Remedial Macking
April 9, 2012 11:04 AM   Subscribe

I'd like to hear your thoughts on how one "makes a move" on someone else.

I'm embarrassed to be asking this, even anonymously, but I'm having some difficulties and maybe the hive mind can help. There has not been very much intimacy in my life and for a long time I blamed this on a couple of material obstacles. However, those obstacles have now been addressed and I'm finding that my true difficulties are mental and that I'm going to need to overcome them before things change for me in the way I need them to.

For a long time, you see, I was a really fat guy who was really broke and had no direction in his life. Noting my own low desirability, I assumed that no woman was going to want a fat broke dude making any sort of advance towards her, so in the back of my head this idea started to develop that sex and intimacy and love did not concern me any more than Olympic water polo did - that I was vanishingly unlikely to ever be picked for either. Some version of this thought has been with me ever since high school.

That said, I'm not a virgin. But I've never been the one to make a move - 100% of my sexual relationships have been initiated by the woman involved, almost always to my complete surprise.

Now, fast forward to today: I've lost a ton of weight and am now only kinda fat - barely heavier than your average dude. It took some haranguing from my roommate to make me see it but I'm objectively not nearly the big fat slob I used to be. I'm damn close to normal now. Likewise, there's also been a lot of movement on the career front of late - the money still ain't super impressive but I'm making a fair chunk of it doing something that I really love. In this aspect of my life, it'd be fair to say I'm on fire, that I've got direction and motivation like never before.

I feel like almost all of the factors that need to be in place for me to take a more active role in my love life. The trouble I'm having is that my assumption of my own undesirability seems to have outlived the material causes for it. It's frustrating beyond belief - this isn't me looking to be talked out of self-loathing, I know in the abstract that I've got a lot to offer a woman. I'm a solid, honest dude who dresses well and conducts himself like an adult. Talking to women isn't even the issue anymore - I've developed some small measure of flirting skill and have little difficulty arranging private time with women that interest me. Up to that point, I'm fine.

My problem is that this all falls apart in private, that I've spent years believing no woman could want me and all that old fat, broke slob nervousness still haunts me when I start thinking I'd like to get closer to a woman I'm alone with. I struggle with this even when I've got the strong suspicion that she wouldn't mind me making a move. For me, getting good at being a single guy has meant talking to a lot of female friends about what they do and don't like about men and how they act. So I know that every woman in the world has a few stories about dudes who didn't read her signals right, who went in for the kiss or whatever when it was not welcome and made everything awkward and awful. I really don't want to be a guy who puts women in positions like that. As stated above, I've got no experience as initiator and therefore little confidence in my reading of body language or timing. It'll seem like the moment is right but oh christ, what if it isn't?

So I'll do nothing aside from being polite and pleasant. And eventually, she'll go home or I'll go home. We'll say goodnight and I'll go to bed alone, feeling like maybe I didn't have to. Again. Which cannot continue.

The weight came off and the clothes and career improved because I decided to stop being passive and go right after the changes I wanted in my life. A change to my intimate life is urgently needed but is proving trickier to manifest. I don't want to be passive about this anymore - the results of a lifetime of passivity have been unacceptable. I want to take the initiative here but I'm never sure if I'm getting signals that I ought to or am just misinterpreting things. It's hugely frustrating - more frustrating, almost, than when I could blame everything on my huge fat ass and never spent any time alone at night with attractive women. When the stakes are low, I have little difficulty perceiving myself as I actually am - when they're high, I'm still that unfuckably fat scrub in my head, even though I haven't actually been that guy in a long time.

So AskMe guys, how do you know when a woman you're with would be open to your making a move? And more to the point, how do you do it? God, that's an embarrassing question to type but I'm really lost. Is it really just as simple as leaning over and kissing her and hoping you've read things correctly?

And women of AskMe, what should I be looking for? How do I know when moving in and initiating would be okay? I've been told that outright asking is a pretty clumsy thing to do and yeah, I don't see how a guy just asks "want to make out?" without it being weird. As I said, my experience up until this point has largely been women getting fed up with my shyness and launching themselves at me. I'm working hard on not being shy anymore but I've never initiated and I'm pretty twisted up about it.

It seems like there's talking and flirting between men and women and eventually things get physical but I'm just not sure what those middle steps should look like. And I realize this is probably pretty basic stuff to most of you but I'm having a really hard time with this. Losing the weight was supposed to solve this - it wasn't supposed to last longer than the weight did. Any insight any of you might have would be helpful. I've been struggling for a long time and am deeply unhappy about the lack of intimacy in my life. It feels like I'm really close to competent now which makes the remaining ineptitude all the more frustrating. Please help if you can.
posted by anonymous to Human Relations (49 answers total) 26 users marked this as a favorite
Is it really just as simple as leaning over and kissing her and hoping you've read things correctly?

Yes. Yes, it is.

It seems like there's talking and flirting between men and women and eventually things get physical but I'm just not sure what those middle steps should look like.

I'm a chick; one of the things that I've always read, and can confirm holds up, is a body language thing -- "accidentally" touch her a couple times while you're talking. You know - you touch her shoulder to get her attention, you're in the middle of a story and you touch her arm when you say "Oh, yeah, and then THIS happened..." or whatever, you let her go through the door first and put a hand at the small of her back for a moment to guide her.

If you do that, see how she reacts - if she flinches, it's not a good sign. But if she seems cool with it, that's encouraging. It's even more of an encouraging sign if SHE does that kind of thing to YOU.
posted by EmpressCallipygos at 11:08 AM on April 9, 2012 [9 favorites]

The initial stages of flirting closely resemble the initial stages of making a new friend. (Which is frustrating, because the two can be confused.) (Which is super-frustrating when you factor the existence of homosexuals into the mix...)

As the Empress points out, one major diff between "mere" friendship and flirting is physical contact... It's much more likely, and likely to be slightly prolonged, during flirting. Another is explicit eye contact: a flirter is likely to lock-on to your eyes when the two of you are talking.

