau might not believe you. And she might have to stop watching TV or listening to the radio, too. Would you like it if our ex was a triple threat, of the Timberlake variety? No one would, hell I’ve known straight males who crush hard on that guy. But you get the idea.

Granted, in a perfect world your relationship record would be expunged, and we would all forget that anyone came before us. Women – and men, for that matter – prefer to feel like they were the first pioneers to, er…explore your land. But that’s not realistic.

Don’t ever lie about your past, lest you seem like you’re making a bigger deal out of something that wasn’t. Just realize that, once you’ve told us your ex fits into one of these categories, it might take us a minute to process the news. Then, it’s out there and you should answer any questions she has about it, but don’t dwell on it – move on as quickly as possible.

Making the one you’re with feel like she’s the only one that matters is important, but it’s also a two-way street. If you reassure her and she’s still stuck on it, or can’t shake her insecurities, then you’re dealing with a much larger problem. The confident woman will always prevail…just as long as your ex’s name isn’t Giselle.THAT’S WHAT SHE SAID

 

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“DID THAT JUST HAPPEN?” WINGMAN

Rarely am I left speechless, but an incident last night did the trick. In the nearly nine years that I’ve lived in NYC, I’ve never had an encounter quite like the one I’m about to tell you. Naturally then, I had no choice but to turn it into fodder for the masses, for two reasons: A) So that you boys can learn something from the rogue behavior of one of your own, and B) So that my entire reading audience can weigh in on whether this guy is brilliant or just straight up insane.

“Picture it, Sicily, 1927…” Just kidding. I couldn’t resist the urge to make a Sophia on “The Golden Girls” reference – which hopefully wasn’t lost on you. Ahem. Sorry, where was I?

Right. I was walking through Manhattan’s Union Square last night around 9pm, having just finished some Christmas shopping errands, on my way to the gym. Suddenly, a guy came up behind me and ran out in front of me, stopping me and waving his hands. “Hold on, wait wait wait – can you stop for a minute?” he asked. “My name is James (changed for privacy), what’s yours? I just saw you walking and thought you were really pretty. So I wanted to come talk to you, I needed to introduce myself,” (or some slight variation, it’s as close as my memory can recall).

While I stood there, dazed and slow blinking in shock, I immediately looked around for either John Quinones from ABC with a camera crew, or for a con artist sidekick who would inevitably be rushing up behind me to steal my wallet any moment now. Maybe it’s a New York thing, but my first impression was to check my pockets. This couldn’t be for real.

Turns out it was. Dude literally ran down a stone cold stranger in the middle of a busy intersection and proceeded to try and pick me up – gym clothes and all. *Note: I’m not the girl who wears cute clothes to the gym, never have been. In fact, I was wearing baggy track pants, an athletic department-issue T-shirt from my college and a hoodie – hardly Workout Barbie attire.

So, since a large part of my interaction with all of you hinges on whether or not you can meet girls in various places (like the grocery store) and how to approach us, how could I in good conscience not turn this into a tutorial? Thus, here are the answers to the questions you’re probably asking right now, in no particular order…

What did he look like? He appeared to be normal, probably late twenties, wearing a button down shirt and overcoat – which he explained by the fact that he’d just gotten out of work. What did I do? I couldn’t stop laughing, and then once I realized he wasn’t kidding I flat-out blurted, “Is this what you do? Did you really just run down a complete stranger?”

Then I informed him of his grievous misfortune in choosing the one female whose job requires that I spin this and possibly use it against him (or not, that’s still up in the air). He thought it was funny, I told him he may not be laughing for that long. And PS, he knows the name of this website, so if you’re reading this, James, let’s see how much of a sense of humor you really have now…

What did we talk about? He lead off by asking me what my nationality is – and choosing correctly (I am ambiguously ethnic, so it was a decent guess). Then he quickly looked for common ground and told me he was partially that nationality as well. He started using anything he could as fodder for conversation – “Oh you’re going to the gym, are you a runner? You look like a runner,” and on and on. How long did this interaction last? About ten minutes, three or so minutes into which he managed to appear disarming enough for me not to run away.

So what happened next? He told me he wanted to take me out for coffee. Boys – take note: he didn’t just loosely throw it out there, he told me when he’d be back from the holidays, and attempted to nail down a date and time. His persistence was actually fairly impressive, and I had to congratulate him on his bravery (even if he is totally full of it). Any guy who pulls a play like this deserves some respect if for no other reason than that it’s such a bold move. I had to tip my hat (and check for my wallet at least two more times).

He asked for my number, upon which time I told him that I don’t give my number out to random strangers in the craziest city in the world. He wouldn’t give up though, and eventually…sigh…I relented. Yup, that’s right, the most critical female of these sorts of moments finally gave in and gave him my digits – the real ones, since I know you’re wondering. Even I can’t believe I did that, actually.

In all honesty, he said, “OK so it’s a date,” and I responded, “Actually it’s more like a case study. I have to figure out where your head was at when you did this, I’m stunned,” which may be most of my motivation should we ever actually speak again.

So now what? Am I crazy? Is he crazy? Am I about to be the victim of some corporate-type, harmless looking con artist, or was he just a guy who saw an opportunity and seized it? You decide, and please weigh in.

I realize how flawed my “he looked normal enough” rationale is, especially since that’s how Ted Bundy got away with picking off dozens of women. But, what he had working in his favor was that he appeared similar to someone I’d be friends with, a fairly regulation NYC male. I am still highly skeptical of his intentions, partially flattered but mostly just not buying it. Again – almost no makeup, hair in a ponytail, Rocky Balboa clothes. But, out of curiosity I stuck around.

So now I flip the script on all of you for once and ask for your feedback. Would you ever try this method, which is essentially the dating equivalent of a cold call? What in the world could possibly be someone’s motivation to do this? Do you think other women would be averse to this or play along, too? Hit up Miss Wingman’s handy dandy comments section or email misswingman@gmail.com and weigh in, please. I have a feeling this is going to be fun… THAT’S WHAT SHE SAID

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