How do a Shy Girl and a Shy Guy Get Together?
December 30, 2011 11:35 PM   Subscribe

How do I approach a shy guy, or how do shy guys like to be approached?

I have a mad crush on a guy at work. I haven't had one of these since i-don't-know-when. I've taken to barely looking at him cuz I'm embarassed that he might know that I'm totally crushing on him. Maybe it's one-sided, but I feel an energy when I'm near him.

We work in different departments and are both seasonal staff so potential romance won't necessarily jeopardize our jobs.

The thing is, we're BOTH super-shy types who are bad at small talk. Him a tad more than me. If we walk past each other, half the time he's too shy to look at me and if I say Hi, he often doesn't even make a peep. The other day I was in his department looking for something. I asked him if he knows where I could find it and he kinda froze up. I saw what I was looking for a few seconds later, and said "It's OK, I see it now." Again, not a peep. I'm frankly baffled to meet someone more socially awkward than me.

He is well-liked by people, and I do see him talking with his department mates sometimes, so he's not necessarily unfriendly... though he definitely has a charming awkwardness to him.

Part of me is resigned to nothing happening because I have no clue what to do. If you were me, and you wanted to see if there was a chance with this guy for you, what would you do?

Or, if you are a shy guy, how would you like a woman who's possibly interested in you to interact with you? Would you want her to bluntly ask you out? Try to engage you in conversation for a while first?
posted by oceanview to Human Relations (21 answers total) 13 users marked this as a favorite
Get right to the heart of the matter. Ask him out. You both seem to be awkward in conversation. Make it a specific yes/no question. "Hey, do you want to go to the poetry reading on Friday at 8:00?"
posted by JohnnyGunn at 11:51 PM on December 30, 2011 [1 favorite]

You're gonna hafta drag this horse to the watering trough and force him to drink, but go he will.
posted by Ardiril at 11:54 PM on December 30, 2011 [3 favorites]

As a person of imperfect social graces myself, I theorize that I'd prefer such shocking announcements via asynchronous communication - letter, text message, email - to allow it to be properly digested without fear of messing up the response while overwhelmed with feelings.

My current girlfriend cornered me at the coffee machine a couple of days after telling a mutual friend about her intentions, so I had advance warning. I think this was a lucky accident and not the result of clever planning, though.
posted by themel at 11:55 PM on December 30, 2011 [2 favorites]

Yeah, I think Facebook was made for this situation. Friend him, and if he accepts, send him a note there inviting him to do something specific.
posted by Monsieur Caution at 12:01 AM on December 31, 2011 [5 favorites]

Being socially awkward myself (male here), I may not be much help. From what I experience, being socially awkward means that I'm always fantasizing about a potential relationship and million other ideas that could go wrong, which leads to the paranoia and social awkwardness. I talk to guys a lot better than when I do with women I like (I can talk to women I don't like passionately, though), so maybe your crush and I are in the same boat.

Here's how I would like to have a woman interact with me:
* Smile and say hi to me everyday, occasionally bringing up a conversation. It might be hard, but anything is better than nothing (but keep it relevant and SFW until you get to know him)
* Ask me out to places. Being socially awkward, I don't get invited to many places or I feel awkward being the one to invite people. Don't make it places where there are too many people.
* Be patient. Continue to ask him out to places. The first couple of dates he's probably going to go through a series of doubts and self-questionings (or at least that's what I do).

I'm currently going through sleep deprivation, so my advice may not be up-to-par.

Oh, and a warning, if he's anything like me, if in the event that he isn't what you thought he is, do not, I repeat, do not play him on. Let him down gently, but with a firm declaration that you don't plan on furthering the relationship. It drove me crazy to the brink of isolation when one of my ex-girlfriends decided to just ignore me and not tell me that she didn't want to have anything to do with me.
posted by Angel of Khaos at 12:04 AM on December 31, 2011 [2 favorites]

I'm him. You should just ask him what he's doing on the weekend or something. If it's something you can do with him, ask if you can go too. If not or he doesn't have plans, ask him if he wants to go do something with you.

NOT dinner. The thought of being one-on-one and having to come up with a conversation for an hour is terrifying. He will probably turn that down just out of fear. Maybe a walk at a nearby hiking trail or something.

Then be prepared to do a lot of decision-making that day, because you'll probably wind up with a lot of "I don't know what do you want/I don't know what do you want" awkwardness otherwise.