An important point to remember is: you're going to fail. Going to get shot down, turned down, embarassed. It's part of the deal. It's OK. Nothing is damaged forever, IF you don't make a huge deal out of it. I have friends I asked out & got turned down by years ago; we moved on, once I realized it was only going to be friendship. Don't be afraid to try, and don't be too upset when the inevitable happens and someone says "no". Fail often, learn more - and succeed more!
posted by IAmBroom at 11:14 AM on April 9, 2012 [1 favorite]

You mentioned that this probably seems basic to most - I want to note that a lot of people of all types struggle with getting dates and interacting with women/men, and it's very normal to have to learn to do this. Some people learn younger, some people learn older. It's so normal to struggle with this - please go easy on yourself for not knowing it all yet.
posted by insectosaurus at 11:14 AM on April 9, 2012

I have a similar set of twitches from different circumstances (spent my adolescent years in the closet, paranoid that I was giving off unwanted signals, and assuming all signals were unwanted.) The way I've learned to get around those twitches is to be completely, dorkily explicit about stuff like that.

So I have literally said "Hey it totally turns me on when you sit on my lap," "I think you're cute as hell," and once used a perfectly timed eyebrow raise at a concert during Kiss Me Baby to great effect. It's not suave, but it generally seems to work, and it calms my neuroses about moving too fast/being too pushy/whatever.

I think the "just kiss her, you fool" thing works fine in theory, but if you're not both a) confident in your ability to read signals and b) confident in your ability to handle an awkward rejection, it's a pretty big leap to make. Instead, just say "Hey I think I'd like to kiss you, what do you think about that?"
posted by restless_nomad at 11:15 AM on April 9, 2012 [8 favorites]

I do not think you should just go in for a kiss without ANY welcomed physical contact beforehand. It's best to do less intrusive things first and observe whether or not they are welcome. To make this as concrete as possible:

If you sit down a little closer to her on the couch than you normally would, notice whether or not she inches away.

If you take her hand, does she pull it back, go rigid, turn the rest of her body away from you/move away? Or does she smile, turn toward you, relax?

If you stroke her hair behind her ear, does she frown, twitch, move her head away, avoid eye contact? Or does she make eye contact and smile?
posted by cairdeas at 11:17 AM on April 9, 2012 [7 favorites]

I would beg to differ that talking about what you want physically doesn't have to be awkward. I'm sort of used to negotiating those things out loud (because I'm not monogamous and there's just a lot more negotiation) but, I think it could serve you well too.

I'd do a combo of what EmpressCallipygos said (feeling out safer forms of unobtrusive touch) and something along the lines of "Hey, SpecialSomeone, I think you are really delightful, and I'm attracted to you. I'd love to make out with [or touch] [or rub your shoulders] you - how'd you feel about that?" Confidence and a sense of lightheartedness usually make that conversation go swimmingly well. Couching it in a compliment usually go a long way, and putting the "responsibility" of the feelings on yourself gives her an easy out to politely rejecting.

And I find it's more comforting to have direct rejection (which rarely ends up happening anyway) than to indefinitely mind-read confusing signals (because people have different body language too! it's not universal!).

Good luck, you sound like a winner!
posted by Betty's Table at 11:19 AM on April 9, 2012

Also, I disagree that being straightforward is always a bad idea - sure, "wanna make out?" isn't smooth, but how about,"I've really enjoyed talking with you this evening. May I take you out to dinner next week?"
posted by insectosaurus at 11:20 AM on April 9, 2012 [5 favorites]

Are you going on actual dates?

I feel like there's two pieces here:

First, the idea that self-worth is both highly contingent and consistent across milieux - ie, the idea that when you were fat and had no career you obviously had nothing going for you and didn't deserve love. That's stupid on the face of it - I've dated fat folks with nothing much going on career-wise and been extremely happy with them. And it's also lurking around in your head - because you see desirability as so precarious, you've got this huge source of nervousness and misery underneath everything else.

I'd suggest learning not to hate and despise your former self. For one thing, folks gain weight and go through career changes. Ten years from now, you might be fat and in a career slump - but even if you are, I'm sure you'll still have things to offer, dating-wise. For another, defining yourself as "I used to be this fat pathetic person but now I am great!" is just a miserable way to be, since it renders large chunks of your life and experience - the things that really do make you yourself - unacceptable, rejected, shameful.

Second, I'd suggest going on unambiguous dates. That way, you know that there's at least some attraction there. And I've always felt that "I'd really like to kiss you now" is a pretty good line, one that has worked on me in the past. On the other hand, I've always hated the unexpected random kiss or grab that I can't turn down. (There are certain instances where 'making a move' is obvious - like, you're lying in a hammock together under the stars talking idly and flirtily - but you tend to notice those things when they happen.)

Also, think of your personal style - do you really see yourself as a slickster wannabe, the kind of dude who "makes a move" on some abstraction of a woman in the hopes of, what, "getting some action" or something? Go on dates. Verbally express interest.
posted by Frowner at 11:22 AM on April 9, 2012 [26 favorites]

When in doubt humor always worked for me. "So if I've learned my dating rules correctly from cheesy romantic comedies, this is the point where I'm supposed to awkwardly lean in and kiss you goodnight." She'll either lean in herself to make it obvious that yes, that is exactly whet you are supposed to do, or she'll step back, in which case you know the answer there too.

I've been married over 20 years, so any dating advice from me should probably come with several pages of disclaimers ;)
posted by COD at 11:22 AM on April 9, 2012 [4 favorites]

The initial stages of flirting closely resemble the initial stages of making a new friend.

As a guy, couldn't disagree more. If it feels like friend making, she's probably not interested in anything more. Imagine how you would handle a woman approaching you that you are not AT ALL interested in, you'd probably keep some physical distance and avoid prolonged eye contact yet chat affably(assuming you're not an asshole). I have never had a women react to my own presence in this way and had it lead to anything. Eye contact > touching > fucking.

I'm a little autistic about this as well, so I like objectively measurable things, if you get your face really close to hers when you want to kiss her, watch her eyes. If they shift at all, pull back. Not 100% thing, but it is probably a good thing to watch out for
posted by Patbon at 11:24 AM on April 9, 2012

(Also, I am lukewarm on the 'accidental' touch - I tend to assume that it truly is accidental or platonic and get all anxious about not seeming to notice or read it the wrong way. Plus there are certain kinds of 'accidental' touches that I really dislike - I would be genuinely shocked if someone took my hand at random, for example. And I had a friend in college who would flip out on you like a ninja if you touched her head - there was some pretty bad history involved whose details I never really learned.)
posted by Frowner at 11:25 AM on April 9, 2012 [2 favorites]

Is it really just as simple as leaning over and kissing her and hoping you've read things correctly?

