How Do You Find a Wingman?

Start with the men you already know. Ask the single friend who likes going out, the coworker who talks about meeting women, or the guy from the gym who is always up for something. Then widen the circle: join a sports league or a group activity where the men are in the same place as you, and ask one of them to come out on a Thursday. If nobody around you will go, a coach who goes into the field with you does the job and gives you something a friend cannot, which is feedback.

A good wingman matters because he makes going out easier to start. A bad one gives you an excuse to talk to him all night.

Most men have two or three friends who would say yes if asked directly. Send a plain message: "I am going to practice talking to women on Saturday night. Want to come? You do not have to do anything but be there and be fun." Most men who are single want that invitation and do not know how to make it themselves.

a dating coach says it is often easier and more fun to go out with a wingman, and that it is fine to go out with a man younger than you. Age matters less than whether he shows up, wants the same thing and handles himself well with strangers.

Single female friends who like to go out can also work as a social wing, as long as you are not dating them. They get you into conversations and introduce you to groups.

Men who are open to this tend to be in a few places. Co-ed sports leagues, running clubs, climbing gyms, networking events and any evening activity with a mix of people. Talk to men there before you ask them to go anywhere. After two or three conversations, ask them to grab a drink after the event, and from there suggest going out some night.

You can also use the venue itself. A busy bar early in the evening often has two men standing together and not talking to anyone. Go over, say you are trying to meet people, and see what they say. Some will turn out to be the wrong match, and some will say yes straight away.

A wingman who has not agreed to anything stands next to you and watches. Fix a few simple rules before the night starts.

Decide who opens first. Decide what a signal means when one of you wants to leave. Agree that you will not talk to each other for long stretches, since the whole point is talking to women. Agree that if one of you gets into a conversation with a group, the other helps with the friends instead of competing for the same girl. If there is one woman you both like, the man who spoke to her first keeps her.

A good wing will talk to the friends so you can talk to her. He will give you room, keep the energy up and pull you away from a conversation that has gone flat. He will also tell you the truth afterward, kindly. "You looked nervous in that first set" is more useful than a pat on the back.

A bad wing talks over you, steals your target, makes fun of you in front of her or spends the night on his phone. If one night goes badly, say so directly. If the second night goes the same way, find someone else.

You will meet men who love to discuss meeting women and never actually approach anyone. Go out with them once and you will see it. Spending an hour on a bar stool analyzing a woman is not the same as walking up to her. Pick the men who stand up and move, even when it is awkward.

The most useful thing you can do is meet many different men over time. Experienced guys show you openers and styles you would not have tried. Newer guys remind you that everyone starts somewhere. Both help.

Some men have nobody to ask. Their friends are married, live far away or are not interested. That is a real problem, and it is the reason many men never start.

In that case a coach is the cleanest answer. On a Cold Approach Bootcamp in Miami or New York, a coach goes into the field with you for two four-hour blocks each training day. The coach watches your approaches, gives live coaching on every one and adds feedback after every set. Group is three consecutive days at three students per coach, so you also meet the other men training beside you. Private is 1-on-1 for one, two or three days. The days mix daygame and night game to suit the student, and you leave with a written practice plan you can take to your next night out with whatever wingman you find.