Asking out a socially awkward friend
December 11, 2011 4:46 PM   Subscribe

You're a smart, awesome guy with serious social anxiety. What's the least awful way a friend could let you know they have feelings for you?

I'm female, 30, he's in his mid-twenties, and we've been friends for a couple of years. We have a lot of common interests and our friendship's been largely based on meeting one-to-one and talking for hours, with some email and stuff in between. At the time I first met him, I was at the end of a relationship with someone else, and so I couldn't quite tell how I felt about the new friend - I wasn't clear enough in my feelings to make a move that might just be a rebound, partly because I was so excited about the friendship and partly because his self-esteem isn't high enough for me to feel ok about being selfish/reckless.

I'm clear now, though: I turned down a possibility with someone recently because all I could think about was how much more interesting, cute, awesome and smart my friend is. I'd rather be kissing him, hanging out with him, than anyone else - it needn't be any more of a big deal than that.

The complications:
- He's got extreme social anxiety, generally manifested in avoidance. If I make a move and he's not interested, I will probably never hear from him again.
- We live in nearby cities, so I see him with erratic frequency (though this wouldn't be a big issue if we were together, as the distance is short and we both have reasons to be in each city).
- I have an awful lot more experience in relationships that he does, whih I mention only because I know he hasn't done any of these things much - I'm still a total doofus, but I think he's extremely unlikely to make the first move even if he wants to.
- I'd rather stay friends with him than push him away, and I don't think he'll handle it smoothly if he's not interested.
- I'm somewhat socially anxious myself and get really stressed about possibly upsetting people.

We have mutual friends, and I'm considering testing the waters by asking one of them - I'm sure he's been teased about me, but I'm not sure if the response is "shut up" or "hell no, and I wish she'd back off". The only thing is, I'm 30 and that feels totally childish, but also like the only way to get a sense of whether the risk is worthwhile.

Socially anxious MeFites who can identify with my friend: what should I do? Have you had good or bad overtures like this before, and how did they go?
posted by anonymous to Human Relations (35 answers total) 19 users marked this as a favorite
Honestly, other commenters please smack me down hard if this is inappropriate, but as someone who's extremely shy and socially anxious, I'd prefer an email? I know it's a little impersonal to a lot of people but for me it would give me time to turn things over in my mind and figure out how to react, without the old-timey sentimentality of a written note.

The in-person thing most people prefer for big interpersonal interactions would just feel to me like I was being put on the spot. I tend to feel cornered and panicky in such situations. I'd say write an email and explain why you felt an email was a better way to do this.

I don't know, I hope other people weigh in. The only time I ever did this, I did it in an email, and it went fine, but my grasp on these social norms can be pretty tenuous.
posted by troublesome at 5:06 PM on December 11, 2011 [16 favorites]

Maybe you can take baby-steps with him by doing the "invade personal space" test- "invade" his personal space slightly by leaning on his arm, standing very close to him, etc (but for pretty short periods, not several minutes). If he doesn't move away and then starts to invade your personal space too, chances are good that he is interested, too.

also, how does he look at you? with starry eyes (dilated pupils)? Does he look at other parts of your body besides your face sometimes? THese can all be indicators that would would get a positive response.
posted by bearette at 5:08 PM on December 11, 2011

I think bearette's idea could backfire. If he's got social anxiety, and you start invading his personal space in an ambiguous way, you will confuse him, which will increase his anxiety.

I agree with troublesome that email could be a good way to keep this low-stress.

Apart from that, this is really a common question here. My feeling is that you need to tell him you're interested. Risking the loss of your friendship (which it may not come to) is worth it because the current friendship (or "friendship") when you want more is not doing it for you and is not going to until you get some resolution here.
posted by J. Wilson at 5:12 PM on December 11, 2011 [5 favorites]

OK, I know this doesn't sound like the adult way to do it, but I think you should totally test the waters through a mutual friend. Get someone he trusts to get a few drinks in him then tell him a "secret": "I was talking to Anonymous the other day and I'm pretty sure she likes you. Would you go for it if she was into you?"

