From A Woman's Perspective Top 5 Wingman Rules

This past weekend, I spent most of my time re-honing my Winggirl skills for some single friends while my boyfriend was working, so I got in a little time ; skills that had been going mostly dormant since college.

Now, being a wingman or winggirl is a delicate endeavor. I have been winggirl for other female friends, for male friends, etc. and there are several rules that hold fast regardless of gender or sexuality. Obviously I have never been a guy winging it for another guy, but I can only assume these Top 5 rules are universal:

Have Another Ride Home: The scenario: you’re wingman for your friend. Your friend is also the DD. This makes absolutely no sense. As the night ends, your friend is going to be stuck with the super-awkward position of leaving to drive you home and then coming back to the bar, or you’re going to be stuck waiting around for your friend and the paramour to figure out what they’re doing and exchanging numbers so they can drive you home. Be smart and either book a cab or a third friend who can come get you.
Don’t Be Sloppy: This applies for guys and girls; I have that wonderful friend who once got so drunk she wandered into a busy road and got hit by a police car, needless to say, she makes a terrible winggirl. Every guy also has that friend who gets really drunk and takes his shirt off and tries to start a fight or says something stupid to the bartender. Don’t be that guy. And that applies to being a wingman and just in life in general - don’t be that guy. Remember, Stray Monkey is for Respectable Men.
Be Prepared to Dive on the Friend Grenade: More likely than not, your friend’s target has a Goose to his/her Maverick along for the ride too; and if you’re lucky, they’re also in a relationship and are trying to stay out of the way and be a good friend. Be prepared to make annoying small talk with this person for awhile, because it’s probably going to be between this or talking to no one, or playing another game of Angry Birds on your phone for the next two hours. Have some innocuous topics to talk about to kill the time; like: how’s the local football team doing this year? Or, Seriously, how funny is Will Ferrell? Are these questions stupid and annoying? Yes. But on the off chance your friend and this Friend Grenade’s friend end up together, you both will end up giving awkward wedding toasts in three years, so you might as well resign yourselves now.
Do Not Lie: We live in an era of Facebook, Twitter and stalker-phones, if you lie, you will get caught eventually. I once had an out-of-town friend visiting, who gave a fake phone number to a guy at a bar, and when he asked me if that was really her number, I lied for her. When he tried to call her and figured out it was the wrong number, he was clearly let down. However, what neither she nor I realized at that bar, was this guy was MY next-door neighbor, and I got to spend the next ten months of my lease riding the elevator awkwardly with a clearly angry dude, while she got to go home after her weekend of visiting.
Do Not Challenge Your Wingman: Don’t challenge your friend’s masculinity, athletic ability, or intelligence when being the wingman. This is key; never make yourself look better than the guy that you’re trying to help. A good wingman always puts his captain first.

Good luck, gentleman.