How to make friends with a shy person

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So I'm finding myself in an odd predicament...I'm shy, but not as much as I used to be, and I've always had problems becoming friends with girls (I'm a girl). I grew up a tomboy and turned into a geek. I can manage in a conversation about fashion, makeup, guys, etc, but it's hard and I hate it. I get along great with guys though. I'm so much more comfortable around them, and they around me - I think I've always been just 'one of the guys'. My situation now is that I'm actually making real friends with some other young women, but now it seems that guys won't talk to me, one in particular. This has never happened before. Guys and I just click, so I'm not entirely sure how to approach a guy looking just for a friendship, or even just as an acquaintance. To add to the problem, he's shy towards me. He acts fine towards everyone else, but he becomes super awkward around me (and maybe girls in general, but I'm not sure). He, myself, his sister (who I'm friends with), and another friend of ours (a guy I grew up with and have no problem talking to) all sit together at church. I've known all of them for over 10 years, but never talked to him really before, but it's not like we don't know each other somewhat and he's good friends with my brother. He responds when I talk to him, initiates conversation only when it'd be incredibly impolite not to, but it's quite obvious that he's so very awkward around me - to the point of acting like I'm not there when I am literally right beside him. I know enough about him to know he's not being rude and I really don't think he just doesn't like me as a person, so what gives? Should I try to break this shell a bit so he'll stop being so awkward, give it up and let him talk only if he wants to, or chuck something at his head (I'm leaning towards this option)? It drives me a little crazy for people to be more shy than me, so I have a habit of breaking people out of their shell (which often just makes everything even more awkward...), but I've never been in a situation quite like this before. Any advice guys? Should I leave him alone and bear the awkwardness? The worst part is I'm sure I've acted like this before, but I still have no idea what to do :-/

~K

I think he likes you and I do think he is shy around girls (excluding family a.k.a his sister)...
I think you have to use a soft voice when talking to this guy. Not whispering but very soft as if you are talking on the phone when you don't want others to hear in the next room.

Hm, I never thought of that. When starting conversations with new people I usually just default to being upbeat and perky so people will think I'm friendly. I never really thought of approaching it by just being myself haha! I'll have to try this next time I see him. Thanks

~K

Just act like it doesn't bother you at all, like you don't notice his awkwardness. Keep initiating and interact as normally as possible. Don't show any signs of rejection or being annoyed or anything else he might evaluate as being rejected.
If you do that for long enough, I'm pretty sure he'd become more comfortable around you.
At least that would work for me.

I find it easy to be one on one with them and don't call them out around everyone they get embarassed and talk about anxiety ect and they seem to appreciate your understanding of what they are going through and they seem to fit in more.

Except normal for me is working off the other person. I take their lead so to speak. I can't do that with him because he doesn't give me anything to work with, which is why it's so frustrating and difficult.

I'm trying to not show my frustration or point out his awkwardness, which is a little hard because I can be so blunt. I would hate to make him feel bad though, especially since he is such nice person.

~K

As a formally shy guy, I can totally relate from his perspective. Most people I've met seem to view me as nice but due to my autism it took YEARS for me to go above and beyond simple questions when it came to "conversation," so a lot of people viewed me as either "nerdy," "boring," etc.

I've known girls who got frustrated with me because I gave them nothing to work with in conversation. Looking back, I choose to build upon those experiences and work towards bettering myself instead of repeating past mistakes.

I've known girls who I know genuinely liked me, but had nothing to work with and so the friendship stayed roughly the same. But I kept moving on til I became something of a conversationalist, and now I don't look like an nerd at least.

Please, DON'T say he's awkward to friends, or to his face. All that will do is destroy his nascent self-esteem. I've had girls say to my face how nerdy or shy I am, and it wasn't pretty for me afterwards.

Respect the fact that he's nice to you and that he respects you. Overtime he'll become more social(probably) and even if it doesn't work out, you'll build up his self-esteem. I know that kinda sounds weird, but it would be a nice thing to do for such a shy guy.

Hang in there, and maybe he'll end up opening up to you socially.

This is something I have to work on, because I'm pretty blunt and almost rude when I don't intend to be at all. I've mentioned it to my brother and a good friend, because they're both friends with him, but I know neither will say anything to him about it and I only spoke to them for advice. My brother is convinced the guy's in love with me, but I really don't know how you can even like someone when you've never had a conversation with them! Guess I'll just wait things out and see and just be nice

-K

Also, I don't think he's autistic (though probably INxx on the MBTI), and I know he's had girlfriends before and girls as friends, so that further confuses me as to why he would be shy around girls now.

~K

Just FYI, I've had a girlfriend before and also have had girls as friends in the (recent) past.

He probably might still be autistic. He's shy because he may still have trouble relating to people due to his autism, despite his good fortunes with having girlfriends and whatnot.

Just because someone is shy/has autism, doesn't mean that girls won't still want to be his friend and/or be his girlfriend.

Sure, I had trouble relating to my girlfriend-I was very shy, and had trouble having complex conversations(I kept them very simple), but it worked out for a time.

Looking back, I wish I was as social back then as I am now. Oh well.

Dude likes you.

Allow Red Dwarf to explain:

[youtube]http://www.youtube.com/watch?v=a3t3IKlXqFU[/youtube]

That almost made me LOL thewhitrbbit, which would've been bad since I'm at work!

While I like all the self-esteem boosting, I really don't think he likes me like that (and I'm assuming y'all mean in a more than friend way). I don't see how he could since he hardly knows me except my association (granted, I do know a decent amount about him and only by association). I just don't see why he would have any reason to. Nor do I want to have anything more than a friendship with him, or anyone else right now.
He is quite attractive and the type of guy that most girls swoon over. A friend of mine used to work with him and she said that when he left the job all the women were so sad basically because their eye candy left. He doesn't seem to like the attention though and I wonder if he's reserved with women because he doesn't want to give the false impression that he's interested since he knows women fall for him easily.

~K

In his mind:

[youtube]http://www.youtube.com/watch?v=QJO3ROT-A4E[/youtube]

Ok guys for real, you need to stop making me nearly burst out laughing while I'm at work!!

In all seriousness though, I guess I'm not as good a judge of men as I thought. Any none music answers as to why someone would like someone they've never talked to? Maybe I'm just too logical and not emotional enough to get it.

-K

Love is by nature, illogical.

He might know a few things about you, and think your pretty.

When I think about a girl, I ask myself "Based on what I know about her at this moment, could i see myself going forward?"

It sounded like he's hung out with you before though.

If you count being in each other's general area at various times 10+ years ago then yes, we've hung out. I doubt we've said more than hi until the past few months. He is good friends with my brother and a couple other mutual friends, but I can't imagine me coming up in conversation more than in passing.

If y'all really think he's interested in me maybe I should just more or less ignore him for now. I really am not looking for a relationship right now and I hate leading people on. My obliviousness combined with wanting to be friends with guys usually ends up in disaster. :/

-K