From eating cookies on prom night, to flirting in Manhattan meat markets?
March 9, 2008 3:26 PM   Subscribe

After a complete transformation, I need to practice flirting, in New York.

I'm in my early 20s and I recently lost a lot of weight. I was not a fabulous fat girl, so I've never really been picked up, hit on, or flirted with, and now I'm not sure how to respond to any of the above -- let alone reciprocate. I mean, I've read plenty online, I'm socially competent, I have plenty of friends (girls and guys), I'm told I'm funny and fun, and I don't think I'm going to embarrass myself. I hope. I do have some recently acquired physical experience thanks to a good friend, and although that's not complete, the real problem is that missing out on all the years of normal teenager-development stuff means I need practice flirting, basically. I'm not even sure how to look approachable. I am also really, really criminally bad about not being able to turn down anyone who's interested in me.

I'm going to be in New York in a few weeks. I think it's the right place to start -- I'm familiar and comfortable with the city, but because it's not home base for me, I'm not going to run into the same people again, and I'm not going to worry about whether flirting will turn into more. I can just relax and practice low-stakes flirting.

I'd really like an idea of somewhere to go, where it's likely guys will try to flirt with me. If I were looking for a serious relationship, I would just do stuff I enjoy while being open to meeting people, or maybe I'd make an effort to go to readings or talks or other intellectual stuff. But my goal here is not just likeliness of awesome guys, but also frequency of flirt attempts. However, more intelligent crowds would still be great -- I don't want a total B&T meat market vibe. Somewhere everyone's looking for a one-night stand wouldn't be as right as somewhere people are openly looking for something that could be more. I have business during the day, so after-work bars (or whatever) would be great, but I'll be there over at least one weekend so that's fine too.

Also, although I might be pretty cute now, I'm still not a stunning model wearing high fashion, so I'm not going to get entrance to that kind of scene. I'm not good at judging myself, so all I can do is say that with a fair picture of me in a sweatshirt, Hot Or Not rates me about 7.5. (No, I won't be wearing a sweatshirt out -- more likely a fitted sweater with jeans or a skirt.)

Bonus complication: Because of my previous addictive behaviors with food, I don't drink. I have no problem going to bars or being around people who are drinking, but if drinking is the only thing to do, or if everyone there is going to be really drunk, that's not as much fun. Plus if guys have beer goggles on, I can't believe they're into the actual me.

Basically, I'm looking for a few different things. In no order:
1) advice/experiences of people who have gone from ugly ducklings to semi-swans around this age
2) advice in general about how to flirt, how to attract interest, etc.
3) recommendations from New Yorkers about what specific places would be right to go to

Thanks, everyone!
posted by anonymous to Society & Culture (20 answers total) 17 users marked this as a favorite
Flirting is basically showing interest without seeming like a dangerous creep. Try just looking at someone a touch longer than feels comfortable. Flirting is game. It's not a contract to go home with someone just because you've smiled and chatted, so take your time to decide if you want to talk. People who are into flirting like the game. Go nice and slow. And be mellow. A large part of it is being cool, so don't feel like you're not that hot if it doesn't go well at first.

I don't know you, and just so you know, i'm no swan. I do hope you can use this as playful way to take some time to decide what you want when someone shows interest in you. Guys try to exploit women by calling them teases. Don't let them do this to you.
posted by gesamtkunstwerk at 3:44 PM on March 9, 2008

You don't go to specific places to flirt, you do it everywhere -- from the guy at the newsstand to the bellhop. Flirt all the time, low-level, and when you need to rock it, it will come much easier.
posted by bonaldi at 4:01 PM on March 9, 2008 [3 favorites]

gesamtkunstwerk writes "Guys try to exploit women by calling them teases. Don't let them do this to you."

Not all guys do that , please remember that. One good idea is to avoid generalizations , look for evidence. Not all man do X, not all woman do X. If he rejects you as if you teased him and them dropped him, but you know that you were not trying to tease him at all, then it's all in his head and it's all his problem, you were not being rude or manipulative. Be honest to yourself first and foremost, take your time, it's supposed to be fun not another form of competition anxiety.