It's also being prepared to have misread the situation. Which is going to happen. I don't mean it may happen, I mean that in the course of dating, you're going to kiss someone who was neither prepared to, nor wanted to be kissed. And it won't be because you're Objectively Undesirable. It'll be because you misread the situation like we all do from time to time. Of all the dudes whose dating histories I know, "lack of trying" is the primary reason to have slipped up on that front. And it sucks and you have to have a little voice in the back of your head at all times rejection is a risk screaming PLAY IT COOL, MAN, PLAY IT COOL! Because fuck if you want to go from delivering an undesired kiss to Sad Panic Mode. That makes things worse.

I'm still that unfuckably fat scrub in my head, even though I haven't actually been that guy in a long time.

Put a rubber band on your wrist, or whatever you need to do, to stop shit-talking yourself in your head. Stop thinking it in the actual. Stop thinking it in the retrospective. Stop thinking it in the theoretical. If you need to be down on yourself, don't go past "I was somewhat less attractive then." That should be the absolute limit. Otherwise, that conception of you will never go away. You decide who you were as much as who you are. Instead of conceptualizing past-you as that guy, conceptualize past-you as the guy who got off his ass and started on a path that got you to where you are today.
posted by griphus at 11:28 AM on April 9, 2012 [6 favorites]

So AskMe guys, how do you know when a woman you're with would be open to your making a move? And more to the point, how do you do it? God, that's an embarrassing question to type but I'm really lost. Is it really just as simple as leaning over and kissing her and hoping you've read things correctly?

Before that, while you're out on a date, try some more casual physical interaction first-- put your arm around her shoulder or waist, hold hands, fix her hair, etc... If she's open to all of that, then dancing close, sitting next to her on the couch, and so on would be the next step. That and a glass of wine or two has been pretty much my pattern for every time I've made a move on anybody, and about half the time, they made the move on me.
posted by empath at 11:29 AM on April 9, 2012 [1 favorite]

"...'lack of trying' is the primary reason to never have slipped up on that front."

Missed an important word there.
posted by griphus at 11:33 AM on April 9, 2012

I'm working hard on not being shy anymore but I've never initiated and I'm pretty twisted up about it.

You know, paying some attention to yourself might be the ticket to get you over the remaining roughness. Get yourself some good grooming products - maybe treat yourself to a salon appointment and ask the stylist for advice. Upgrade your shaving ritual. (I bought a male friend this book and he liked it.) Make sure you aren't dressing schlumpy. Take care of yourself. Be sure to give yourself small luxuries, like a favorite liquor or clean sheets or whatever makes you feel manly. I love watching Dos Equis' The Most Interesting Man in the World commercials - figure out how to tap that inner attitude in yourself. Maybe you need some new boots or a nice jacket to throw off the lingering dregs of your self esteem issues. Something. Basically, figure out how to seduce yourself and you'll be closer to figuring out how to seduce someone else.

You really don't have to be a hardbody to be "worthy" of female attention. We love it when you're clean and you smell good and you aren't wandering around in sweats 24/7 and you are paying attention to what we might like. With the right attitude, the rest of the problem solves itself. If women are launching themselves at you, you are definitely doing something right.
posted by griselda at 11:33 AM on April 9, 2012

I sympathize, I really do. I'm a woman, and if the human population depended on me making the first move, we'd die out in a jiffy. This answer from an earlier question (don't judge it by the outcome!) sounded excellent to me, all the little ways to get comfortable with giving physical affection before "making the move."

I've also seen people advise here saying, "I really want to kiss you now," and I think that nicely walks the line between asking and just jumping in. It's declarative, but it also gives her a built-in escape, just in case.
posted by gladly at 11:33 AM on April 9, 2012 [1 favorite]

Also, btw, if a woman gives you signals that she's interested like inviting you over to her place for drinks, etc, it's a hell of a lot more likely that she's interested you that way if you've just met her recently, than it is if you've known her for a while and have already been friends... Every time i've misread signals it was from someone i had been friends with for a while.
posted by empath at 11:37 AM on April 9, 2012 [1 favorite]

Oh, that "I want to kiss you now line" should be in one of those IN CASE OF EMERGENCY: BREAK GLASS cases in your head. Only use it when you like the person so much but things are so ambiguous you're willing to sacrifice the entire romantic mood of the night just to actually kiss them. Because while it is clearly preferred by certain women to the surprise-kiss, other women (women who may be attracted to you!) may consider it a serious turn-off as it betrays a lack of sexual initiative. Again, trust your judgement to know who is whom, but from a life of dating anecdotes from my friends, that's a really dangerous (and not in the sexy way) line.
posted by griphus at 11:39 AM on April 9, 2012 [8 favorites]

I've always been a big fan of the, "I'd really like to kiss you," thing. It does two very important things. As noted, it's declarative, but gives her options. If it really is kissy time, then it doesn't much matter what you say as long as you make your intentions known. "ME KISS GIRL NOW" everybody smiles, kisses.

The second thing is arguably much more important. The girls who DID want you to kiss them, but say something like, "You can't ask. Now you ruined it." This is a symptom of preference for dramatic games.

Let me also add an advanced technique that I myself am almost never calm/confident enough to use. When you touch her arm (or wherever) while making eye contact, note whether her pupils dilate. If they do, and she's not regressing into fight or flight response, she's attracted to you and there aren't many more than two ways about it.
posted by cmoj at 11:43 AM on April 9, 2012 [3 favorites]

have little difficulty arranging private time with women that interest me.

By this, do you mean that you ask them out on dates that are obviously dates? As in, "I'd really like to take you out on a date. Are you free for dinner Friday?" or "Can I take you out to dinner this weekend?" Because if someone asked me out on a date, and I was interested enough to say yes, and on that date we were having such a nice time together that we went back to my place or his, I'd pretty much expect one of us to be making a move. In that case, yeah, just lean over and kiss her.

On the other hand, if you're framing these situations as "let's hang out," then I think you're setting yourself up for awkwardness. I mean, yeah, the woman you're interested in probably agreed to "hang out" because she's interested in you, but it's just a much more ambiguous situation.