I know it's so very 8th grade, but we're all kids at heart anyways so you might as well embrace it. If he's like "thanks but no" then you both have plausible deniability and can continue your friendship as you see fit, and if he's into it then you can make the first move without ruining things.
posted by auto-correct at 5:27 PM on December 11, 2011 [9 favorites]

Don't ask mutual friends.

troublesome, the email idea, it's not bad. I'm sure if I had more social issues, the idea of getting an email, being able to react on my own terms in my own time, it's kind of nice. (In fact, it's why I love email.) But if you're friendly with him and already spend hours together I'd opt for in person.

bearette, all those flirting things are great for when people just want to test the waters and be all ambiguous and vague. If you want a definitive, certain answer, the best thing to do is ask outright. Why muddy the waters?

Next time you're hanging out, towards the end of the hanging out (you don't want to spring this right before you're about to head to a movie theater/place to eat), in a private, quiet place (ideally your home or his, though certainly his home since [a] he'll feel more at ease, [b] you can get up and leave (and you should plan to be leaving anyhow!) as opposed to him feeling like he needs to run out of strange place because he's freaking out) tell him the following, gauging his reaction to each (but still remembering that you might not be reading him right and some sort of direct response from him is really ideal):
  1. Hey Frank, mind if we talk quick before I leave?
  2. First, I know me saying this might make you bug out as you jump to conclusions, but trust me it's a good thing. No matter what, you're my best friend and you mean the world to me and I would never want to do anything that would ruin that.
  3. I like you in a way that's beyond being friends. I like you tons and think you're an amazing person.
  4. I don't know how you feel about me, and it's OK if you don't feel the same.
  5. But I really do like you and if you think there's a chance you might feel the same way, I'd like to start seeing you on a more than friends basis.
At this point, he's probably said something. Maybe after number four with a "no, I really like you too" or maybe after three he leaned in and kissed you. Or, sadly, maybe after five he said "I'm sorry, you're an amazing friend, but I just don't feel the same way". (This is when you take advantage of hanging out time being over and tell him you hope things will still be the same between you, friendship-wise.)

But maybe he's said nothing. Now's when you say "hey, look, think about this if you need, sort things out in your head, give me a call/text/email, you know where to find me" and again do that leaving thing.
posted by Brian Puccio at 5:28 PM on December 11, 2011 [11 favorites]

If he's really that anxious that even you hinting verbally that you might like him that way would cause him to avoid you forever, then I don't see the drawback to having a friend ask him how he feels about you. They don't have to say that you put them up to it, they can just be like "oh, you and anonymous are so close, sometimes I think you would be a great couple" and see what he says.
posted by treehorn+bunny at 5:28 PM on December 11, 2011 [2 favorites]

Otoh the way I got rid of my own severe social anxiety was by getting my first serious bf. Give the guy a chance!
posted by St. Alia of the Bunnies at 5:34 PM on December 11, 2011 [2 favorites]

I am a socially anxious person, and I really appreciate directness and clarity. My friends and I were talking about this recently, and we agreed that the advantage of directness is that if someone has been really direct in asking you out or telling you they're attracted to you, it's easier to be direct back--the person has basically established a situation where openness/bluntness is OK.

Also, he's anxious and avoidant and inexperienced, so I wouldn't count on cues like how he handles you invading his personal space or whether he invades yours being accurate indicators of anything. I would also not count 100% on what your mutual friends might say or think.

For me, an email or text would be fine. And preferable, really, especially if it turned out I'm not interested.

Give him the benefit of the doubt with regards to being able to handle things if he's not attracted to you. If you don't hear from him again, you can reach out (not over and over, but once or twice), and be clear, again--this time, being clear that you're not trying to chase him, that that idea is done and buried, but that you would like to remain (just) friends.
posted by needs more cowbell at 5:42 PM on December 11, 2011 [4 favorites]

As a guy who somewhat identifies with the object of your affections, I know that I have a hell of a hard time picking up on body language & social cues (specifically, I have a very difficult time differentiating between woman who is merely friendly and woman who is romantically interested).