Consider that there is whole lot of guys and girls out there that are pretty much scared and don't really know how much they are , they may close up suddendly without giving out any idea why , you may think you did or say something wrong. Consider that you, as well, may have insecurities that you are not really aware of and you may spout unwittingly some remark that may sound "not nice" to somebody. Don't blame yourself too much for it, because you didn't want to do it, but it's quite interesting to figure out why you said what you did...sometime we spout defensive stuff...some boy go "eheh I am no shit taking man, they can't fuck with me" ..which betrays that he could be somehow scared by something.

That's utterly normal, but unfortunately some men are taught they should act as if they were Macho Man and that showing weakness is a turn off for girls who wants self confident dudes. They are also taught that not being succesful (getting laid) with a girl is a sign of rejection and are taught to knee jerk react to it and treat the girls as manipulative bitches, act offended and indignant, to cover up the fact tom themselves they have issues dealing with being said "no thank you" ,they feel invalidated.

I think you may find a number of these guys in date situations, as they are told to go hunt for babes and learn to deal with rejection by experiencing a lot of it...which of course doesn't work, it only makes them more angry. Don't be put off by them or think that most men are like them only because you met a number of people like that

Clearly it becomes a self fullfilling prophecy for them, because they start acting as jerk without realizing they blanket is actually harming them. They could use a lot of help and some of them eventually wises up , much like some girl that jumps on anything with pants on to validate her own femininity or to show her female friends she can get anyone she wants in a snap, no problemo..or that remains hooked to an abusive man because she's too scared of going away.

But you also will meet people like you that is just looking for a good chat and maybe develop some sympathy and whatnot.
posted by elpapacito at 4:29 PM on March 9, 2008

Oh I forgot : one excellent premise is to go have FUN, meet people, chat and figure out yourself a little and if it doesn't turn out in an instant "success" oh well , don't jump to the conclusion something is necessarily wrong with you because all the other people SEEM to be having fun , getting laid and generally having the sex life of superstars ! It's attractive because it's a fantasy ! :D
posted by elpapacito at 4:32 PM on March 9, 2008

If you go to the Grey Dog's Coffee on University Place a few times, I or my friend Jon will almost certainly flirt with you. And if we don't, other customers or the very cute guys who work there will. And this is the best and nicest kind of flirting: a quick smile in recognition of a shared "wow, it's cold out!" or "aw, what a cute dog/baby" or even just "hey, we both look pretty good". Or, "can I borrow your syrup?" or "may I look at your Styles section?" or, really, any of a million excuses to strike up a conversation. On weekends there's a line to order food, which sounds annoying but is perfect for casual chatting before you find a table - maybe next to each other, or even together since it's crowded! Also, the coffee and food and atmosphere and people-watching are all excellent; and you'll be very comfortable since they serve beer and wine but it's not a bar, and flirting there isn't aggressive or hookup-oriented. It's exactly what you described above.
posted by nicwolff at 4:38 PM on March 9, 2008 [1 favorite]

A key rule of flirting - no one cares about your baggage but you. You used to be a bit chubbier and a little romantically awkward? No one flirting with you today is judging that. They all have memories of their own self-conscious, pimply adolescence. And they are rockin' the flirting action. What's holding you back?

I was a duckling-to-sort-of-swan myself. I never learned to flirt, but I was always very interested in people - smiling at people, chatting with strangers in line, etc. One day I told someone that I didn't know how to flirt and they laughed at me. Flirting was what I'd been doing all along, but I didn't put that label on it. When I got thinner and more polished, suddenly men responded to that friendliness as flirting. My actions didn't change; their reactions changed.