If you lack self-confidence to gauge these situations, it's better to be explicit before they happen--"let's go on a date! I like you!"--because the woman will say yes or no based (generally) on whether she's open to pursuing a romantic relationship with you. If you leave things more vague and ambiguous, there's greater risk that she's accepting your invitation because you seem like a fun new friend--she might even be thinking, "Well, he's not asking me out on a date-date... I'd seem pretty vain if I said, 'OK, but you know this isn't a date, right?'"
posted by Meg_Murry at 11:47 AM on April 9, 2012 [5 favorites]

Do not hide the fact that you are attracted to her. A lot of shy guys seem to feel that they need to pretend to be asexual or at least not thinking about anything like that, but assuming the context is right (a date, etc.) then it's appropriate to let it show. When you compliment her, don't make it sound like a formality, make it sound like you are genuinely affected by how she looks.

If you're both into each other, there should be smiling and eye contact and a general warm feeling. You can gently, in the flow of conversation, touch her leg or back or hand. (Again, I'm talking about an appropriate context like a date, not hitting on some woman who doesn't know you in an inappropriate place.) If she does not quickly pull away, you can gradually escalate the physical contact. Let your palm rest on her leg. Take her hand in yours. Brush her cheek with the backs of your fingers. Then lean in partway for a kiss and give her a chance to avoid it. Then kiss her.

You could probably learn something from the "pick up" stuff that's out there on the internet. Avoid the misogyny and manipulation, but they break down a lot of the stuff people do unconsciously so that it makes sense.
posted by callmejay at 11:47 AM on April 9, 2012 [4 favorites]

It'll seem like the moment is right but oh christ, what if it isn't?

Um yeah, so what if it isn't? You'll get a "no" from her in some form or another - in words or in actions. And those words or actions will tell you a little more about what to do after that - apologize and go away, apologize and see her next week, giggle about it, try again another time, try again a different way, etc.

What I'm trying to say is that it won't be the end of the world. Yes, you might feel embarrassed or sheepish if your advance isn't welcomed. And that's okay. You'll learn something from the attempt itself and be just a little more ready for the next time, whether it's with the same woman or the next.
posted by agentmitten at 11:48 AM on April 9, 2012 [1 favorite]

Well, here's the pep talk about being fat from someone who is fat:

You had some serious things holding you back and you STILL had women initiating romance. Not just putting up with it, initiating things and trying to get with you. That's impressive as hell.

Anyway, in terms of kissing...if you fuck it up, it's not that big of a deal. Plenty of guys have kissed me and I've been all BLAH NO EW but as long as they don't get pissed off that I don't want to kiss them, it doesn't make me think less of them as people or as friends. I even have friends with whom my reaction to them trying to kiss me is an inside joke. It'll be okay, I promise.
posted by the young rope-rider at 11:54 AM on April 9, 2012 [2 favorites]

tl;dr version: booze.

Not totally proud of this, but I've had enough situations in my life where one too many glasses of wine/beers resulted in an encounter that could otherwise have required weeks or months of further mutual circling and intention-sniffing. Yeah its not the greatest thing, you can make bad decisions and you might have a hangover, but I was still thankful that it paved the way for getting the awkward stuff done with that much sooner, so we can get on to the good stuff.

Obviously, this may be untenable for you and/or the woman for all sorts of reasons.
posted by tempythethird at 11:58 AM on April 9, 2012 [1 favorite]

Yeah I hate to have to come down against the whole asking to kiss thing, because I acknowledge it seems like a great option...but I don't have one female friend who feels positively about this. Not one. I have friends for whom it's not horrible but ruins the mood slightly, and friends who positively loathe it. Those are the only two opinions I've ever heard expressed: Meh, or HATE. As far as the declarative "I really want to kiss you right now," my friends prefer it to being asked (as do I), but none of us particularly like it. That said, it's not likely to hurt your chances if we're into you.

I'm going to echo the physical touch advice. It absolutely must not be "accidental" touch, though. I would spend the second half of a date that's been going well upping the ante on every successive touch. By the time you kiss me, your arm is likely to be around my shoulder, or we are likely to have spent a good portion of the date sitting so close to each other that our thighs and shoulders are touching.

And one last thing. If I come over to your place after a date, I WANT YOU TO MAKE A MOVE. A woman who is not interested in even a goodnight kiss will not go inside your place at the end of a date. That would just I cannot imagine anyone doing that. It certainly doesn't necessarily indicate we're up for sex, but if we're hanging out at your place and it's explicitly a date? Yeah, a kiss is downright expected.

Er, and one last, last thing. callmejay just made a very good point. Do NOT hide that you are attracted to her. If I'm on a date with someone, quite frankly, I don't want him acting like he's just getting to know a new friend. For Pete's sake, feel free to imagine kissing me! There's an energy shift (that I NEED to feel from a date for me to want to kiss them, by the by, though that's a personal preference) that occurs when a person is thinking about another person in a sexual way. Really, every so often, spend a couple seconds fantasizing about what you'd like to do to your date. I swear that kind of thing changes the vibe of the date. In a sexy way.
posted by JuliaIglesias at 11:58 AM on April 9, 2012 [20 favorites]

Sometimes awkwardness isn't necessarily a bad thing--it can be sweet, or funny, or endearing. The first time I kissed the first dude I ever seriously dated (he was 27 at the time, so this wasn't high school awkwardness) was immediately after he said "I think you're fucking awesome", leaned over, and kissed me on the cheek. We'd been watching a movie on the couch together, and it was sort of unexpected, and ultimately, one of my fondest memories of him, because it *was* sort of awkward, in an adorable way. In other words, the awkwardness you feel can work to your advantage! The first time you "make a move" on someone doesn't have to be this perfectly planned, "suave" thing. I would go as far as saying that it feels a lot more genuine, and fun, if it isn't.
posted by dysh at 12:23 PM on April 9, 2012 [3 favorites]

The trouble I'm having is that my assumption of my own undesirability seems to have outlived the material causes for it.

That's because there were no material causes for it. Big guys get love too. You are dealing with something else.

