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Overcoming shyness in dating
May 19, 2010 8:42 AM   Subscribe

Can't make a move... should I just talk to her about it?

I'm a guy in my early forties, newly single after many years of marriage. I have very little dating experience, and suffer from crippling shyness and lack of confidence. Despite this, I have managed to do a little bit of dating, and I think my confidence is improving in the sense that I feel pretty comfortable around women and don't have too much trouble getting into a conversation.

The problem is, even on a date, when I think I'm picking up encouraging body language or verbal clues from a woman, I absolutely cannot make the first move. It feels like I'm somehow "crossing the line", and that any non-platonic gestures or advances would be unwelcome, always, no matter what. Intellectually, I realize this is ridiculous, but emotionally, that's the brick wall I keep running into.

I've been seeing a woman about once a week for a little over a month, and we always have a great time together... the conversation flows naturally, we enjoy each other's company, and I'm pretty sure she's at least a little interested. And yet, everytime we get together, nothing physical happens, and I go home feeling like a sad, pathetic loser. I just wish she would give me some kind of sign, or maybe a stronger sign, that it's OK to move to the next level. So, my question is... should I try to talk to her about this somehow, or would that "kill the romance"? Of course, this particular case might be a lost cause at this point, but I'd appreciate any ideas on how a shy-but-interested guy can communicate his interest... or learn how to fearlessly reciprocate the interest he's receiving.
posted by anonymous to Human Relations (46 answers total) 8 users marked this as a favorite
 
"I'd like to kiss you now."
posted by 256 at 8:44 AM on May 19, 2010 [4 favorites]


Next time you have a quiet moment, shift your body a little closer to her and put your hand on her hand and look her in the eye. Don't stare, just let your gaze linger over her face.

This should get a little heat flowing. If it's not enough, you're just going to have to do like 256 said and say something to her. "I'd like to kiss you now" indeed. Or perhaps, "Would it be all right if I kissed you?"
posted by Night_owl at 8:50 AM on May 19, 2010


Touch her arm a couple of times in conversation, maybe try touching her hand. Bring up topics relating to romance and relationships, discuss things you're passionate about. Look into her eyes for a little bit too long. For the kiss, either just go for it, or give a quick warning like "I can't help myself, I have to kiss you." Don't ask.
You have to push this a little bit.
posted by smitt at 8:52 AM on May 19, 2010


Hold her hand, watch her nonverbal response. Then maybe stroke her hand gently with your thumb, if it feels natural and you don't detect any aversion from her. Then kiss her hand. You're working your way up to The Kiss and there's no rush. You may get there in one day or it may happen over the course of several dates. The most important thing is that you gauge your pace on her responsiveness.
posted by The Winsome Parker Lewis at 8:53 AM on May 19, 2010


Maybe I'm the only one, because 256's idea gets suggested around here a lot, but I absolutely hate it when a guy asks if he can kiss me, or announces that he wants to. It totally kills the romance, in my book.

That said, it's not like you have to dart in quickly and hope you don't get slapped. You can move your face closer to hers as you're talking, and if she doesn't pull away, keep going. Maintain eye contact and normal mouth position until the very last second. You don't want to have your eyes closed from a foot away, or your mouth all agape like you're going to eat her. You're just talking, smiling, flirting, and then hey, whaddya know, your lips brush. She knows it's coming, you know it's coming, but the anticipation is fun. And it gives her an easy, polite way out through body language (leaning away) without her having to respond "No thanks" to a verbal announcement of your intentions.
posted by vytae at 8:54 AM on May 19, 2010 [15 favorites]


Maybe I'm the only one, because 256's idea gets suggested around here a lot, but I absolutely hate it when a guy asks if he can kiss me, or announces that he wants to. It totally kills the romance, in my book.

Really? I do find that surprising. I agree that a whole "Let's have a discussion about whether or not we're ready to be physical" is going to put a damper on the mood. But I've definitely used minor variations on the line I suggested when I was about to kiss someone for the first time. It's not said as part of dispassionate conversation:

"Are you thinking of getting the red or white wine with this?"

"I'd like to kiss you now."