The good news is, at least for me, that only lasts for the first outing or so. Then I get more comfortable.
posted by ctmf at 12:29 AM on December 31, 2011

Email is generally best. It alleviates a lot of on-the-spot pressure. Bluntly asking out via email does tend to sort these things out fairly quickly without too much of the angst.

To converse with him - ask him direct questions. Show your interest in his answers. Do not randomly walk into a room, say things randomly, and expect a response from him. As you've seen, it doesn't work. Unless you go in directly, there's going to be a lot of umm, err...what do you want from me? And that kind of crap can go on for years if you let it.
posted by mleigh at 12:41 AM on December 31, 2011

Listen, I'm a guy.. an introvert... and I'll tell you what I tell all my female friends about how to approach a guy.

Go up to him and, ensuring that there's no ambiguity and no room for him to wonder if you're joking (we men are bad at reading between the lines), straight up tell him you're into him and ask them out.. Unless they're gay or taken, it's practically a given that they'll say yes. It's that easy.

Why? Because being approached or asked out by a woman is so rare that it's cool and incredibly flattering that we'll say yes based on this alone. If you're cute and/or a cool person it's an added bonus.

So seriously, just tell him you like him and you want to go out. Unless he's gay or taken, I calculate a 99% chance that he'll say yes.
posted by Effigy2000 at 1:20 AM on December 31, 2011 [10 favorites]

I'd vote for asking him out directly but via email/text/letter.

If it were me I'd say 'yes' if asked directly but I would say it coherently if you gave me a little bit of time to process before I had to reply.

And if you do want to just engage him in some conversations then you will need to initiate them by asking him specific (not standard small talk) questions and volunteering information about yourself. I guarantee he'll be delighted and able to hold a nice conversation with you if you give him a nudge in the right direction.

Have fun, and thanks for noticing the shy guy!
posted by neilb449 at 1:47 AM on December 31, 2011

"Hey, do you, y'know, wanna-grab-a-coffee-sometime?"
posted by DisreputableDog at 2:48 AM on December 31, 2011

Agree with everything - encourage starting with emails. Moving to text ("hey, can I have your number so I can text you sometime?") is a fun step.
posted by jragon at 6:42 AM on December 31, 2011

As someone who was once married to a "shy guy" I disagree with all of these responses, and reconsider asking the question altogether. What you are doing is hoping to start a relationship that is based on your trying to read his mind, and him not having to take any action to communicate with you at all. The way you start your relationship sets the tone for how it will be. You are trying to figure him out without talking to him, and guessing at what his silences may mean. Unless you are a mind-reader, it's an ineffective means of communication.

You are questioning, guessing, hoping, and creating positive vibes out of whole cloth (I feel an energy when I'm near him, he's not necessarily unfriendly, has a charming awkwardness) with regard to a person who will not speak to you! (if I say Hi, he often doesn't even make a peep...I asked him if he knows where I could find it and ... Again, not a peep....I do see him talking with his department mates sometimes)

If not for the crush, would you consider his behavior charming?
posted by headnsouth at 7:21 AM on December 31, 2011 [9 favorites]

Ask him out in a way that doesn't allow his self-effacing nature to brush it off as you meaning something else. Be direct. In short, exactly what Effigy2000 said.

headnsouth makes a worthwhile point about you imagining too much, but I don't think it should stop you from making a move; instead, take it as a caution against assuming. It's not wrong to feel attracted to him, but it WOULD be wrong to construct a false understanding of him as a way of bolstering your courage. It's easy to do and it will be a barrier to any worthwhile kind of relationship. So quite simply, just go and ask him before your mind gets too carried away by the crush-y feelings.
posted by fearnothing at 7:55 AM on December 31, 2011

but go he will.

Don't be so sure. Do you have any indication that he likes you? If he's physically attracted, you should have received some signal by now. If not, you may be setting yourself up for a brutal rejection (the aftershocks of which might screw up your relations at work).
posted by Rash at 8:13 AM on December 31, 2011 [1 favorite]

Another vote for email... or possibly Facebook, or other social networks. But really, I prefer email.

Transitioning to texting is nice too, but stay away from anything remotely cybersexy. Talk about your lives, get to know what he likes to do on his spare time... make a point of finding out what his hobbies are, what kind of food and restaurants he likes, and what kinds of things he finds relaxing, ideally away from the rest of the world, without a lot of entertainment or distractions... and then let him know you aren't doing anything on a day you have completely off/unscheduled... and ask him if he'd like to do _______.

