It's Friday night and you're poised at Luxbar, decked out in a glittery cami and pencil skirt and some fierce heels (never mind how you're going to walk home, now that CTA has reduced buses and overnight routes.) That twinkle in his eye and Absolut cocktail in his hand have you captivated; he exudes class but a certain bad-boy spirit that draws you in. No rings, and his wingman just headed for the bathroom.. The stage is set.
How do you make your move?
Approach him confidently. Have a goal in mind, and keep your eyes on the target. You have only 20 seconds to make a lasting first impression. Instead of going right in the for the prize, be aloof - wave a bill at the bartender to flag for a drink.
Have something to say. Pickup lines are meant as conversation starters, but the best way to reach him is probably going to be with a more personal line. Ask about the score on the game, or what he thought of that last play. Consider picking up a few pointers from a wine and spirits magazine - correctly naming his rum and coke a "Cuba Libre" will impress him with your trivia knowledge.
Head for the end zone: His number. Take your cue from the conversation on this one. Is he into sports? Invite him to a game. Is he talking about a jobsearch? Offer to go over resumes together or hit the highlights and lowlights of the interview process. Reassure him that this is a casual date - no fuss (even though your intentions are much more than that, keeping it relaxed is best for a first encounter and tells him that you are a free, independent person.)
Most importantly, be yourself. Be honest about what you are after. While you don't have to share everything, i.e. salary or how long you've been on the market, the more candid you are, the more comfortable he will be talking to you.