But rather, at an early stage of exactly the kiss approach you describe. I've also done it just as you say, but the OP says that he has difficulty reading body language for consent, so he's likely to misinterpret any small thing as a turning away. I've never known anyone to be taken aback or shocked out of the mood by a gentle "I'd like to kiss you now" while leaning in and maintaining eye contact.
posted by 256 at 9:02 AM on May 19, 2010 [2 favorites]


I've never known anyone to be taken aback or shocked out of the mood by a gentle "I'd like to kiss you now" while leaning in and maintaining eye contact.

FWIW, I'd be totally grossed out by that.
posted by runningwithscissors at 9:04 AM on May 19, 2010 [12 favorites]


I think there's a fine line between flirting like an Apple IIe program and being a nasty, grabby jerk. I would suggest saying genuine, nice things like "You look great tonight" or whatever then touch her harm or hand and see how she reacts. Plus with little stuff like that I am dubious any major drama would happen even if she reacts badly. Yes, it will hurt for you but it's not like she's gonna dump her glass of water on you for an arm touch. If this happens, see the "it's not me it's the other person" threads, learn and move on. Bon courage!
posted by ShadePlant at 9:06 AM on May 19, 2010


256's suggestion reminds me of one of my favorite Woody Allen scenes ever. I have no idea if it will work, unfortunately. Being witty instead of just saying "I'd like to kiss you now" helps.

If you're afraid of rejection, don't be. You think it is unwelcome when, in reality, you haven't the faintest. Concentrate on that. You know you don't know if it is welcome, but the fact that it is inherently not is in your head and only in your head. Until you find out. Now, you're a guy. We're (usually) expected to initiate the first kiss which also means that plenty of women, especially in your cohort, have been undesirably kissed and know how to make it clear that it was undesired but it's really quite okay. As long as you're not a dick about it (you don't sound like the type) or prostrate yourself with apologies (you might do this. Don't.) Just be cool.
posted by griphus at 9:10 AM on May 19, 2010


I'm with the folks that think it perfectly ok to Ask if it's ok to kiss her, especially if you do it while leaning in, making it seem like a Really Fun idea for you right then. But I also wanted to point out that she keeps going on dates with you, and you guys have fun? That's a pretty great sign that she's in to you! Go ahead with that kiss sooner rather than later.
posted by ldthomps at 9:17 AM on May 19, 2010


Our findings from the above are that "I'd like to kiss you now" may work well. Or, it might not.

The conclusion I would suggest is that you should do whatever it is you are longing to do - whether that is to lean in for the kiss spontaneously, or say something romantic like the above to introduce the idea, or just, as you say, talk to her about it... when you sense that feeling welling up inside you when you're with her, DO IT!

Sod the consequenses :)
posted by greenish at 9:19 AM on May 19, 2010 [1 favorite]


I've never known anyone to be taken aback or shocked out of the mood by a gentle "I'd like to kiss you now" while leaning in and maintaining eye contact.

It's not being "taken aback" or "shocked." It's being disappointed at your lack of confidence, directness, and ability to read her signals.
posted by bingo at 9:21 AM on May 19, 2010 [6 favorites]


Invite her to your place for dinner and a movie and have some wine if you both drink at all. Then it will feel quite natural to move a little closer to her on the couch, offer a massage, etc. Should make it easier to get the physical stuff happening.
posted by orange swan at 9:22 AM on May 19, 2010


A long time ago I pulled the "I'd like to kiss you now" bit and I'm pretty sure by the look on her face that I came across as a complete fool. It seemed like a really good idea at the time though. I wouldn't do it.
posted by greasy_skillet at 9:23 AM on May 19, 2010 [2 favorites]


I don't think there's anything wrong with talking about it - keep it light and simple, don't get all emo about it, but I don't think you can really go wrong with polite honesty. Admit you're rusty and worried about mis-reading signals and doing something unwelcome, and you're accepting thunks on the head with the Clue Stick if necessary. It'll get easier as you feel a little more secure.
posted by Lyn Never at 9:30 AM on May 19, 2010 [2 favorites]


As a fellow shy person, I'm going to give you some advice I'd never follow. She's been on at least 4 dates with you, so minimally she likes you as a friend. So even on the off chance she isn't interested in you "that way" she's not going to be repulsed by a kiss.

