Is it Bromance? How to Pick the Best Wingmen

When you’re out flying the -- hopefully -- friendly skies in search of a good woman, you’ll need a great co-pilot. Here are the traits he’ll need to have.

Meeting women is not a solo sport. For men, it's essential to work in teams -- typically two-man excursions with one man in charge and the other designated as wingman, whose primary role is to assist the "pilot." Whether the setting’s a bar or bookstore, a good wingman can turn a strikeout scenario into a successful sortie.

So what kind of guys should you recruit before suiting up for a mission? Well, when it comes to separating a green pilot from a flying ace, say our sources, a good wingman should be …

• Assertive As anyone in the game will tell you, it takes guts to approach women cold. "A good wingman will push his buddy to take risks,” says Stephen Simpson, Ph.D., who wrote the book What Women Wish You Knew about Dating. “He gets you to do things you wouldn't. He's the icebreaker, the cheerleader and the commiserator when you get rejected. He makes you go talk to that woman whom you think out of your league.” Think: Sydney Fife (played by Jason Segel) in the recent hit flick I Love You, Man.
• Similar (to you) No matter how bold your wingman is, if you don't click with him, you're probably going to crash and burn. Dr. Geoffrey Greif, a professor of social work at the University of Maryland, talked to 400 men and 120 women for his book Buddy System: Men and Their Male Friendships. Based on his research, he says, "Nerds don't like hanging out with jocks -- they find them intimidating and uninteresting. Masculine guys hate being thought of as gay, so they won’t hang out with effeminate men." In other words, your wingman should be someone you're comfortable with. While relative looks don't matter that much, he says, "men seek friends who have the same level of masculinity."
• Adaptable It's called "jumping on a grenade" -- the wingman act of talking (and possibly more) with a girl's friend, freeing up “the pilot” to hook up with said girl. But it's just one of many wingman duties, all tying into being adaptable to any situation. If, for instance, in the middle of the evening you decide to change course and go after his prospect, instead of your own -- your friend should go with it. If you introduce yourself and your wingman as traveling beekeepers (despite his potentially fatal allergy to yellow jacket venom) to spark the interest of a group of women, he should also go along with it. And if you make him pay for the drinks, he should still go along with it (because you’ll get him back later -- right?).
  
  "He has to understand you -- he has to be able to read you," says Greif. "Men don't like to explain things to a guy, so a good wingman will know when to get you to talk and when to not force you to." Perfect bromantic example: Butch Cassidy and the Sundance Kid. "They got each other’s humor," says Greif. A more modern bromance: John (Owen Wilson) and Jeremy (Vince Vaughn) in Wedding Crashers. 
• Male Contrary to conventional wisdom, women don't make the best wingmen. While on the surface, enlisting a female co-pilot seems like a good way to show you're "safe," it raises too many questions, says Simpson. "She'll wonder why you hang out with women. She'll think you don't get along well with other men. And she'll have questions about your relationship and history with the woman. The last thing you want is a quiet, mysterious female at your side while you're hitting on someone."

Greif agrees that men make the best wingmen, with different reasoning: "They will not press the guy to be too emotional or emotive. Men like being with men because they will not be pressed to talk about their feelings as much as with women."

The Ultimate Wingman
Put all those qualities together, and who do you have? According to Simpson, Vince Vaughn's character from Swingers, Trent, epitomizes the ideal wingman.

"He begins by encouraging you and offering advice. He pushes and guides you until, suddenly, he's no longer needed. A good wingman wants the student to become the teacher. He wants his buddy to reach the point where he says, 'Don't worry -- I got this.' It's the self-sacrificial aspect of male bonding. We can't die for each other in battle as much as we could a century or two ago. But we can still jump on a grenade now and then."