I suggest Intimate Connections
posted by Ironmouth at 12:40 PM on April 9, 2012 [3 favorites]

My problem is that this all falls apart in private, that I've spent years believing no woman could want me and all that old fat, broke slob nervousness still haunts me when I start thinking I'd like to get closer to a woman I'm alone with. I struggle with this even when I've got the strong suspicion that she wouldn't mind me making a move.

---------> Everyone has insecurities. With what you're saying you could easily swap out "old, fat, broke, slob" for whatever personal insecurity that each and every one of us has - and we all have them. It's what makes us human beings. There was something someone said on here awhile ago that I kind of stuck in the back of my mind before I got into a committed relationship: people have all different preferences and there's no one "type". Some people prefer blondes over brunettes just as some people may prefer cats over dogs, the color green over red, or athletic over skinny. It's all personal preference and it holds true to the types of people we are attracted to and what makes us attractive to others.

Your story resonates with me though because you sound so much like my boyfriend. I met my super-awesome boyfriend last summer and we were just friends until the fall. We met through a sports club, and honestly, I didn't think anything of it at the time because I was too busy going on crappy internet dates all summer and he wasn't my type (or whatever I thought was my type at the time). He had lost over 100 pounds with diet and exercise alone in the year prior and was probably feeling much of what you're feeling at the time (and I know he still struggles with it, which I would think is to be expected).

Because I was so distracted at the time by other dating drama in my life, unknowingly he was very gently pursuing me. What he now considers our first "date" I didn't think anything of it at the time - we happened to be out having dinner at a pub together randomly after doing some volunteer work, had dinner and a few drinks and then went our seperate ways - no hugs goodbye or anything like that. He's super outgoing in groups and in public, but I think much like you, he struggles with the alone time.

It all came together for us when after that random dinner, he asked me if I wanted to come over to his place for dinner the following week. I said yes and brought wine and just kind of shrugged. He cooked a fabulous dinner and the two of us found ourselves chatting away. I realized it was getting a little late so I thanked him and he walked me out to my car - and then just leaned over and planted one on me. I had been totally aloof about him until that moment and you know what? I probably would have continued to be aloof but he stopped me dead in my tracks. Fast forward about 6-7 months and we're ridiculously happy together.

Just do it - seriously. You may run into some rejections, but if you have said strong suspicion (as I think my BF did) just go for it - you might be pleasantly surprised. YMMV.

You can't learn to dance without taking a few missteps.
posted by floweredfish at 12:41 PM on April 9, 2012 [1 favorite]

I'm a woman, and I absolutely love it when a person asks, "Can I kiss you?" It has been used on me twice recently, once to our extraordinary mutual delight, once not to such immediate delight but it's gotten me thinking. Both of the men in question have several-many gorgeous lovers, and so I have to say it's not just me who's loving their approach.

It shouldn't be coming out of the blue -- the first fellow already had a verbal statement of interest on my part, as well as low level welcomed physical contact. The second I was snuggling closely and chatting with, and the fact that he asked instead of just "going for it" meant for me that I continue to be comfortable snuggling with him.
posted by endless_forms at 12:42 PM on April 9, 2012 [2 favorites]

I'm a lady and I've asked "Can I kiss you?" to great effect. I've also said yes when a guy asked me something similar. I think for those of us who are awkward about dating, like me, it can be easier that way. In fact, I might even be put off by someone going in for a kiss without asking since I am not that forward.

By the way, congrats on doing so much to improve your life already; I'm impressed!
posted by mlle valentine at 12:55 PM on April 9, 2012

I've said it before, and I'll say it again... My personal mind-hack for this is to meditate a little on the fact that what I'm doing is trying to send a very clear signal to the other person that I want something that's going to make her life better.

It also takes a wee bit of self-centered self-talk: "I am *NOT* going to go home and regret not making a move on you, and if that means you're going to go home and feel awkward about it, so be it. But I'll be cool about it, and if this is the worst thing that happens to you this week, you've got it pretty sweet." (Don't say this out loud.)

It's kind of due to the nature of the game, that it really may be a choice between her feeling awkward and you going home and feeling like a bit of a whuss (assuming she's not interested), but I think you're better off coming to terms with the fact that this is going to happen to the occasional woman than learning to get her signals 100% of the time.

Also, I like, "Hey, come here for a sec" with a little smile to get things moving.
posted by alphanerd at 1:27 PM on April 9, 2012 [6 favorites]

it wasn't supposed to last longer than the weight did

Unfortunately, psychological effects often outlast their causes. This is why so many people are in therapy to clean up shit from their childhoods and adolescence. Not to say that you can't overcome this -- just don't be overly hard on yourself. It sounds like you're doing fine, and this will come.

I used to suck at flirting and now I suck less. Few people would say they are really good at it; all we can aspire to is sucking less, so don't worry if you feel like you're not where you want to be. Myself, I'm not sure what happened to me except that I gradually got more comfortable in my own skin and was able to relax. But here are three specific things I've learned that might help.

1. A potentially romantic situation is sort of like building a fire. Most conversations hum along like a tiny little fire. Every phrase you say is like a log on the fire that makes it heat up. You can't drop a big tree trunk right on a little flame or it will smother it out. But neither can you just throw on one little twig after another and hope it will suddenly jump to life. Eventually you have to take a chance and escalate, and you have to do so in appropriate increments -- neither twigs nor tree trunks -- until your partner notices it and responds. Your partner will either reciprocate, or snuff it out.

2. It is awkward when intentions are misread, but awkwardness can be defused if both parties have a plausible way of pretending that the awkward thing never happened. You might say something which was intended to be flirty; she might defuse it; you will both know that she shut you down, but if your statement was slightly ambiguous you can carry on as if she misinterpreted it, and she can carry on as if you didn't mean it that way. This is what I meant by increments and it is what flirting is all about. Lingering eye contact, a brief touch on the arm, a joke with a slight double entendre, a suggestion that you go outside for a walk together, all are subtle ways of stoking the fire, and if you do enough of them you'll notice that she is either joining you in stoking it, or she is snuffing it out. (Your instincts are correct, by the way; "wanna make out" is dropping a giant tree trunk on your little conversational fire. It will sit there demanding to be acknowledged, but the odds of it spontaneously bursting into flame are low.)