So here is the advice. When you knock on her door to pick her up for the next date, give her a quick kiss. (I would preface it with "this is how they say hello in utah", but I don't get out much). That way you don't spend all night getting sweaty palms and heart palpitations, waiting for the moment, looking for excuses not too. Also, nthing don't say "I'd like to kiss you now".
posted by syntheticfaith at 9:31 AM on May 19, 2010


It's being disappointed at your lack of confidence, directness, and ability to read her signals.

Bingo, bingo. I agree.

Keep in mind that she's been continuing to go on fun dates with you for a month. That is part of her sending the signal that it's okay to kiss her. She knows she's sending you that signal. Go for it. In the middle of a nice conversation, or when you walk her to her door, stop talking, wait a beat, wait a beat longer, look into her eyes, and lean in.
posted by juliplease at 9:35 AM on May 19, 2010 [2 favorites]


The first time my current good-time makeout pal and I kissed, I asked for clearance beforehand. Now, she was curled up in my lap at the time and we'd been pretty snuggled up for the entire night, so I was fairly confident of the answer after all the signals we'd been sending each other, but nonetheless I was kind of in your position - just a bit too shy and tenuous to go in without an explicit invitation.

Weeks later, she told me she found this to be sweet and refreshing. Now, the permission requesting is kind of a silly part of our whole thing - sometimes we just go for it, other times we come up with obviously flimsy excuses to request a bit of kissing (viz. good luck, congratulations, brief separations, & c.) So, there's another random datapoint for you from one sort-of couple's experience. Some gals like being asked. Sometimes asking permission is a fine thing. Other times, even shy neurotic messes like ourselves can plainly tell when it's time to draw her to you and plant one.

Could be you're misreading her signs. Could be she's wondering what you're waiting for. There's really only one way to find out for sure. Good luck!
posted by EatTheWeak at 9:36 AM on May 19, 2010 [1 favorite]


Whether stating your intentions will kill the romance or not depends on the woman, as well as your delivery. I would recommend telling her rather than asking her, if you feel you need to say something. Even if you feel scared or shy, you want to project as much confidence as you can.

However, consider this: No matter what approach you take, you might get rejected. Rejection is not the worst thing in the world, though. It means you took a risk, which is something to be proud of. If you go in for a kiss and the woman isn't into it, that's okay. You'll still know that you were gutsy enough to just go for something you wanted (and if you practice going for it even when you feel like you might throw up from fear, it WILL get easier over time).
posted by spinto at 9:39 AM on May 19, 2010


I think you should decide to embrace 'shy straightforwardness' as an endearing attribute.
posted by A Terrible Llama at 9:40 AM on May 19, 2010 [1 favorite]


You could always fall back on what high school boys do: Go see a movie. Sit in the back of the theater. At some point, shift in your seat and casually put your arm around her. Unless she's terminally shy too, she will probably shift a bit and sort of lean into you.

You could also just hold her hand. Being in the dark makes these things easier to do. In either case, though, as long as she doesn't obviously reject these actions, you can assume she'll be okay with a kiss.

As for how to get to the kiss - at the end of the evening, hug her, and hold it for a few seconds. If she doesn't stiffen up and pull back, then kiss her on the cheek. From there, it's pretty easy to shift your head a little so that you're in postion to kiss her on the lips. No, I don't mean slide your lips around her face - just kiss her briefly on the cheek, pull back just a tiny, tiny bit, and then kiss her on the lips.
posted by MexicanYenta at 9:42 AM on May 19, 2010 [1 favorite]


Boy, talk about ask culture versus guess culture. And this makes me wonder... I'm an asker but I'll be darned if I want a guy asking if he can kiss me. Depending on how newly single you are it could take a while for your body to catch up to what's happened. I'm a little over a year divorced and there are times when I still behave like a married person out of habit. Others may have practical advice but I'm thinking maybe you just need time. And lots of
reminders that you're sigle.
posted by madred at 9:43 AM on May 19, 2010


FWIW, I'd be totally grossed out by that.

Well, me too. Now that I read it like that.

Regardless, it works if it seems natural, it doesn't if it seems forced. Same as anything. OP, don't take my advice, or anyone else's, if it doesn't feel like you.
posted by 256 at 9:44 AM on May 19, 2010


I've been in this situation before. It turned out the lack of green-light feelings were due to two factors: she was on the fence for reasons external to our situation, and she thought asking was silly and men were supposed to nut up and take the initiative. I finally blurted out "can I kiss you?" (well, in German) and felt like a total idiot afterward. But in retrospect I don't regret it.

