In general I prefer to game with women, as it is much more efficient. But occasionally I also go out with a wingman and that is fine, as long as we both understand the general strategies and work towards common interests.

Bragging

You should never brag about yourself, but feel free to praise and compliment your friend. Actually a wingman should always do it. You tell the ladies how cool your friend is, how interesting, how well connected, and anything else that can add value to him before you introduce him to them. Your wingman should do the same.

I get to the point of sometimes just throwing out there a comment like “I don’t have any boring friends.” or “My friends are so amazing, look at him!”

Help each other

It’s easier to create more conversation and interaction if, instead of meeting girls and talking to them only, you always introduce them to your wingman as well. You must be quite sensitive to figure out when to leave him alone with a girl and when to come to his rescue, but that is something you can easily develop with your wingman.

I would not hesitate to ask my wingman to pick up a woman at the airport, drive her to her hotel, or bring her to the party. I would ask him to wear a jacket or suit for that, and behave professionally. I would not hesitate to do it for a friend, and I have done that several times.

Some time ago a friend of mine invited a girl for a dinner out and he gave her the address of his building, on the 7th floor. When she got there she noticed that the 7th floor was the roof garden and I had set up a table there with cloth, wine bottle on the ice, everything right. Then while they enjoyed their drink I walked in pushing a cart with their meals, and I was wearing a suit. After dinner they went down to his apartment and I cleaned up and removed everything. That was like a gift to my friend!