3. There were times when I wanted to kiss someone and was *almost* sure she would be into it, but couldn't figure out exactly how to go for it and still a little scared about the almost. If you feel the possibility of a 'moment', try brushing her hair across her forehead and caressing the side of her face. It is an unmistakably intimate gesture, but one which is I believe is a little less forward than a kiss and easier for her to back away from elegantly. It's kind of like asking 'can I kiss you' without words, and if she wants to say no she can answer without words simply by turning away. You will know right away what she is feeling, and if she is looking into your eyes, smiling, and/or blushing, well, kiss her!

Good luck. And congrats on the success you've had getting things together so far. It sounds like you've worked really hard and you will make a great partner for someone.
posted by PercussivePaul at 1:37 PM on April 9, 2012 [10 favorites]

tl;rd but now that I'm an old guy, here's my advice:

Just grab her and try to kiss her.

Don't think about it, and don't stall. Just make the pass.
If she's not ready, you'll get the message.

Practice make perfect, try again, when you next get the opportunity, you got nothing to lose, timing is everything, etc.etc. Thing is, even failing at this makes you stronger -- but if you do nothing, you lose.
posted by Rash at 1:40 PM on April 9, 2012 [1 favorite]

step one: like yourself.
Step two: love yourself.
Step three: Have courage, confidence, and, well, balls :)

Realize that no matter how bad you look, someone will want to have sex with you. Realize that no matter how awkward you are, someone will want to date you. Mix in my three steps, start looking for the right people to date, and you will find someone.

Yes, it can be hard to read signals. Maybe go to a bar and watch other people flirting, so you can observe in a low-pressure situation. But look at how the flow of the date went. A lot of eye contact and smiling? Good sign. Easy conversation? Good sign. Looking down a lot, short answers, and little smiles? Either a bad sign or terribly shy girl. If she touches you? Probably a great sign.

My GF seconds the step three. She keeps pointing out to my single guy friends that its not their looks or (extreme) nerdyness, its the attitude. The schlubbyness. The Charlie Brown attitude. To quote different friends "emotion follows motion. Also, fake it till you make it" And experiment lots. Do not worry about fail. Do, or do not.

Youve got good stuff going for you. Tell yourself that. Literally, in the mirror if need be.
posted by Jacen at 2:55 PM on April 9, 2012

Don't be afraid to put out the signals you're looking for, if you're interested. When people are interested in each other, they respond to each other (sometimes consciously, sometimes not) by aping and heightening each other's gestures and expressions and postures and whatnot. So if (say) extended eye contact, leaning towards each other during converstation, and close physical proximity are signs of interest you might look for, then by all means make extended eye contact, lean towards her during conversation, and keep your physical proximity close. If she does the same thing, things should heighten pretty quickly, and if she shies away, then it'll be really obvious to you that she's not responding.

tl;dr: don't show restraint and then expect overt signs of interest from others; show overt signs of interest and see if they're returned, instead.

Also, I've always been tall and thin, and now I'm successful as well, but I have never been able to shed the sense that nobody could possibly be interested in me, even though I have a track record that suggests otherwise. Sometimes we have hangups in our self-esteem that we can't identify the root cause of, or shake entirely, but you'll do well to push through it knowing that yes, some won't be interested, but some will, and you'll never know unless you start sorting through both types of people.
posted by davejay at 4:24 PM on April 9, 2012 [1 favorite]

Maybe I'm wrong, but it seems like you're asking for the mechanics of what exactly to do in the moment, and people are giving you advice on how to be confident in general. So, I'm going to tell you the ways in which I feel the least awkward when a guy makes a move on me.

Personally, I feel like a first kiss is way less awkward when two people are standing up instead of sitting, say, on a couch or whatever. Because the moment right before it happens is the most excruciatingly awkward part, and when you're standing it can happen a lot faster, and be backed out of a lot more easily. If I'm sitting on a couch next to a guy and I think he's going to make a move and I'm not sure if I want that, what do I do? Get up and move? Awkward. But if we're both standing and he gets too close I can just casually step further away. If I'm into it, I might step a little closer, put my hands on his shoulders, whatever.

So my advice for places to do this . . . I guess it depends on where you're seeing these women. Honestly, I recommend going out to a place that involves at least some drinking. If you are the type who would play pool, I have found this is a great way to lead up to it. There's drinking, a little bit of competition and heckling, and you're basically walking in circles around each other. Tons of sexual tension and a perfect opportunity for a congratulatory kiss when one of you wins (or consolation for the loser.) You can start with small physical contact like, I don't know, high fives. Be creative. You can offer your hand for a congratulatory high five/ handshake and then hold onto her hand for a moment. If she pulls it away quickly, wait. If she lets you hang on to her hand, try pulling her in a little closer to you. Look in her eyes. (That's always the key- be close, face to face, make eye contact and if she reciprocates the prolonged eye contact while you're making physical contact, such and holding her hand, it's a go.) Smile, lean in and kiss her.

Pool not your thing? Okay. How about when you're on a date at a bar? I recommend sitting AT the bar next to each other, rather than at a table across from each other. It will probably be loud, so it's only natural that you'll have to practically be on top of each other to hear anything. It's also really easy to put a hand on the leg- be opportunistic though. Don't just do it randomly, save it for when she says something hilarious/ endearing/ sexy. If the sparks are flying and you don't mind PDA, you can kiss her at the bar. In fact, you can even use this as an excuse to test the waters- once I was in the middle of such a date and the guy says to me, "I really want to kiss you right now but we're in the middle of this crowded bar and I don't want you to be embarrassed." Then it's up to her to either say "Fuck it, let's make out a little anyway" (the option I chose!) Or, "hey let's leave then." Or she might just giggle and look away and then maybe you know she's not so into it.

Other options: when you're leaving the bar/ restaurant/ whatever, grab her arm or hand. If she is into it, you're golden. After walking like that and flirting for a minute or two (I guess this depends where you live, I live in a city so it's totally natural to be walking six blocks on somebody's arm, probably won't be so slick if you're just walking to a parking lot)- anyway, just slow down, pull her closer with the hand/arm you're already holding, grab her with the other hand, look in her eyes. If she's going along with it, then now's the time to kiss her. This is much better walking down a city street, though, so if you don't live in a big city at least be in a cool downtown area if you can swing it. Anyway, you can't make out on a public street forever, so do that just a little and then stop and be like "So . . . should we continue this date at your/ my place?"

