I Tried It: Making the First Move

I've always considered myself a go-getter. When I see something I want, I charge ahead (sometimes recklessly) and do whatever it takes to get it. Which makes it all the more surprising that, at 28 years old, I had never made the first move on a guy. Call it shyness or a fear of rejection, but I'd never been the first to say hello, send over a drink during happy hour or ask a man for his number. And I was long overdue the experience.

So with the help of a wingman (known for her ballsy approach to flirting) and a first-move coach (known for his no-fail pickup maneuvers), I prepared myself to dive into the New York City social scene to face my fears and maybe actually meet a nice guy or two.

The Rules

The First Rule of picking up a man: Recognize that, as a woman, you automatically have the upper hand. I like to call my upper hand "breasts." And nice-smelling hair. So if you want to strike up a conversation with a man you've never met, and you look and smell better than his college fraternity brothers, he's going to think he hit the jackpot.

The Second Rule of picking up a man: Have something to say. It sounds obvious, but nothing will take the wind out of your First Rule sails like finally summoning the courage to approach your Tall, Dark and Handsome and then stammering out a line like, "Uh, so, do you like stuff?" If you can't think of something to say, try asking His Handsomeness for his opinion. Tell him you have a bet going between you and your friends that you need him to settle or an argument you need him to weigh in on. Men love to give their opinions, so you'll be chatting it up in no time.

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