Rule No. 3: Respect the ratios
Your friend is talking to three women. You join. One of the friends seems to like you, and now you want to take her somewhere private, away from the group. Should you? No. If you do, you’ve left your buddy with the woman he wants—and her friend. In other words, you’ve left him needing a wingman. Wasn’t that your job? (However, if it’s just two guys and two girls, leave with the other woman if you can. We call that a win-win.)
Rule No. 4: Say what your friend can’t
Wait until your buddy goes to the bathroom to talk about his best qualities. For bonus points, don’t talk directly to the woman he’s interested in. Tell one of her friends instead, and wait for her to repeat it.
Rule No. 5: Do what your friend can’t
If your buddy is too direct with his girl, it might turn her off. But you can suggest one last drink to enjoy the view from his amazing rooftop. Or, if you know she drove there, explain an “emergency” to your friend and why you have to go, and ask his girl if she’d mind driving him home, since you were his ride.