So YMMV, as others have said. My advice: don't think about it too much! Realize that this is something you want, and having pleasant conversations forever in limbo is something you don't want. Get it over with.
posted by ropeladder at 9:47 AM on May 19, 2010


"I'd like to kiss you now."

I have, on two occasions, said, "What do you think would happen if I tried to kiss you right now?" Both times, this was met with giggles, and then great long kisses.
posted by Danf at 9:47 AM on May 19, 2010 [1 favorite]


My rule for when asking is required:
- if you two are on a date (clearly defined as such), then there is no need to ask if you can kiss her, and personally I'd find that a bit off-putting.
- if you're friends hanging out and you'd like to take it to the next level, you may want to ask.

I think this is less about needing to ask, though, because it sounds like you do pick up on some signals - and keep in mind that getting a 2nd/3rd/4th date is pretty much the best signal you can get short of a verbal 'kiss me now'. It sounds like you're more concerned about pushing yourself on someone who doesn't want you.

If you're in a dating situation and not pursuing friends, don't worry so much about 'crossing the line'. Kissing is part of dating, and if she doesn't like it she can simply not go on another date with you. Really, unless you're totally inappropriate physically (continuing after she says no or pulls away), it isn't that big deal even if she's not as interested as you are. (I'm assuming that you're dating women around your own age, ie not teenagers or probable virgins.)

If you are in a pursuing friends situation, then you need to clarify things verbally beforehand. Instead of asking to hang out, ask if you can take her on a date. It doesn't sound like that's what you're doing, though, so I won't go into any more detail about that here.

Good luck!
posted by widdershins at 10:02 AM on May 19, 2010


It does depend on the woman. I am not so aggressive, so the women who are attracted to me don't usually expect me to be, and I do ask sometimes. Have never had a problem with it, but I don't really want to be with someone who can't handle a bit of awkwardness anyway. If everything has to be perfect for it to work for the other person, IMO that's too much to expect of anyone, so just do what comes naturally, asking or otherwise.
posted by krinklyfig at 10:04 AM on May 19, 2010 [1 favorite]


Pleaaaaase don't say, "I'd like to kiss you now." Please. I had a guy do that ONCE, a number of years ago. Much like accidentally ingesting a gnat while bike-riding down a hill, the memory brings an icky taste to my mouth to this DAY.

My vote: try quasi-platonic physical gestures which can easily blossom into EXPLICITLY non-platonic ones. At the end of my first date with my boyfriend, we jokingly stood back-to-back to compare heights (touch! non-weird touch!). Then, I did some goofy yoga stretches and mentioned that my neck was sore (neck rub! yay!). This led very organically to kissing... and, uh, other things. ;-)
posted by julthumbscrew at 10:06 AM on May 19, 2010


From the female perspective: Please do not ask for permission to kiss her. I suggest finding an opportunity to hold her hand, ideally with cause -- i.e., crossing a street, or escorting her through a busy/poorly lit parking lot. Be careful to match her walking speed; you don't want to use a grip of death, or pull her along behind yourself. This scenario will give you the opportunity to convey warmth and thoughtfulness without appearing awkward or aggressive. If she is interested, as I suspect she is, your actions will be reciprocated and things will progress from there.
posted by biggity at 10:49 AM on May 19, 2010 [3 favorites]


I'd say mention your reluctance briefly and keep it light. I agree with everyone who has said she is not repulsed by you as evidenced by her continuing to date you. Of course you already know that. So, start with something less intimate than a kiss, like holding hands or a hug.
posted by soelo at 10:57 AM on May 19, 2010


Maybe it's the ask versus guess culture thing, but if it is, in this case, paradoxically, asking is what a guess person does.

I have never (yet!) initiated a first kiss. Like you, that leads to a lot of going home feeling like a loser, because in this world, most women expect you to make the move. If you don't, they either assume you are not interested, or they lose interest in you because of the lack of confidence. It might not be great to hear, but its the truth. If you are shy, and have a hard time imagining just leaning in for a kiss when the moment feels right, you are going to miss out on getting to know a lot of really great women. I should know.