Ok, so let's say none of that worked and you end up back at her/ your place but haven't made a move yet. If you've already been drinking, I'd make the move sooner rather than later, and again- standing up. A perfect place is in the kitchen, as drinks are being poured. Take her drink gently out of her hand, set it on the counter, lean in and kiss her. If you haven't had any drinks yet and need some courage, then have a couple and then do this move when you guys get up to pour the third round of drinks. In any case, my advice is the same- some sort of prolonged physical contact (your hand on her shoulder/ arm/ hand)- if she lets it stay there, look into her eyes. If she isn't looking back into your eyes, don't do it. If she is, then it's go time. Look at her mouth, back at her eyes, lean in and by that point hopefully she'll be going for it too and you'll meet in the middle!

Lastly, just an unsolicited bit of advice regarding the previously-fat thing. It's not a big deal unless you make it one, which sadly, some guys do. I've dated guys in your shoes and often they seem to really be focused on it- talk all the time about exercising, food, etc. It's boring when women do it, why would it be any different for a man? I'd throw it out there exactly one time: "I used to be bigger, I feel pretty great now but every now and then I'm still a bit self conscious about it so that's why I act shy sometimes." That's it. Once she knows, she won't forget it. If she doesn't like it, she'll fuck off. If she doesn't care, she'll stick around. Good luck to you!
posted by Argyle_Sock_Puppet at 4:28 PM on April 9, 2012 [8 favorites]

Join okcupid. This has really helped me - it eliminates the confusion and guesswork that come with meeting random people in bars because it puts you in touch with people who are 1) single and 2) interested in you.

You'll go on dates with women who are meeting you specifically because they believe you may be a romantic possibility. Don't take it too seriously, just write a good profile, put up some good pictures and make a point of writing to every single woman you think you *might* want to spend time with. (No form letters, but short is fine). Some of them will write back. This will get you some dates, and if you like someone you can suggest that you meet again - which should be easy because you've already gotten the first date out of the way, right? - and if she says yes to a second date then kissing her at the end of it is a pretty logical move.

As other people have already said, the physical cues are important - watch for that.

And for what it's worth ... I dated a bigger guy a while back. I thought he was wonderful and I'm still sorry things didn't work out between us. So keep in mind that you are probably more worried about your body than your dates are. Your dates? Are worried about *their* bodies, if anything.
posted by bunderful at 5:23 PM on April 9, 2012

Also - embrace bad dates as part of the process. The bad dates are usually not really bad dates, they are just not the date you were hoping for. They can still be funny, you can still get to hear someone's story and learn something new from them. And a long series of "bad" dates can still be good for your confidence.
posted by bunderful at 5:25 PM on April 9, 2012 [1 favorite]

Join okcupid. This has really helped me - it eliminates the confusion and guesswork that come with meeting random people in bars because it puts you in touch with people who are 1) single and 2) interested in you.

Honestly, you don't even need to contact people on there first. Just throw up a half decent profile, and you will get messages-- guys get less than women, but you will get them. And if a woman contacts you first on there, it's about a 90% chance you're going to hook up with them unless you're a complete disaster.
posted by empath at 6:14 PM on April 9, 2012

I've spent years believing no woman could want me

Try to work on your negative self-talk. You said yourself that women hit on you in the past, so this is in fact not even true. There must have always been something attractive about you. Not every guy gets hit on by women, you know.

Good luck!
posted by bearette at 6:37 PM on April 9, 2012 [1 favorite]

Yeah, objective physical attractiveness will only get you so far. It might be easier to get first dates, but beynd that, it is all about being intellectually and emotionally attractive.

(The Spencer family advice from "Psych": first you treat a woman like a person, then a princess, then a greek goddess, then a person again. The word choice of "a person" is a little weird, but the point I think is to NOT treat people you are romantically interested in like a crappy salesman treats a mark: don't keep your eye on the prize, because that's creepy and manipulative. Rather, be normal. Joke around, don't over censor, be comfortable in the situation. If it leads somewhere, great, if it doesn't, well, you had a nice time with a new friend.)

I'm not great at "making the move" either. But one thing I know is that we are instinctively wired up to do the mating dance. As other people have said, it is the casual touching and the escalating physical closeness. Each person has their role to play, and each should be pushing the envelope a little bit. In a perfect world, anyway. When you are out with someone who is a bit more reserved or shy, it is very hard to tell. If the person agrees to another date, or wants to change venues with you "hey that was good coffee, do you want to grab a drink next door?", things are looking good.

Other things I've learned: if you met on a dating site, if the conversation turns to "so, have you dated much on $DATINGSITE?" chances are the date isn't going as well as you thought. The later in the conversation that happens, the more likely this is to be true. Could just be confirmation bias on my part, but the rule has held true for me.

And there is nothing wrong with being a little shy or reserved. There is nothing wrong with a little anticipation. Even if a first date felt a little awkward, ask them out again. You'll get better signals the second time.

And finally, there is nothing wrong with using a "line" if you do it right. If you are at that awkward spot where it seems like maybe someone ought to make a move, just ask a silly question where the the question and the answer will be a good indicator of the other person's level of interest. Like, "hey, want to go over there?" pointing to a quieter part of the bar, or "so, can I drive you to your car?" or "do you want to come upstairs and see the new blender I bought?" Because they are pretty silly suggestions, and if you say them with the same tone as if you were saying "do you want to make out?", someone who wants to actually make out will probably agree. (It usually does have to be a real thing you can do. If it is absurd, like you really don't have a blender to show off, it CAN seem creepy.) But anyway, do that thing, and make the move.
posted by gjc at 6:52 PM on April 9, 2012 [1 favorite]

Honestly, you don't even need to contact people on there first. Just throw up a half decent profile, and you will get messages-- guys get less than women, but you will get them. And if a woman contacts you first on there, it's about a 90% chance you're going to hook up with them unless you're a complete disaster.

I just want to chime in to say that this is not the case. First off, OKCupid is designed so that when you are not actively using the site (ie, browsing profiles, sending messages), you don't show up as much on peoples' homepages or in search results. When I was using it, I'd sort of go on messaging binges, then stop for awhile as my prior set of messages sorted themselves out. When mid-binge, I'd regularly get messages from women, when not, I got them far less often. When I didn't log into the site for a few weeks I got, literally, one message.

