It doesn't have to be this difficult.
We all remember the buddy system from grade school. When you'd go to the ocean, you'd have a buddy. When you'd go to the museum, you'd have a buddy. And now that you're old enough to hit the bar scene, you should still have a buddy.
You, my friend, need a wingman.
There you are with a friend, seated at a bar. You put out "the vibe," as you casually make eye contact with a ridiculously hot, seemingly hygienic female.
Your buddy, whose girlfriend is thankfully home for the evening, encourages you to approach. He reassures you that he's a few steps away in case disaster strikes.
You walk up to her with high hopes, employing the confidence that only four shots of Maker's Mark can provide. You offer to buy her a drink. But when the pool of standard chitchat/bar talk dries up, you find yourself at a loss for words.
Terrified and annoyed that your game has once again failed you, your mind reels as you reach for topics. You panic, unsure of what to say next.
However, just when you thought the situation was doomed, your buddy sidles his way into the action. With a mix of Sinatra charm and Dino comic relief, your steady, reliable, trustworthy wingman has successfully resuscitated the conversation. As you are reborn, he quietly slips away.
Your supportive third wheel, a wingman is the guy stopping you from saying or doing something stupid. Typically a close friend, he should possess both a good working knowledge of your strengths and an impeccable talent for masking your weaknesses. He's your sidekick, and depending on the success of the evening he could also be your superhero.
There are two things I know never to leave home without: my American Express card and my wingman. Without these two things, the chances of a hookup are practically hopeless. But just like choosing a credit card, choosing a wingman requires some serious thought and planning.
The main thing to consider is personality. You definitely need someone who can carry a conversation, but you don't want someone who will steal your thunder. You need a guy who knows you well enough to recall the time you spent at the soup kitchen, but who's also smart enough to leave out the fact that it was for 50 hours of court-ordered community service.
In addition to making you look more Brad Pitt than Brad Garrett, the wingman must also keep a close eye on the social lubricant situation. If the glasses look dry, he's the guy who will trek over to the bar and order the next round. (It is proper etiquette to pay for your wingman's drinks that evening. This also ensures his loyalty and support for future outings.) This time alone surreptitiously provides you and your lucky female subject with the appropriate amount of alone time. The wingman's absence is simply a test to see if you can handle the situation without your trusty insurance policy.
If all goes well, upon his return, he gets the nod and searches for an appropriate exit in the conversation so you can exercise your "closing" techniques.
If things don't go so well during his minutes-long excursion, you know that the chemistry isn't there. A good wingman should have full knowledge of the signals in play: a single nod for "you can leave now" or a double nod for "we both can leave now." Not to mention, the mutually convenient triple nod for "stay, she's got a friend," or the extremely rare, yet somewhat selfish quad-nod for "she's got friends, but they're all mine."
Once you have found and trained someone to serve beside you as wingman, practice your routine as much as possible. The only thing more embarrassing than an idiot with nothing to say are two idiots with nothing to say. Unfortunately in this case, two idiots do not cancel each other out.
When used correctly, the wingman can be extremely valuable and the system is relatively easy to perfect, based on the intelligence and sobriety of the parties involved. He is your safety net, your backup plan in case of a sour evening. He is the Aaron to your Moses (hopefully not the Cain to your Abel).
And if all this still doesn't work and you find yourself totally hopeless, unable to meet a woman in a social situation, wingman or no wingman, fear not my troubled friend -- there's always the option of a shidduch.