The art of being a good wingman is simple, yet essential. A good wingman must be an encouraging and honest friend, all while maintaining a nonintrusive distance.
The first step is to assist your friend’s scouting out the prey. Wherever you might be — out at the movies, shopping downtown, or even in the caf — look for a group of guys or gals. In a larger group there is a larger chance there will be someone with whom you’re friend will click. Avoid people who are alone, no matter how attractive they might be. They either want to be left alone, or nobody else wants to be around them. Then there is the worst case scenario, they are waiting for their boyfriends or girlfriends.
For the second step, once a promising group of young lad or ladies had been scouted, it is your job as the wingman to bear the burden of breaking the ice to alleviate any of your friend’s anxieties. There needs to be some degree of obviousness in your approach: from saying “hey my friend over there thinks your cute” to just straight wearing a t-shirt that reads “Wingman.”
Note that it needs to be established that this encounter is not for your health, but for that of your friend. Being obvious is okay, and it is better that you embarrass yourself being the bold one, than your friend embarrassing him or herself being overly flirtatious.
After having started up a group conversation, step three is to take a break to have a personal pow wow. Tell the group you are talking to that you have to run to the bathroom or grab something from somewhere that is anywhere but where you are. You need to take a break with your friend and review that situation. Talk about which options are a go and which ones are a no. Use this time to encourage and re-encourage your friend. Confidence is key.
Now, as you reconvene you come to step four. This is the big move for you as the wingman and your friend. Let your friend and the target pick up where the other conversation ended. A sassy way to get your friend to talk to his or her target is to ice them out of the conversation so they have no one else to talk to but each other. Turn your back to them and just keep talking to the rest of the crew.
From there your job as a wingman is complete. Trust the confidence you instilled and his or her natural skills of flirtation to wrap up the job. Step five is only to be an open ear to hear about the success of your friend’s endeavors, or a shoulder to cry on should things not go as well as planned.
At the end of the night the wingman might not be taking any one home, but the wingman gets the satisfaction and confidence from a job well done.