Second, maybe I'm a complete disaster, but I went out with several women who messaged me first and did not hook up with 90% of them. With online dating, it helps to think of the first meeting as a more-or-less blank slate - your prior, internet-based, interactions are of minimal importance. They can probably provide some conversational fodder, but that's about it. The online, pre-meeting, interactions, in my experience, literally indicated nothing about how the actual dates would go.

I quite like OKCupid, because it makes it so easy to get dates, which increases your confidence - not because you're getting dates (which, let's face it, is not very hard on the internet provided you can write reasonably well and have a few good photos), but because it decreases the marginal importance of each date. You aren't agonizing over every little thing that went wrong, because you can just move on to the next one. But if you're going to do it, you should do it right. Message people regularly, put some thought into it, view everything through the lens of maximizing the odds of in-person meetings.

Anyway, I just wanted to say this in case you end up going on a date with a woman that messaged you online and don't make out with her and end up thinking you are a complete disaster. You are not.
posted by breakin' the law at 7:48 PM on April 9, 2012 [1 favorite]

Data point, my partner asked if he could kiss me on our second date, and it was the most awkward thing (he is not exactly the most suave dude on the planet) but it didn't scare me off either. AND I declined! AND I continued to hang out with him, and eventually kiss him, and move in with him, and have a child with him. My point being, you may not be super slick right away in the make-a-move department, but you should still make an effort. It won't be the end of the world, even if it is awkward.
posted by celtalitha at 9:15 PM on April 9, 2012

If a guy asked if we could make out, that would be weird. (Unless they were one of those really funny quirky people who could make it cute). But I love it when guys ask if they may kiss me, as long as they seem confident rather than freaked out when they ask. The best kiss of my life happened that way. Just don't ask before you do everything. That's weird. (May I touch your left breast now? Now may I rub your innner thigh? Is it ok with you if I nibble on your neck?... Ugh).
posted by windykites at 9:25 PM on April 9, 2012

Also, I'm seeing some people talking about using eye contact levels as a cue. I wouldn't advise making your decision solely on that, just because I'm really shy with men I'm interested in, and it's really hard for me to make eye contact with guys I like. I think there are other shy women who feel the same way.
posted by windykites at 9:37 PM on April 9, 2012

I've been told that outright asking is a pretty clumsy thing to do and yeah, I don't see how a guy just asks "want to make out?" without it being weird.

Lots of other people have already said this, but just to add a small data point... Asking can be sexy, cute, endearing, and it can totally kick things up a notch in the romantic energy department, but most important of all, when you ask, you are no longer guessing. Being open and clear about your intentions with someone that you're interested in saves a lot of time and stress. And as a super shy chick who hasn't always found it incredibly easy to maintain eye contact and all the flirty little touches that everyone else is saying to look out for (even when I've been crushing hard on someone), I appreciate directness that I can then respond honestly to. (And have also tried hard to do my share of the asking if the other party seems a bit shy/awkward.)

You're already aware that some ladies are into being asked while others aren't, and you'll never be able to know beforehand which is which, but rather than just leaning in (or worse, grabbing her), you can use direct declarations and requests as a way of making physical intimacy happen relatively quickly without ambiguity. And if you ask and she declines, then at least you have the choice of having a conversation about whether she's just not that into you, or whether she's not sure yet, or whether she just likes to take things slowly.

I hope you logically also realise that fat dudes get plenty of love, in spite and because of size. Kudos for taking charge of your life and making the physical changes that you felt were necessary, but as you yourself have pointed out, the underlying emotional issue was there before and after the weight loss. It may sound like going a bit overboard, but have you thought about a couple of counseling sessions to try to work through what exactly you think was/is undesirable about you? It's possible that having a couple of hot make out sessions/sex with some ladies will make a huge difference to your body image, but if not, it might help to talk this through with someone.
posted by catch as catch can at 2:48 AM on April 10, 2012 [1 favorite]

I just read the SIRC guide to flirting and it is AMAZING at deconstructing how people use body language other signals to talk to each other. I'd particular recommend the section on touch w.r.t. steps to figuring out of someone wants to make out.

I have had some nonzero success with asking people if i can kiss them, but I am a generally speaking a super awkward nerd. I still have an email in my drafts saying "it was SO AWKWARD I AM SO AWKWARD IT WAS HORRIFYING". He still made out with me, though. I maintain that my awkwardness is endearing.
posted by oranger at 5:00 AM on April 10, 2012 [2 favorites]

For another, defining yourself as "I used to be this fat pathetic person but now I am great!" is just a miserable way to be, since it renders large chunks of your life and experience - the things that really do make you yourself - unacceptable, rejected, shameful.

I just want to say, as someone who's been up and down and up and down with this stuff myself, this is SUPER smart, I've never heard it put quite this way, and I'm taking it with me. Well said.
posted by Linda_Holmes at 1:02 PM on April 10, 2012

A few things:
  1. Much good advice here about in terms of giving body-language cues and responses. You're learning to have a kind of conversation; it has well-defined kinds of questions and answers. Once you're familiar with them they will be as clear as glass.
  2. If you're at the point where you're mostly in private, physically close together, and she's looking at you expectantly, you're probably a-ok. Worst case you misread. See below.
  3. Fat jobless dudes captured the attention of more than one woman I was very into. Don't beat your past self up. Just work on un-convincing your present self of the negative self-image.
  4. Seconding "first kiss a bit easier when standing up". Not essential, but helpful.

oh christ, what if it isn't

Then you have an awkward moment. Happens all the time. Happened with my then-future wife. Even if you "speak the language" fluently, you can mis-step. Happens when speaking English too, right? You sometimes say the wrong thing. So you fix it by apologizing briefly ("gosh, that was awkward, sorry") and changing the topic, backing off. If it was a clear rejection, wrap up the date at the next reasonable juncture and go home. Don't make a big deal of it; people make mistakes and/or get rejected all the time. A mistake is made worse by a dramatic reaction, and a rejection is just the price you pay for taking risks. Promise yourself it's better to try and fail than not try and feel helpless. Trust me, it is.
posted by ead at 10:28 AM on April 14, 2012

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