Be confident. If you don't think you're very interesting, attractive or funny, neither will she. Spend a minute or two psyching yourself up. Think of yourself as the coolest, most interesting, most attractive man on the planet. Look the part. Act the part. Walk the part on your way over. It's not necessary to believe in yourself, but it is necessary to fake it well.
Don't dither. Spot your prey and approach her. Standing around too long will make you over-think things. Go with your instincts.
Have something interesting to say. She's heard that she's beautiful before. And yes, she comes here often. Say something she hasn't heard before. Tell her a story, real or imaginary. Ask open-ended questions. Keep her involved in the conversation. Asking her opinion is fine, but avoid controversial topics.
Compliment her. Don't fawn over her. Just give one, simple, non-obvious compliment. Make it specific. Women spend lots of time trying to look good. Telling her that you like her hair, makeup or outfit shows her that you're attentive and appreciative.
Create a false time limit. Don't stand around long after the conversation has died. Explain that you're with a group of friends, and don't have much time to talk. Give yourself an out, then leave while the conversation is still going strong. She'll be around the bar or club for a while. Even if she decides to leave, she'll come to find you if she's interested. Women like attention, but they love a challenge. Let her pursue you a little.
Don't invest too heavily in one woman. Talking to a woman isn't any kind of commitment. Your first date is the job interview. Chatting her up is just sending in your resume. You're saying "Here I am. I'm interested." Don't come off as desperate or needy. She's not the only one in the bar. Remember there's nothing wrong with chatting up several women in one night.
Walk away. Let it go. Go hang out with your friends. Have a drink and pick your next target.
Tips
- Wear an interesting accessory for her to comment on. Women notice small things. Giving her something to remember you by sets you apart.
- Always remember her name. Repeat it to yourself three times as you look at her face. Invent a mnemonic--no matter how arbitrary.
- Practice makes perfect. Talk to women often. The butterflies will start disappearing. You will become the charmer you've always wanted to be.