How to Pick Up Older Women at a Bar

Pick the right bar first, then talk to her like an adult. Women in their thirties, forties and older mostly skip the loud bars full of twenty-two-year-olds and spend their evenings at wine bars, hotel bars, restaurant bars and calmer lounges. Walk up with a relaxed hello, tell her your name, and keep the talk on her, the room and the night rather than on the age gap.

The single biggest reason men never meet older women at bars is that they go to the wrong ones. A sticky bar with a beer pong table and a DJ playing to college kids is not where a thirty-eight-year-old lawyer spends her Thursday.

Look for these instead:

• Wine bars and cocktail bars with real seating.
• The bar area of a good restaurant around dinner time, where women wait for a table or eat at the counter.
• Hotel bars, which mix travelers with locals out for one good drink.
• Bars with live jazz, acoustic sets or a pianist.
• Neighborhood places early in the evening, before the younger crowd arrives.

Timing matters as much as the room. Many older women go out after work, meet a friend or two, and are home before midnight. Seven to ten in the evening is your window, so a man who rolls in at eleven has already missed most of them.

You do not need to read minds. A few plain signs tell you most of what you need to know. She is looking around the room rather than into her phone. She smiles at the bartender or the people near her. Her body is open to the room, and she has a free minute because she is waiting for a drink, a friend or a table.

A woman deep in a long catch-up with her best friend is telling you not now. So is one with her back to the room. A woman sitting alone at the bar with a glass of wine after work is often the most open person in the place, because she chose a seat where strangers talk.

Keep the first line short and normal. "Hi, I'm Dan. That looks better than what I ordered. What is it?" is enough. So is "I had to come say hello before I left." You are not trying to be clever. You are showing her that you are relaxed and easy to talk to.

Then give her one thing about you, so the talk does not turn into an interview. Mention where you came from tonight or why you picked this place.

Leave her age out of the opener completely. "You look great for your age" is an insult wearing a compliment's clothes. Jokes about cougars land worse. If age comes up later, answer honestly and move on.

An older woman has usually dated enough men to tell within a few minutes who has a life and who is still figuring one out. She is less impressed by bravado and more impressed by a man who is settled, direct and fun. a dating coach's view is that a younger man can date older women, as long as she does not see him as a little boy. A man who is plainly in charge of his own life rarely hears an objection about his age.

Ask about things she cares about: her work, the trip she just took, the neighborhood. Listen, then add your own story. Tease her lightly once she is laughing. If you are younger than her, do not apologize for it and do not make it the topic. Confidence about your own life matters more to her than the number on your license.

Most of the turn-offs are forms of pressure:

• Standing too close, talking over her friend or hovering after she has turned away.
• Buying round after round, which reads as trying to purchase her time.
• Getting drunk while she is on her second glass.
• Treating her as a conquest or a fantasy instead of a person.

A short answer and a look back at her friend means the conversation is over. Say "Nice talking to you, enjoy your night" and go. Bars like these have regulars, and a gracious exit is remembered.

Older women tend to have full calendars and work in the morning, so be clear and specific. If the conversation is good after fifteen minutes or so, suggest grabbing a table together. Or ask for her number with a real plan attached: "Let's get a drink on Thursday. There's a wine place near me you'd like." A vague "we should hang out sometime" gets a polite nod and nothing else.

Reading a quieter bar, opening without pressure and leaving well are skills you build by doing them with someone watching who can tell you what he saw. A Cold Approach Bootcamp is fully in the field in Miami and New York, with night game in real bars and lounges mixed with daygame to suit you. Each training day is two four-hour blocks, with live coaching on every approach and feedback after every set.

Group runs three consecutive days at a 3:1 student-to-coach ratio. Private is 1-on-1 for one, two or three days. There is no skill floor, approach anxiety is the specialty, and you leave with a written practice plan for your next night out.