My best advice on attracting flirting attention is to be unhurried and be available to chat. That means no huddling with 4 girlfriends. Don't be buried in a book so that no one will disturb you. Smile when someone is appealing to you. From there you can just let the flirtiness flow.
posted by 26.2 at 4:53 PM on March 9, 2008 [2 favorites]

I read somewhere that, anthropologically speaking, the definition of "flirting" is "mixed signals".

If you look someone directly in the eye and say "I like you"? Not flirting.

Flirting happens when part of your posture says "I'm not interested" but another part says you are, for instance, your face is down, sending demure "please don't look at me" body language, but your eyes are looking up in an "I'm interested" signal. Or deliberately not returning someone's look, but smiling to show that you know they're looking at you. Or the classic, saying "you're terrible!" when your face and body language show the opposite.

Bit of a geeky approach to the problem, but maybe it'll help.
posted by AmbroseChapel at 4:54 PM on March 9, 2008 [9 favorites]

Ok. I can help you here!! I lost 150 pounds and was in the SAME boat!! Practice is what you need and the best way to do that is with your gay friends. Not sure about where to go for the best Gay bars in NYC but I'm sure that is easy to find out. Grab a friend (gay or not) and go there!! I started going out to clubs with a group of the most wonderful people ever who happen to be gay and got my flirt ON!! It is such a confidence booster to have all these gorgeous men telling you how good you look and how fabulous you are and you quickly learn to accept and give it right back!! The fact that there is no pressure on either side makes it just fun, innocent flirting and that is exactly what you need!! Get you gay friends to take you out on the town several times and flirt, flirt, flirt! You will gain confidence and learn some great tips along the way. It was the BEST thing that I ever could have done for my self confidence and learning how to be comfortable in my own (new) skin! Good Luck!!
posted by pearlybob at 5:29 PM on March 9, 2008 [1 favorite]

1) advice/experiences of people who have gone from ugly ducklings to semi-swans around this age

It's different for women. But anyway, at 7.5 on HotOrNot (try changing the photo a few times), you're way hotter than you think. Enjoy it.

2) advice in general about how to flirt, how to attract interest, etc.

Be nice, smile, be funny, try to find something in people to like, ask open questions, respond to questions with a sentence rather than a word, don't be shy, don't apologize for your own existence, acknowledge that you have sexual interests yourself and are sexually interested in people, talk with some enthusiasm about things that interest you but balance this with keeping the other person participating. Actively participate in conversation. If you like someone and want to pick them up, leaning towards them and smiling, and touching them lightly on the hand or arm is as crystal-clear a signal as you need to give. If that doesn't work, they're probably not into you that way. Which is fine. You yourself aren't into everyone; the reverse applies.

3) recommendations from New Yorkers about what specific places would be right to go to

Not a clue. :)
posted by aeschenkarnos at 5:35 PM on March 9, 2008 [1 favorite]

As far as places to go? just go to the local bar, and no matter where you are in NYC, there's a local bar.

As far as flirting? I've freely admitted to being dense when it comes to feminine signals of interest, but one hi-sign to me was the girl finding an excuse to make physicla contact. Whether it's a tousle of hair or a hand over a hand, the guy will take it as a clear signal of interest.
posted by jonmc at 5:55 PM on March 9, 2008

i hate to be a downer, but there are way more single girls in new york than single guys. my best friend lives in brooklyn and i come to see her a lot. we're both cute girls, but we never get hit on. and yes, we do go out to bars. there are so many gorgeous, model-looking amazon girls in the city, and you will always see one on the arm of a much less attractive guy. basically it is great to be a dude in new york city, but it's slim pickin' for girls.

on the other hand, raging confidence will get you just about anywhere.
posted by timory at 8:15 PM on March 9, 2008

the real problem is that missing out on all the years of normal teenager-development stuff

Only jonmc and people in old John Hughes movies ever got anything out of that "normal teenager-development stuff". Most of us got through our teens very awkwardly without learning too much. You're not really behind the curve. Just act in such a way that you are comfortable and confident with. Regardless of looks, a girl who is at ease with herself (without being stuck on herself) is the most attractive trait in my opinion.
posted by Doohickie at 8:23 PM on March 9, 2008

Only jonmc and people in old John Hughes movies ever got anything out of that "normal teenager-development stuff". Most of us got through our teens very awkwardly without learning too much.

