As a flirting and dating coach, I often am asked, “What do I do if I am super shy? It takes me a while to open up.” My answer? Grab a wingman (or wingwoman)! These super heros masked as your friend can make all the difference when it comes to meeting people and starting the ever important first conversation. However, there are a couple rules that come into play when picking a wingman, and not all friends are created equal. Here are my five rules to make sure the person you bring along will help you to get your flirt on to the max: 1. They must be trustworthy. No, you aren’t marrying them, but you need to be able to trust them to stay with you during the night, and stay on track. A friend that is going to wander off and ditch you when they find someone they are interested in, isn’t a good wingman. They need to be committed to you – just for the night. Knowing when to sweep in, and knowing when to back off. 2. They must be single. I know, I know. Your married best friend insists that he/she is the best choice for your winged companion, and I am sure they are awesome. However, if you have an option, you must pick a single, fun and flirty friend. Your attached friends love you and want to see you happy, but they may not have the patience to let you work your magic. The last thing you want is pointed, probing looks from your wingman indicating that you should wrap it up so he can continue complaining to you about his wife… or so he can get home to her early. 3. They must be fun. Fun is hot! It is so attractive to see happy people having fun. Pick a friend who is fun and goes with the flow. Have a funny friend? Even better. Laughter is contagious and can draw people in to talk to you like flies to honey. Who doesn’t like to laugh? 4. They must be selfless. They needs to be completely focused and committed to the cause - you! At least for the night. Your wingman needs to recognize that their role is to help you. You get first choice, and she needs to play a supporting role. Her job is to keep an eye out for you, keep an eye on you, and keep herself in check. Impaired or wasted wingwomen tend not to be effective. That doesn’t mean she can’t have fun and meet people too—she just needs to put you first (it’s only a few hours, they can make it). 5. They must know you. That seems a little vauge, huh? What I mean by “know you”, is that you need to make sure your wingman knows you well enough to know your type and read your cues. That way they know who to be on the lookout for, when to back off, or when to come in and save you! A good wingman won’t leave you hanging when you are looking distressed by the conversation. Still at a loss for someone to have your back? Hire a pro. No, really. One of my friends, Thomas Edwards, is literally a Professional Wingman. Give him a shout. Tell him I sent you, and be sure to let me know how it goes!