How to overcome shyness when speaking to a guy?

Don’t view him as a potential boyfriend, as you say, you’re not usually shy in a non relationship scenario, just chill.

I feel bad for you. And I don’t know if anything I suggest will be useful. This is a really tough situation.

Are you aware of your feelings when this happens? Do you freeze? Does your brain stop working? No thoughts come to mind?

Do you feel like you will make a fool of yourself? That other people will find out? That your reputation will be ruined with everyone?

I used to be afraid to ask a woman out because I felt sure she would say no and then tell everyone what a loser I am for deigning to ask her. So you can see it was a pretty high stakes thing for me. I could talk to the girls, though. I just never asked them out.

Anyway, I can tell you that most of the things you think might happen, probably won’t. Usually people are nice. And you might even just say that you are shy and have a hard time talking to guys you don’t know that well. It isn’t because you aren’t interested. It’s just that you have a shyness thing. Hopefully he’ll bear with you until you feel more comfortable with him.

That way you kind of tell him you are interested in him in a back door way and buy time to get to know him. It shouldn’t be a big deal if he’s also interested in you.

Another thing that makes sense to me is that if you really are interested, then you probably want to know whether he is interested or not as soon as possible. So you might as well speak up and see.

However, if you stay shy, you can drag it out a long time without knowing. This way, you can imagine something might happen and you can play this game in your head. As long as he hasn’t said no, you get to imagine a potential future.

I used to play that game. I’d never make anything explicit because I was convinced that when I did, I would be told no and the game would be over. I didn’t do this consciously. This is just my later analysis. I would just drag things out in an uncertain state because while that happened, I could imagine a nice future. As soon as I asked and she said no, it was over. No more material to fantasize about.

So you may be doing that to a certain extent. Just something to think about. If you are, then it is a self esteem issue, and therapy might help you start feeling better about yourself. That will make it easier to talk normally, without feeling the situation is so fraught with peril.

Well, there’s at least one argument in favour of not worrying too much. At least you’ve got the advantage of being a girl. Shy girls are cute. ;)

Also, what @ucme said. Are you like this around all guys, even ones you’re not into?
Maybe you just need some casual guy friends, guys that aren’t available for dating, just to get used to talking to guys.
Even flirting will become less difficult the more you practice it.

No I’m definitely not like this around all men. Two of my best friends are guys. It’s only with guys I’m interested in.

Would it help if you told your friend and they told the guy that you like him? Maybe then he could initiate the conversations more and help you feel at ease, and he would realize that you’re not being rude when you’re quiet.

I see. That’s good.

Well, I’m hardly an expert on this, but I’ve been in a gender-inverted version of the same situation – still am, to some extent – and I’m a bit further along in the process of deliberately growing out of this.

I don’t know of any tricks besides just trying it until you start learning. It seems to me that what you need is to get used to the idea that you don’t really have all that much to lose.

What exactly is the worst thing that could happen? Try to imagine that for a moment, but don’t exaggerate, be realistic about it. Would you be ashamed? Would the guy lose interest? How long do you expect it’ll take you to get over the embarrassment, and how difficult would it be to find another guy you like?

Maybe, just for practice, go to a place where nobody knows you, then go flirt with some guy and do it wrong on purpose, just to see what happens.
If it’s too much bother to do that in real life, try the internet, it’s easy enough to find random strangers there.

Come on out to my place sugar and madam Coloma will teach you how to intimidate men with your wit and verbosity. A short 3 week course in how to charm the pants off any guy in 2 hours or less. Yes, YOU can have him at ” hello.” lol

On a serious note, good advice so far, yes, do not view him as boyfriend material, just be yourself and let things unfold without contrivance.

Practice, practice, practice! Look them in the eye and ask questions. Be interested when they answer. Smile.

LOL, maybe you want to ask your BF for advice?
http://www.fluther.com/156097/i-cant-be-affectionate-with-my-boyfriend-what-should-i-do/