You're expected to know how to do these things, and there's is not so much hope except to buckle down and work on it. All the lucky bastards who had friends and social groups and figured this shit out in high school won't stop to wonder why you are just sitting there not talking to anyone. Or why you are not leaning in for a kiss. They will just assume you want to be left alone and move on.

Try not to hate them too much. People like julthumbscrew are not malicious, they just don't understand what it is like to have never had anything lead organically to anything.

The only way to do it is to do it.
posted by Nothing at 11:01 AM on May 19, 2010


(And I am sorry, that was not meant as a call-out or anything. It was just the post visible as I was typing mine. I really do think that a lot of people don't know what it's like to have never had an easy interaction with someone.)
posted by Nothing at 11:13 AM on May 19, 2010


Nothing: not to get defensive, but I know EXACTLY what it's like. I'm well-accustomed to feeling horrifically socially awkward, or like "everyone else" figured out how to nudge social/romantic situations in the right direction back in high school.

That being said: I fully agree with you on the "buckle down and work on it". That's why I wasn't in favor of asking permission... you have to bust painfully outside of your comfort zone on these things sometimes. The thing which is hardest for you to do is paradoxically sometimes the one thing which will make you feel more "normal", once it's been done.
posted by julthumbscrew at 11:14 AM on May 19, 2010


Fair enough. It was a bad move on my part. The point I wanted to make is that it's really easy to get resentful, and that only makes it harder. I didn't need to make assumptions about anyone to do that.
posted by Nothing at 11:25 AM on May 19, 2010


Someone upthread might have said this already, in which case just count this as a vote for: don't talk to her, just kiss her. And to help with your confidence, up the stakes a little.

Because there's more to this than body language. I'm also terrible at reading implicit interest in terms of body language and am very often taken aback when someone makes a move or says something outright flirty. But I'm put off only when I'm not feeling the same way or if it's very early in our acquaintance or if it's been so long that such a move totally changes the mutually established tone of the relationship. Clearly, none of those things are happening here!

Also have you considered the possibility that she might be equally bad at expressing herself through body language? So many of us are.

I mean: you've been out together, what, four times? You have a really good time together and are confident that she's at least a little interested. Unless these are group outings or work-related or just convenient get togethers (like, hey we work in the same building and we have the same lunch time or we both like going to the same restaurant on Thurdays or something)... then she has given you enough signals already - by continuing to go out with you. Where else does dating go?

This is the safest spot, in terms of timing - you can be confident that she wants you to make a move and it's (most likely) not too late that she has begun thinking of you as a platonic friend. Ask her out again, make it a little more date-y than in the past -- dress up nicer, take her to a quieter place, get more personal in your conversation. This way you'll build up to the kiss and have plenty of time to gain confidence from her participation in the date. If, when you get date-y she gets date-y too, and the night goes well, then you can (you should) really kiss her without worrying about crossing any lines.

These social conventions are made to guide and protect socially inept people like you and me. :) Go for it.
posted by mondaygreens at 11:53 AM on May 19, 2010


offer a massage, etc.

Since we're fessing up here, I find this one nasty. If a guy wants to touch me, don't go around the long way by pretending to want to give me a rubdown. Unless you're actually a massage therapist, it's a bogus way to get to touch a woman. If I want a massage I book a massage. If I want to kiss a guy, that's something completely different.
posted by zadcat at 12:24 PM on May 19, 2010 [4 favorites]


Maybe the problem is the expectation that you go home as a loser. What is wrong with having a nice time with this woman and developing a friendship with her, allwoing intimacy to take a natural course?

I think that you both will know the right moment. You can't make it happen. If you attend to her comfort and enjoyment when she is with you and truly enjoy her company, then it should not be a problem to wait until you neither need to ask or guess -- You'll know.
posted by cross_impact at 12:56 PM on May 19, 2010


Do not do that thing Patrick Swayze does to the doctor woman in Road House where he suddenly lunges in like a xenomorph and throws his tongue into her uvula. Other than that, I think you're OK just kind of putting a little extra pressure into the next hug or whatever and moving your face into rough alignment.
posted by fairytale of los angeles at 1:16 PM on May 19, 2010 [1 favorite]


You gotta make the move (always). Take a shot of tequilla before you go out, loosen up, free yourself from your mental inhibitions. You can do it!!!
posted by Hurst at 1:35 PM on May 19, 2010


Four dates? She's waiting for you to kiss her. And please don't ask for permission, it really is offputting. When you say goodnight/goodbye (always a good/expected smooch moment) reach out and stroke her hair, gently. Or as someone else suggested, kiss her hand. Unless she flinches violently, you may then go ahead and kiss her.
posted by uans at 3:50 PM on May 19, 2010


38 y/o kinda-shy male here.

