So, at work this girl came in, and she wasn't very vocal/ stayed in the background while I talked to her boyfriend. He had a shit ton of opnions, almost too many for his own good. I gave her coffee, and was nice to her. But she was very very timid. I was wondering what would make her so timid? Her boy seemed nice. Tt was like I had to ask if she wanted something to drink, she wouldn't ask for it.

And on to my current interest who is also shy. So, I heard my boss talking to her on the phone about getting her braces off. I was wondering would it be wrong to comment on the fact, or say something about it like " Whoa! smile again" and then make a comment about her braces? or would that be too forward, and make things akward.

i think even shy girls want to be complemented for having their braces off. But in general with shy girls ya just gotta get in their good graces and treat them right. Generally they are shy because they are self-conscious, you gotta tell em all their good qualities and then your in.

I tell shy girls to pull their heads out of their ass; they're not protecting anyone, especially themselves.

Sure, they usually cry and I don't get laid, but I just saved the next guy all the trouble of dealing with her insecurities.

I'm not sure if I'm joking, or not...I know I've made quite a few girls cry from saying that...but I don't know whether or not it was effective. Hopefully, by how easy I recognized their mental state, they'd realize that the kind of people that attack insecurities would see them just as well.

I also wonder if I've ever driven someone to suicide by accident. Oh well.

First girl probably didn't want to talk to you.

Second girl, who doesn't like compliments? Pointless.

First girl talked to me, and was intent on hearign what I had to say on the convosation. I didn't really like her, and it kinda pissed me off she was so shy.

The second, Well. I am taking small steps considering She is the sister of a GOOD friend.

Bushy's a kiddy fiddler.

OP: Tequila.

I didn't really feel like reading your post, so I'll go with assumptions . You need to make her feel comfortable with you and in the given environment; if she can trust you, then she will open up to you.

she is my boss' sister. Thats why. But I am tight with my boss. Soo. yea, she is also kinda a co-worker

Casually talk to her, get to know her better at work and then ask her out somewhere?

Just lob your cock out in front of her. If she opens her mouth to complain, shove it right in.

On a serious note, try making her feel special in front of other people. Chick's like that.

If you can follow that up with a good dose of humour, a bit of playful bantering, and making her feel special, you'll be doing pretty good.

But try the first one. Let us know how you go.