I know that I would very much appreciate something that was direct, up front, & honest. This could be in the form of a well thought out email, in person conversation, or something else appropriate. Email might be slightly better, because in response it would give me time to think & compose my thoughts well.

As far as what to say, something like what Brian Puccio wrote would very much do the job.
posted by AMSBoethius at 5:44 PM on December 11, 2011

Go out to dinner, get some wine in him. Be forward. People that are socially anxious tend to have a really hard time reading social cues from people. Don't expect him to guess, just tell him.
posted by empath at 5:50 PM on December 11, 2011 [3 favorites]

Otoh the way I got rid of my own severe social anxiety was by getting my first serious bf. Give the guy a chance!

Succinctly what I was about to say. And hey! I'm going to say it anyway!

I've been in your situation a number of times. I've had friends in your situation and friends in his situation. He most likely needs a shepherd.

Ask some friends their opinions just to make sure you're not totally off-base, and then take charge like crazy if you get the go-ahead. Some of my good friends are living out the fruits of this exact situation right now. She's a little older (near thirty) and has a lot of history, he's a little younger (mid-twenties) and is cute and great and smart and had almost no social confidence or experience before she took the initiative.

And oh my lord was the story of her taking the initiative a train wreck. Just classically awful. She was drunk and had already been making out with my roommate for the first time at a party at our apartment after publicly pining over my roommate for some time. Then she went to get another drink, met Dude in the kitchen, and then pulled him into my laundry room and shut the door. Leading to concerned parties intentionally/accidentally walking in on them in order to gauge/stop the situation. Nothing could have been more awkward for the Dude involved. And she stayed with my roommate that night, to boot

But he got over it very quickly, and the two moved in together not long afterwards and are great. The roommate is close with both of them, as am I. His confidence is markedly up, ad everyone is glad for the potential she saw in him.

So check the waters, and if they are clear, jump in head first.
posted by Navelgazer at 5:51 PM on December 11, 2011

I have AvPD. You need to communicate three things:

1. I like you
2. I hope you like me
3. It is totally safe to tell me you either do or do not like me back, and there is no way you can screw this up.

And you need to do it in a way that is totally unambiguous (because the more severe social anxiety you have, the more you're looking for signs of rejection or risk) and low-pressure.

So, an email (not a text, not a phone call, not an in-person meeting, not a message between buddies) that hits these major points:

A) I like being your friend a lot, and
B) I specifically think you are interesting, funny, and smart.
C) That time you did X was awesome, or I too am interested in Y, or some other "we have things in common and have things we can talk to each other about" reference (be concrete)
D) I don't want to put any kind of pressure on you - things like this make me nervous too!
E) I sort of have a feeling some of our mutual friends have brought this up, and I'm sorry if that's freaked you out.
F) I'd be a lot more comfortable if we could both gain some clarity about this, because I'm becoming uncomfortable,
G) And it's OK if you're not really into me, I promise,
H) I still want to hang out with you and be your friend either way, and swear I won't be weird.
I) Send me an email or something if you'd be interested in doing Z (specific thing on specific day) or another date kind of thing.

If he's avoidant, the key thing is to reduce the number of things he can get wrong. He needs to perceive the entire thing as a low-demanding situation, and you as a non-threat. Ambiguity and games and guessing and leaving stuff between the lines are your enemy here.
posted by Fee Phi Faux Phumb I Smell t'Socks o' a Puppetman! at 5:55 PM on December 11, 2011 [48 favorites]

The blunt approach might work, or it might not. Even if he is interested, if he is of the anxious persuasion, and he knows that you have more experience in these affairs, being overly direct might backfire and cause him to withdraw.

Some people may not like this, but FWIW... alcohol can be great in these situations.

I'm not saying you should get him blotto. And I'm not saying you should try to seduce him while he's drunk. But a few drinks in a private environment where you are both comfortable over the course of a few hours can be great way to relax inhibitions. Have a nice evening, git a little tipsy, and see where things lead. ;)
posted by rabbitfufu at 6:01 PM on December 11, 2011 [1 favorite]

Smile, eye contact, compliment. Since the dawn of time this is how it has been done.
posted by Ironmouth at 6:16 PM on December 11, 2011 [2 favorites]

Well, my ideas were a way for you to test the waters to see if he is interested, not a way for you to let him know you are interested. My point was that if he is not bothered or does not move away when you touch him more, you'd be less likely to be rejected when telling him you have feelings- the touching was not the way I was suggesting to tell him, since it is ambiguous.