I wouldn't go the "I want to kiss you now" route. I can see how women could see that as a bit cowardly (but then, some will find it refreshingly cute too).

I've done the completely out of the blue (usually drunken) lunge-kiss. That will either go REALLY bad, or REALLY good.

But you can "ask for permission" without saying anything. If you've dated 4 or 5 times, you should be able to just generally get closer, physically. If you're sitting next to each other on barstools, or on a sofa, sit closer to her - let your legs make contact. Just a bit, but she will notice. Lean in, put your hand around her shoulder and whisper a silly secret into her ear. ("That guy over there has NO fashion sense", or whatever).

Ask to look at her ring, and hold her hand as you study and ask about the ring. Brush stray hairs (dust, lint, cigarette ash, whatever) off her clothing. When you're walking along the street together, make sure you at least brush arms or hips a bit. Even better would be to hold hands.

How she reacts to these little encounters of contact should give you an idea of how she would react to a kiss, and it will break that first physical contact hurdle, and get both of you "in the mood" for what's coming.

When the time is right, which you will know, just look into her eyes, say nothing, pull her closer, and plant it.

Take my advice with a grain of salt. I am by no means an expert. Good luck!
posted by Diag at 3:52 PM on May 19, 2010


Before our first kiss, the love of my life said "I'd like to kiss you now, but I'm too nervous".

My response? "Bring it on!" Still kissin' 18 months later. YMMV, but I hope not!
posted by malibustacey9999 at 4:55 PM on May 19, 2010


I am totally in favor of the shy awkward bluntness of simply saying something like "I'd really like to kiss you." It's pretty much what I (female) did when initiating things with my husband, 7ish years ago. Worked out great for me.

Sure, it'll be a mood killer for some people. So what? It'll work for others. And if it calms you down, great, go for it.
posted by Eshkol at 7:31 PM on May 19, 2010


It depends how you ask. And seriously, if you're nervous about it she probably knows that. Don't go for the mood in an avert way, and certainly don't offer a massage. There is nothing wrong with asking her if you can kiss her. If she likes you she will smile and you will kiss and fireworks will go off - if the isn't into it, then she never was, and you can maintain your dignity.
posted by the noob at 8:49 PM on May 19, 2010


There's all kinds of stuff you can say and do. Really, if she likes you and wants to be physical with you, you can pretty much do or say anything but "I hate your face", and don't kick her in the shins. Other than that you're pretty much good.

The last guy I started dating did it kinda through a joke. The actual joke was kinda horrible if you put it in print so I won't repeat, but it was basically a half-serious, half-joke "I know you want to kiss me" type thing so I didn't have to actually say yes or no, but the opening was there and it was on the table for me to respond to.

Holding hands is actually the first step for me and most guys. Kissing is really spitty and mouthy and it's easier to just put your hand over really close to hers and see how her hand reacts...she can move away or she can be like "oh hi hand, here is my hand!" and you can keep going that way until you're holding hands. It always gives me a little tingle up my spine.

Oh, one time a guy was looking at me pensively and not talking until I was like "what? what is it?" and he said "I was thinking about whether I should kiss you right now" which was the perfect blend of "I kinda like you, and I'm non-committal, but I could be convinced to kiss you".

Good luck I hope these examples helped.
posted by internet fraud detective squad, station number 9 at 12:16 AM on May 20, 2010


There's also a big difference (to me) between "I'd like to kiss you"/"may I kiss you" and "I have to kiss you now"/"I'm going to kiss you." The first is quaint and, given the people and the situation, could be sweet-cute or offputting. The second is vaguely threatening, with overtones of "whether you like it or not."

I am a survivor of acquaintance rape, FWIW, and I recognize that this is my own baggage. However, it is unlikely that a rape survivor is going to tell you that before a first kiss. Certainly, kiss me if you want to - just don't announce it. That microsecond between statement and kiss is long enough for me to panic.
posted by catlet at 9:55 AM on May 20, 2010


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