How To Ask A Lady Out If You're Shy

1. Remember that some girls, even if they are pretty, have very low self-esteem. Girls over-analyze way more than guys, and can take even the smallest thing in a bad way. If you are shy, just remember that any girl will be flattered just by you showing interest.

 2 Flirt with her a little bit. If you feel like flirting is not your strongest point, don't sweat it. Just make sure she at least has a chance to realize that you might be interested in her before you ask her out. It is a big thing to have someone ask you out, but if you have no idea they like you it is even more of a surprise. Even paying special attention and talking to her more can introduce the idea to her. A lot of girls are really shy and they sometimes will never tell you if they like you. So sometimes, you have to be the one to approach them.

 3 Find a good time and place to ask her out. Over the phone is good, but avoid e-mail or text messaging, which are too impersonal. Casual is the best way to go. Saying, "Hey, want to do something later?" is far better than detailing what you have carefully planned out.

4. Be confident. Unless the girl avoids you, she probably doesn't mind you, even if she doesn't outright like you. Girls are taught in society to be nice. If she says something like, "Oh, I'm really sorry, I was going out with friends that night," don't be put off. Ask only once again. If she gives another excuse, ask if she can make it another time; if she can't, she isn't interested.
5. Avoid having a friend with you. It almost always makes her nervous. A lot of girls will think you're pretty cool for being able to speak to them in private, by yourself.
6. Avoid having her friends there. It will make you nervous. Get her by herself. Enlist your friends to distract her group, or find out a time when she is alone.
7. Just do it! That's all you have to do. Just jump into it. If you like a girl and she may like you back just ask her. If you hesitate you may never build up enough confidence again. You'll never know if you don't try.
8. Even if you are not confident, act like you are. Girls love suave guys. Don't whip out a, "Hey Sexy, I'd love to get dinner with you this Friday," but be confident in yourself. Nervous guys aren't cool. If you are nervous and think it is a good idea (you are the best judge of the situation), tell her that you're a little bit nervous.
9. Avoid heavy compliments. It is okay to say you're nervous, but don't say anything too strong, like, "I'm so nervous because no girl so pretty has gone out with me before. It will make her feel weird. Coming on too strong on the first date is a big no-no. Even if she likes you, she'll feel slightly freaked out.