If his anxiety around you is so severe that he likes you but can't stand to be touched by you, I'd question whether he is ready for a relationship with you in the first place. I could be wrong, but that's my though.
posted by bearette at 6:45 PM on December 11, 2011

Ha! I love this question!

When I first met my husband, in a work situation, I thought he was just awesome but a little younger than me, and so so attractive, I thought he'd never like me. But we had a "click."

We got married 2 months later, long story there. But I found out he was teased at the office that I was his "girlfriend," and he quipped back, " No, she's my wife!" So apparently we were on the same page there.

One of my best male friends, who I just saw today.... I liked him at one point. Turns out it was misguided because as much as I still LOVE friend, wow, he would have been a bad match for me. He's finally with someone I think he will marry. I hope so.

After a Christmas party 6 years ago I finally told friend I liked liked him. He was pretty cool about letting me down - so nice about it. We've remained really close. I'm so glad he never dated me. My husband is actually a little younger than friend, but so much more emotionally together.


My point is that if your friend can't turn you down and remain your friend, uh, he's not going to be your friend five years from now, anyway. My friend is still a friend for life. See the difference?


You have nothing to lose! Go for it!
posted by jbenben at 7:04 PM on December 11, 2011

Keep things simple. Do not ask friends. They won't know the answer anyway (socially anxious people don't confide in anyone about crushes) and they will amp of the stress for both of you.

Start by hugging him whenever you say hello or goodbye, short hugs at first, then longer. Touch him whenever you have the chance. This will get you into his space in way that will get him to think about what he wants. He may not think he has a chance with you and has, as this time, no inclination for taking things to a romantic level. By touching him more, you are getting him to think more about you and the possibility of other things.

Seduce him. Slowly. Do not send mixed signals. If you get nervous and pull back it will confuse him more. Do everything you can to let the first move seem like his idea. Don't get discouraged if he doesn't make that move on your timeline.
posted by myselfasme at 7:19 PM on December 11, 2011

I'd worry less about the asking, and more about what comes afterwards. Us socially anxious types, we can be a bit of a handful sometimes. You have to be sure that you can handle someone who might disappear for days, or who'd find it incredibly difficult to articulate when he needs something to change. If you have fear of abandonment, or a strong temper, you may want to reconsider this potential relationship.

Ok, say you've decided you're still interested. Still, I wouldn't concentrate particularly on asking him out. If he's likely to react badly to that situation, then even if you arrange a magical way to make that one event less anxious, other situations will arise that you're less prepared for. I would counsel you instead to make yourself a close enough and comfortable enough friend that it at least partly overrides his anxiety. Then, when you tell him "I like you, but I'm still here if you're not interested", he'll actually believe you!

Getting to that point is unfortunately pretty hard. Using non-immediate communication like email, as others have recommended, is one good technique. Reinforcing that your friendship is more important than any small problem helps too: once there have been many incidences when you've offered small criticisms while emphasizing that you're still there for him, scarier situations will be easier. Perhaps the most important thing is being able to talk explicitly about his anxiety, but please don't force that, it has to come with time. I wish I could be more helpful!
posted by vasi at 7:21 PM on December 11, 2011 [1 favorite]

As soon as I read this I thought "email" because I love email too and avoid uncomfortable conversations most of the time. If he doesn't like you back he can pretty much pretend he didn't read the email and life goes on as normal (with a bit of mental awkwardness on most part but it will go away pretty quickly I would assume). He can respond however he wants on his own time. Face to face is too much pressure. In my romantically-useless/ineffective opinion!! I doubt this method would ruin your friendship as well, as long as you emphasized your complete and total acceptance of his answer either way.

