Prance Charming

I'm an accomplished, caring, sensitive, and funny guy. I do well talking to women in social situations where I've had time to warm up. I'm not great at approaching women on the street. How can I increase my street-side "swagger"?

--Need Game

The stride itself -- that wide-legged rolling gait -- isn't hard to adopt. Just pop a sleeping gerbil in your underwear. But you're probably talking about the street meaning of swagger: self-assured cool. That's a way of being that you can't just throw on like a sweatshirt. Guys who try to put it on usually end up coming off cartoonishly cocky. Sometimes what's most endearing about people are the small ways they aren't totally put together, especially if they're gutsy enough to put themselves out there, flaws and all. So maybe talk to compelling women you see on the street -- a tough audience for any guy -- but do it as you, not with your best imitation of Jay-Z. And accept that your natural hunting ground is probably your local coffeehouse, where you won't have to charm a woman before the light changes and she won't immediately suspect that what you're really saying is, "Hi, I'm a purse snatcher, and I was wondering if I could distract you with some small talk while I root around for your wallet."