How to Flirt With a Woman at a Bar

Flirting at a bar is warmth plus a little play. When approaching women there, you make friendly eye contact, smile, tease her lightly about something small, and let her see that you are enjoying the talk and interested in her. You do not need smooth lines or a big act. You need to be relaxed, pay attention to what she says, and watch whether she is playing back. When she is, you lean in a bit. When she is not, you ease off.

Most men think flirting means saying something bold. In a bar, boldness without ease reads as pressure. Rushing in with too much intensity, standing too close and talking too fast makes a stranger nervous, not charmed.

Real flirting is lighter. It says: I like talking to you, and I want you to enjoy this too. Everything below serves that idea.

You cannot flirt with a woman you have not talked to. Walk over, say hello, give your name and ask something easy about the room. If she is open, she will answer with more than one word and turn a little toward you. That is your signal to start adding color.

She is likelier to be open early in the night. A woman who has been bought drinks and hit on for hours has her guard up by midnight, so an early hello and a slow build work better.

Eye contact does a lot. Hold it a bit longer than you would with a coworker, then look away first, calmly. Smile when something she says is funny or sharp. A small, real smile beats a big, practiced one.

Keep your body open. Face her, keep your hands visible, and do not cross your arms. Stand at a comfortable distance and let her close the gap if she wants to.

Light teasing is the heart of bar flirting. It works when it is gentle, about something small, and obviously friendly.

• If she orders a complicated drink: "That sounds like homework. Is it worth it?"
• If she says she is terrible at pool: "Good, that makes two of us. We can lose with style."
• If she tells you she is a morning person at a bar: "I am going to need to hear more about this lifestyle."

Smile when you say it, and then ask her something real. Tease something she chose or said, never her looks, her friends or something she cannot change. If she teases back, you are on the right track.

The best flirt is a man who is paying attention. Remember what she told you and use it two minutes later. "You said your sister is visiting. Is she dragging you to every tourist spot?" does more than any line. It shows interest in her, not in impressing her.

Keep your stories short and pointed, and do not just repeat her questions back. Ask one question, listen, and add one small thing about you.

Flirting should leave no doubt that you like her, and it should leave her every freedom to decline. A simple line does it: "I like talking to you. I wasn't expecting to meet someone tonight." Say it once, calmly, and keep going as if nothing depends on the answer.

If she steps closer, laughs, touches your arm or asks you things back, she is enjoying it. If she gives short answers, looks over your shoulder or turns back to her friends, she is not. Respect that quickly.

• Comments on her body.
• Standing too close or touching before she signals comfort.
• Talking over her or making every sentence a joke.
• Staying after a no, and following her around the bar.
• Pretending to be someone else.

After about five minutes of easy talk, tell her you have enjoyed it and ask for her number. If she says yes, great. If she says no, say "No problem, enjoy the night" and go back to your drink without a fuss.

Flirting is a feel more than a script, and feel improves with feedback. A Cold Approach Bootcamp puts you in a real venue with a coach beside you, gives live coaching on every approach, and reviews it after every set. It runs in Miami and New York. Group is three consecutive days at three students per coach, and Private is 1-on-1 for one, two or three days. A total beginner is welcome, and approach anxiety is the specialty.