It sounds like a question of self-confidence, and it's more YOU rejecting the opportunities that come to you, than they rejecting you. You have to consider, "What's the worst that can happen?" She says, "No"... Does that mean for THIS date, or no, she's not into me? You COULD ask if she would be interested at another time, but if she says no again, she's not into you. Is that really so bad? I mean, you point out that you're not unattractive (your ego seems to be ok, here! ;-) ), but even those who are sending signals that they may be interested you have problems approaching. Are you sure of the signals? or not? Breaking the ice in a "stranger" circumstance is difficult for all. One thing you want to do is make sure you talk about HER, not you. People, though they may protest, want to talk about themselves. Find something you have in common to talk about. "Lines" (pickup lines), especially inane ones, do not work... In fact, they could turn the "target" off quicker than if you spit on them when you talked. But, again... What's the worst that can happen? A "No?" So what...? That's not gonna kill you is it? I bruises your ego a bit, but if you toughen up that ego just that bit, then it's not gonna hurt. It comes with practice and success. ;-)

dude....ask on out and if she says no ask another. Besides chicks like confident guys

I believe that rejections are not about you. They are about the chemistry, vibes, mind script, etc., of the OTHER person, and you have no way of knowing what that is. When I've rejected someone, whether it's a coworker, in a club, or whatever, it's about the mold I need the person to fit for me. It doesn't really have anything to do with them. It's all in my head. So figure that the ones that reject you . . . it was meant to be and it was not a good fit for you.

Just go up to one of them and ask them to lunch first. It's the easiest way. Lunch is an unofficial type setting. It is relaxed and uncomitting therefore she does not feel obligated. If it works out and she is laughing by the end of lunch ask her to do it again. It is easier for the woman to find out if she likes you in a non-stressful atmosphere. Therefore it won't be rejection if she decides to leave. She is just saying we might not be right for each other. That is not rejection. See simple logic will get you over it.

Be yourself and talk to them. Women are people too. If you don't try, you'll always be wondering "What if?". Life's too short.

I'm hesitant as well, so I know exactly how you feel. I've been there, time and time again. So I decided to say to hell with it, what do I have to lose? So what did I do? I go and approach a lady I've fancied for a while. I got rejected. Brutally. And I'm not a bad-looking guy, either. So I asked out another girl. We had a couple of dates, and I got rejected again. So a couple of weeks ago I asked out another girl, and was... you guess it, rejected (albeit obliquely). So my point is, after a really bad rejection (and I bet you've had none worse than mine), you start to really not give a crap. You get a thick skin, and the rejections just kind of bounce off. So what if the lady in question doesn't like me? Yeah, it sucks, but it's better that I get the chance to find out and move on RIGHT UP FRONT than be trapped in a bad relationship for an extended period of time with someone who's just using you (and that's happened to me too). So get out there, take your licks and get tough. If lady XYZ doesn't like you, to hell with her. There's likely someone who WILL like you right around the corner. Go and get bruised, it's the only way to do it.