Remember that a lot of girls or ladies, even if they are pretty, have very low self-esteem. Girls and some ladies, stereotypically, 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 or lady will be flattered just by you showing interest.
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 and ladies 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 and overcome your shyness.
Find a good time and place to ask her out. Over the phone is good if you are shy, but avoid e-mail or text messaging; these methods 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.
Be confident. Unless the girl or lady avoids you, she probably doesn't mind you, even if she doesn't outright like you. Girls and ladies 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.
• Even though you are not confident and are shy, act like you are not shy. 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.
Avoid having a friend with you. It almost always makes ladies nervous. A lot of girls will think you're pretty cool for being able to speak to them in private, by yourself.
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.
Just do it! That's all you have to do. Just jump into it. If you like a girl or lady 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.
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.
Tips
• Look for hints she may give that she likes you. Like if she twirls her hair, or smiles a lot, sometimes she even gives you 'the eye' you'll know what that look is if she gives it to you, that's all flirting.
• Be mature to show her that you care. Be funny, kind but serious at the same time. When asking, don't come on too strongly. But you could just tell her that you like her.
• You probably want someone who will give you tips and confidence, like another friend, even if they are your opposite gender. Sometimes it's even better to have the opposite gender help you. If you ask her out and she doesn't like you, then you never had a chance to begin with. That's why you should find out a little about her, maybe start just trying to be friends.
• Make sure you're alone. It's best if you're in a quiet place so no one can suddenly shout at you because it might make you nervous and say something mean about her. Then your relationship would probably be over.
Warnings
• Do not obsess about one girl, you will probably get depressed if she turns you down.
• Don't pressure her - this will only cause her to be nervous around you.
• Tell her yourself. If you have a friend do it for you, you'll seem like a coward. If you just can't get up the confidence to tell her, leave her a note and at least do that yourself.
• Be confident, don't back down and chicken out.