Heh. For the record, I graduated high school a virgin, doohickie (and angry that all those teen flicks had lied to me). My main point was that guys can be kind of thick about signals of interest from women, and that women should be less subtle than they think they ought to be, maybe.
posted by jonmc at 8:50 PM on March 9, 2008

I'm not trying to slag straight guys (specifically, jonmc seems like a well meaning person to me), but they do have different expectations than most straight women. I'm not easier on gay guys, mind you. My point was that it seemed like you were vulnerable to guys who take flirting as a way to get sex. It seems like you need to build up your confidence, by enjoying flirting without taking risks due to perceived expectations. And you don't owe anyone anything for needing to do that.

Disclaimer, I'm gay. I know too many sweet guys who have gotten into trouble because they felt like they owed someone something.

I'd like to see you build your confidence by being cool and playful, but without feeling the need to engage in risky behavior. Please go have fun. But take care of yourself, and don't feel like you have to do anything. Flirting should be fun; it shouldn't make you do anything you don't want to do. Honestly, as a sex positive gay man, I'd advise flirting for a few months before doing anything.
posted by gesamtkunstwerk at 9:11 PM on March 9, 2008

Your plan is genius and cannot fail.

You need a bit of detail. There's a book called Intimate Connections that a Cognitive-Behavioral therapist named David Burns wrote. It lays out exactly how to do it.

A short primer.

First, start by smile practice. Walk around town and smile at potted plants, dogs, and statutes. Next move up to people. Make it a goal to smile at 100 people a day for a week.

Next, when you feel like flirting, make eye contact with men and smile. When you listen to a guy talk, maintain the eye contact. You won't freak people out--they'll want to talk to you more if you look at them. Trust that you won't blow it, because you really cannot fail, as even your "failures" will be successes because you will be learning that even when someone you fancy doesn't like you the same way, you are totally going to survive. Once you obtain this power, you will be invincible.
posted by Ironmouth at 10:57 PM on March 9, 2008 [2 favorites]

jonmc: I wasn't responding to your post (which I had scanned past), I was just referring to you in general. But... graduated a virgin, huh?....
posted by Doohickie at 10:13 AM on March 10, 2008

yeah. spazzy, gawky, homely child with a host of minor defects that pretty much shattered his self-confidence for a long time.
posted by jonmc at 10:30 AM on March 10, 2008

I am in the exact same situation as you OP, except I'm male. I've lost 70 pounds over the last 6 months, got 8.9 on hotornot, and my body image is just beginning to adjust itself to the new me.

I've been using the brute force method. I go out as much as possible and speak to as many people as possible. This has been met with limited success. I've always been generally charming to friends of both sexes, but as soon as I am alone with a woman I'm interested in I turn into a total weirdo.

I still have a very hard time believing anyone could be attracted to me, but I am slowly coming around. As I am figuring this crap out for myself, I don't have that much advice. But I wish you the best of luck.

Home Sweet Home (131 Chrystie St.), is a pretty good bar. I am usually there on Saturdays.
posted by pg at 1:43 PM on March 10, 2008

You really aren't any good at flirting if you submitted this anonymous. Imagine the attention your myspace page could have gotten!
posted by Mr. Gunn at 5:13 PM on March 11, 2008

bonaldi's advice is the best, i promise you. flirting, really, is just talking and being funny and nice, just being comfortable being your own charming self. that's all it is. there is no esoteric formula. i low-level flirt with almost everyone i encounter— be they men, women, children, or dogs, my friends that i will never sleep with, the deli guys that see me every day or a waiter i will probably never see again—and it makes my life easier and better in so many ways not even related to dating or sex.
posted by lia at 9:19 PM on March 12, 2008 [3 favorites]

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