Go on a ride into the country, and ask him to bring along a favorite CD, if he has one (you should bring one as well)... go to a quiet beach... or hiking... or to a picnic in a park... (bring a kite and stop by your favorite deli first, perhaps...) But the point is, go somewhere, do something together, and talk... ideally quietly. Simple and inexpensive is good... and less stressful, too! Make a nice day of it together... and, if all goes well, go to a restaurant that is both good and affordable afterwards. The idea being... build from quiet, relaxing outings, with moderate activity to situations that are potentially more lively afterwards, so that by the time you get to that restaurant... if you choose to do so... you're far more relaxed than if you had gone there in the first place.

So much about romance and solid relationships is built upon two relaxed people speaking to each other in soft tones, I find. Those are the moments that allow real communication, which you need to cultivate, if you find someone you like.
posted by markkraft at 8:39 AM on December 31, 2011

If he doesn't appreciate you being forward, perhaps he's not right for you anyway? Just ask him what he's up to, and if he'd like to hang out some time.

I understand where you're coming from here, but as others have said, clear communication is best. I've always wondered if I misread signals from women who seemed like they might be interested, but if they never said anything, I'd have to assume that they were not...because they didn't want it enough to say something. And while I may not be shy, I was always just a little too polite to not intrude where I thought I wasn't desired.

The worst he can say to you is no. In which case, realistically, you're not worse off than before. Rejection may hurt, but in the grand scheme of things, will later turn out to not be that big a deal.
posted by Strudel at 8:54 AM on December 31, 2011

Hmm. I'm a little surprised that people would advocate straight-up asking out a guy that a) you work with, and b) has apparently never spoken to you, except for answering you half the times you've said hi. I agree with headnsouth and wonder, if this guy wasn't so attractive to you, would you not find his behavior simply rude?

That said, if I were you* I would move really slowly. Keep talking to him in a low-pressure way every chance you get. Maybe, over time, he will become comfortable enough talking to you for you to get to know each other in a casual, office-friend sort of way. (This could take a long time. You say he talks to people in his department - do you know how long it took him to get to that point? Months? Years?) Then, if you think he likes you and you know he's actually single, straight, etc., you can start with asking him out for coffee. I just think that currently - even if he really likes you - if he's too scared to answer a simple work-related question or say hello after you've said it first, he will not respond well to a date invitation.

*Actually if I were you I'd do nothing, because I learned my "I really like him but he won't talk to me, it's like pulling teeth, aaah!" lesson years and years ago. In my case, it turned out he wasn't talking to me because he didn't like me, and he managed to find his own awkward way to talk to girls he actually liked, when he had to. But I understand how you feel and I wish you luck!
posted by DestinationUnknown at 9:19 AM on December 31, 2011

Its not rude to be a shy person.

I say you ask an intermediary.
posted by Ironmouth at 10:13 AM on December 31, 2011 [1 favorite]

Nthing facebook or email. I get what people are saying about how you don't know if he even likes you, but hey, he's shy, so are you, and that's sort of the point of asking someone out. If you talk to him so infrequently, it hopefully wouldn't be a big deal if he says no.

And Effigy2000, as a woman who has received that advice many times in my life, and often followed it - well, it's a huge pet peeve of mine because in my experience it isn't helpful to women to say we'll never be rejected, because then we're unprepared for it when are, and left very hurt wondering what could possibly be wrong with us that we're the exception to such an apparently universal rule. Plus it's a limiting view of straight men, who might have any number of complex reasons to say no while single. I prefer a worldview in which both men and women are intelligent and complex people who let a huge and often inane array of factors influence their decision making, so a woman asking out a guy is just as much a crapshoot as a guy asking out a woman under similar circumstances.
posted by fireflies at 10:54 AM on December 31, 2011 [5 favorites]

Asking in person is fine, but as others have mentioned make the proposed activity short!

Coffee is best, even if neither of you drink coffee.

Also finding some excuses to see him at work before all of this -- even if it's just to ask a simple stupid question -- will go a long way towards making him comfortable with you.
posted by Tell Me No Lies at 11:34 AM on December 31, 2011

Best answer: Fireflies is right. It's not a slam dunk.

I was a very socially awkward guy back in '93. I had been pining over a girl at work, so close friend let her know that I was very, very interested. I tend to act in a very childish, standoff-ish way when I'm nervous, so a trustworthy intermediary was the key. The girl eventually felt confident enough to corner me and lead me through the date-asking process but she stopped short of actually asking. We've been a loving couple ever since.

Try to have coffee with one of his friends and ask about him.
posted by bonobothegreat at 11:57 AM on December 31, 2011

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