Also this may be sexist but I just watched When Harry Met Sally again yesterday and I would hesistate to say that if you are good friends, and he is very shy then there is a strong possibility that he feels the same way and will respond positively. And if you do it by email (broach the subject in a conflict-avoidant way) then there is also a chance you will also have a 'you've got mail' situation going on- even though that was a terrible movie. Both ended happily however, which I guess is the take home message. I had it worded better originally but my small type got deleted accidentally the first time.
posted by bquarters at 7:36 PM on December 11, 2011

I am not sure why asking a friend to run interference is such a bad idea, although it would have to be the right person. I say that because I know of two introverted couples where the way they got together was due to friends engineering things. Of course, in both cases it was a friend (different friends in each case) taking things into their own hands and saying to the guy "no, seriously, she likes you, will you just ask her out already??" And, in both cases, the guy had no idea that she liked him until it was pointed out to him so directly. These are all people in their 30s, by the way, not high school kids or anything.

I'm not necessarily saying that it's the right approach here, I just wanted to say that it's not always a bad idea...
posted by cabingirl at 7:48 PM on December 11, 2011

I must be missing the point here: I don't understand why you don't ask him out for a date. "I would really like to go out for a fun, romantic dinner with you. I really like you a lot and would like to spend time with you doing that. Or maybe you would let me cook you dinner." et cetera. Sure, you can do it by email. I do not think it is necessary to elaborate on your feelings more than that. I think there is little or no ambiguity to this message.
posted by Mr. Justice at 8:15 PM on December 11, 2011 [1 favorite]

Another socially anxious guy voting for email, here.
posted by Tell Me No Lies at 11:22 PM on December 11, 2011

I have a social anxious male friend who sounds EXACTLY like your description. The chances of him asking someone out are about 1% and he has low self-esteem and finds it hard to believe that others are attracted to him, despite the fact that he's smoking hot and a great guy.

I'm going to go with the direct approach too and I think e-mail is fine.
posted by Ms. Moonlight at 11:59 PM on December 11, 2011

I'm a socially awkward guy and I like the idea of an email but would find a letter even better. It doesn't have to be pages and pages of sonnets written on parchment. Just an affectionate and clear message telling how you feel. If you have nice handwriting then write it by hand, if not then just type it out, print it and sign it yourself.

I prefer the idea of a letter to email because it separates it from your normal method of communication which will give him a small clue that it is something special before he reads it and it will make the whole thing a bit more concrete and 'real' for him if there is something he can hold in his hand. Whatever his reaction he will most likely be completely flattered and a letter is something he can keep and treasure.
posted by neilb449 at 12:04 AM on December 12, 2011 [1 favorite]

Yes us socially awkward people do like our email. Plus direct, succinct, and sincere.
posted by mleigh at 2:23 AM on December 12, 2011 [1 favorite]

I don't want to offend anyone here, so I hope that this is taken as a sincere, non-judgmental question:

If this guy is so socially awkward that you can't talk about your feelings with him in person, why do you imagine that the kissing will be any good?

It is wonderful that you feel strongly enough about him to accomodate his social anxiety. But, if you start off like this, then, do you imagine that he'll grow out of his social anxiety? —Or are you prepared to forever accomodate it?

When you get into fights, how will you feel if he disengages, slinking away to his computer? When you need to have a difficult talk about why the relationship is not working, how are you going to react if he is too afraid to even listen? And when you mention kissing in your question, are you imagining emotionally-present passion, or the physical equivalent of emoticons?
posted by esprit de l'escalier at 3:05 AM on December 12, 2011 [4 favorites]

If you are concerned he may simply vanish if he is not interested, it may help to spell out how he can handle it:

[snipping imaginary first part of your email] So, Bob, that's how I feel. If you aren't interested, I would like to remain friends. I know it can be awkward, but if you tell me you just want to be friends, I'll respect your feelings and won't bring this up again unless you bring it up yourself.

I'm really anxious about these situations myself and in some cases having an agreed-upon "when X happens, it is acceptable to Y" can make the difference between me quietly freaking out in my head to me carrying out Y with relative calmness.

