I'm shy, so I generally like it more when girls take the initiative to spark conversations or, show interest. If you show interest, being that he's not blind, he'll see it and react appropriately. If he likes you in return, his shyness should have no relevance to his interaction. While it may be limited, he'll mean it.

Get to know him slowly. When you know him enough you'll see he'll drop all the barriers and will feel free to be open with you. Then you can make your move.

Shyness often develops out of insecurities, maybe he doesn't feel very confident in himself. Drop a compliment here and there to him, start conversations with him. Chances are he'll become more comfortable with you if you start to open up with him. If you're unsure about talking to him more, start with a simply 'hi' when you see him, and eventually build until it seems normal for you two to be talking. Maybe try hanging out with him if possible, if he realizes you have taken an interest in him, then he might let down his walls and become more open around you. Just take it nice and slow, don't rush anything and see how he reacts to you as you become more social around him.

Like Andrew, I'm shy and usually prefer the girl to make the first move. After that I'm
fairly open with her.

Luke

I've had experience of dating shy guys.I find them attractive as opposed to up-themselves confident guys.I always make the first move & it usually works.I act a bit shy & I tell them I really like them & comment on some quality they have which I like.I also tell them I know they are shy & that I amto & I ask them to go out with me.
It hardly ever fails.Go for it.

Dont listen to the emo...

Anywho don't give compliments chances are that will just choke him up or somthing. Best bet is to crack a joke or two with him or talk to him when hes in a more layed back scenario. Dont be corny cheesey or desperate. You got the pussy so the wittle boy will most likley fear you. Dont make him think of the pussy. Or you could tell him about your cum swallowing habbit and refer him to that other thread ya know??? GL

I think puberty makes us shy. But you're talking about older guys I think.

Anyway, once I have more confidence about myself I wont be so shy.

So the others are right. Go slowly with this guy and try to get him alone, not when there are other around. He might feel more comfortable and less embarrassed then.

Well for one do your best not to embarrass him. Most guys are shy and actually like it when the girl goes after them . Guys don't get that very often because of gender roles that society has implied as far as dating goes.

You can try subtle hints and maybe even flirting. Write him a letter or send him a message online or a text. Whatever you do , just talk to him in private or one on one instead of in front of a lot of people. The last thing you'd want to do is embarrass him and scare him off .

Don't listen to this kid, I know it's quite obvious, but I don't know your state of mind, and I'm hoping you have enough logic to ignore the troll.

Anyways, I'm quite shy myself. I do not, and will not greet someone I do not know, even if I like them. There is a guy at my school I like, and I haven't said a word to him about it for the past 6-7 months that I've liked him. Yeah, it's my loss, I know, but I'm too shy. Your best bet would be to approach him, obviously don't enter his comfort zone, just stand back a bit to give him room to breathe. Start a conversation on the whereabouts of your location maybe, or a movie you could've just seen, or anything of the sort. Maybe after a little while drop a few hints that you're interested in him, and maybe tell him he's cute or something of the sort. Just take it slowly, but progressively, and don't push too far if he's that shy. I know when people pry too far with me, I get sorta scared or creeped out, I prefer my distance until I'm comfortable being around and speaking to that person. Like, I was at a party this weekend, and this girl sat on the couch next to me and tried cuddling up against me, I completely ignored her and stared forward. I didn't like it the slightest bit, it was completely awkward, and irritated me.