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You don't have to run up to the woman the second she walks into the room or you may look over-eager, but you should try to talk to her soon after you lock eyes. Look at her, hold her gaze for a second, and then just walk right up to her. Sound easy? It's not -- not at first, anyway. But the sooner you get into the habit of acting like it's no big deal to talk to a girl you see, the sooner it'll become a habit. Sure, you may strike out sometimes, but she'll be impressed that you can see her and just walk right up to her instead of playing eye contact tag all night. Take a deep breath, maintain good posture, and hold her gaze as you walk up to her. It's all about mastering the confidence. If she sees that you're confident about approaching, she'll be more likely to want to get to know you. Think about it: what's the worst that can happen? The woman could reject you or she might have a boyfriend. Does that sound like the end of the world? A lot of guys are afraid of approaching women because they just can't think of what to say first. How about, "Hi, I'm Mark -- what's your name?" The girl will actually be more likely to be wooed and impressed by your ability to act casual and natural instead of you trying too hard to impress her with an elaborate pick up line or an overly-clever comment. Treat it like any other conversation -- except that this one has romantic possibilities. Look her in the eye, tell her who you are, and ask her name. If she's with friends, talk to them too, and don't make them feel left out. Once you and the girl start talking, you should try to touch her when the time is right. The sooner you can get yourself out of the Friend Zone and establish that you have a romantic connection, the better. If things are going well, lightly tap the girl's knee, touch her arm, or give her a playful touch on the shoulder. Keep it light and fun, or she may get turned off if you're moving too fast. Try moving a bit closer to her and see how she responds. If she doesn't pull back, then it's likely she's into you. Save all the serious talk for later. If you want to really woo a woman, then you have to keep things fun and light. To be playful, just don't take yourself or your conversation too seriously. Crack jokes. Tease her. Make everything feel lighthearted and stick to fun and easy topics, like your pets, a concert you went to, a ridiculous celebrity scandal in the news, or just anything fun and breezy. This doesn't mean you have to stop being yourself to act like a "chill" guy, but it does mean you should avoid the serious stuff off the bat. Though girls like to be asked questions because it shows an interest in them (more on that later), don't immediately start asking the girl a million questions or she'll feel like she has all the pressure to keep the conversation going. You're supposed to be wooing her, not the other way around. Your rule of thumb should be not to ask more than two questions in a row. You're supposed to be wowing her with your conversational abilities, not making her pick up all the slack. Many people like to ask a ton of questions to immediately search for common ground, panicking that they will have nothing to talk about. Well, don't worry so much about having things in common -- work on getting the attraction going first. After that, your common interests will come up naturally. If you want the girl to be interested in you, then you can't tell her the 50 most interesting things about yourself in the first 5 minutes of the conversation. Make her work for it. Don't be an open book, or she'll think that it's easy for anyone at all to find out everything about you. If you wait to dole out the important things about yourself, she'll feel more special and privileged when you do. Sure, you can talk a bit about your friends and family, but don't tell her all about your biggest regret, your dreams for the future, or your most traumatic childhood moment. If you keep things a little mysterious, she'll only want to see you more.
Approach the woman as soon as you can. Don't put too much stock in having the perfect opening line. Break the touch barrier. Keep things playful. Don't treat it like an interview. Don't tell her everything at first.