If you two do get involved romantically, I think it's a good idea to have some "how we want to be together" talks. It could be as simple as watching movies together. "Wow, look at the way he's yelling at her just because Z. I'd never yell at you if Z. What do you think is acceptable?" Extrapolating from my own experience, the disappearances might have to do with not knowing how to express himself when he is upset about something or needs something.
posted by bunderful at 5:58 AM on December 12, 2011

Ooops. That second paragraph should have had quotes around it.
posted by bunderful at 5:59 AM on December 12, 2011

If this guy is so socially awkward that you can't talk about your feelings with him in person, why do you imagine that the kissing will be any good?

My experience with being socially anxious and also dating people that are socially anxious is that once you get 'over the hump' with someone, they have no problem being affectionate, loving, etc.. The hard part is negotiating closeness but once you're there, it gets a lot easier.
posted by empath at 6:01 AM on December 12, 2011 [4 favorites]

I understand why an email might sound like a good idea, to give him time to process the information, but I have to disagree about using email. Lets say he reads it, and even if he is interested, do you really expect a socially awkward friend to either write back to you and say "oh yes, I am interested too, lets go out" or to see you in person and have the guts to say anything about the email?? I think an email would get you silence, and would give him wayyyy too much time to overthink things before he sees you, even if he likes you. The first meeting after the email will be so awkward that he might just keep avoiding you to avoid the awkwardness.

Having a friend ask will also give him way too much time to get nervous and anxious about it after he talks to the mutual friend.

In general, using friends or a big confession of feelings usually ends up bad, whether the person is socially awkward or not.

Do you guys chat online (facebook, gmail, AIM)?. I would try flirting with him there, if you think regular flirting in person will make him run away. Do you guys do things that involve drinks? Alcohol helps in any situation. Can you make plans to watch a movie or cook dinner at each other's house (with some wine or beer)? Do things other than getting together for dinner, and test the water with some light arm touching and flirting. If he doesn't respond, then back off.

Also, I know that once someone gets over the hump, as empath says, they can be totally normal and affectionate and not socially awkward in a relationship, but it's still something to think about... do you want someone who might never take charge? Who will avoid difficult conversations in a relationship because they are anxious about them? As much as you might like him, think about whether this will be something that you want, or whether you'll have to drag him along in the relationship constantly.
posted by at 6:48 AM on December 12, 2011 [1 favorite]

I just want to clarify what I wrote.

You obviously have feelings for him if you're rejecting other lovers on his account. I wasn't suggesting that you doubt your heart's choice.

I was trying to say that if you are not prepared to forever bend over backwards for his social anxiety, then maybe you should meet him half way right at the start. I was suggesting that you be patient and open-minded in person.
posted by esprit de l'escalier at 7:20 AM on December 12, 2011 [1 favorite]

I wish I could favorite Fee Phi Faux Phumb I Smell t'Socks o' a Puppetman!'s comment even more.

There's a chance that even if you get "over the hump" with this guy, he will still be the same social anxious/awkward person you adore. People who are social anxious and/or awkward can still be loving and affectionate, they are just loving and affectionate in different ways.
posted by Wuggie Norple at 6:52 PM on December 12, 2011

I prefer people to ask me out on a date, rather than say "I have feelings for you." Saying "Hey, are you interested in going out on a date?" makes it possible to turn them down without feeling like you're crushing them, and for less awkwardness afterwards if the answer is no. Less awkwardness = more chance of remaining friends.

Ditto all the other advice about being direct, though.
posted by thelastcamel at 5:47 PM on December 14, 2011 [1 favorite]

Mod note: From the OP:
He said yes, he said yes, he said yes! I finally asked, and in a couple of weeks (damn logistics!), we're going out.

I asked by email, kept it short and made it clear, "I like you! Do you want to go on a date?" rather than a massive confession, and he replied quickly - I think I underestimated him. Fee Phi's suggestion seemed clear and fair, and like something I'd appreciate myself, so I did a low-key version of all those points.

Thanks so much for helping me think this out properly! A great start to the year so far.
posted by restless_nomad (staff) at 11:48 AM on January 2, 2012 [8 favorites]

posted by Tell Me No Lies at 1:23 PM on January 2, 2012 [1 favorite]

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