PlanJam!From your screen to the scene

Some women only go after that strutting, slick-haired man, oozing over with confidence and masculinity. Fortunately for the many women who fawn over him, this kind of man makes the whole "I'm interested" thing easy. Want to get him to talk to you? All it takes is a glance and a smile.

But some of us, myself included, have a strange attraction to that sexy, shy guy who sits in the corner and has trouble making eye contact. There's a sense of possibility about him, of something sweet and undiscovered. Especially (you have to admit it) when he's good looking. Unfortunately, though, part of what makes him so attractive to you – that quiet sort of mystery – is also what makes it hard to get anywhere with him. Because a shy guy is just that – shy – and getting him to ask you out can be like pulling teeth.

So how do you get a shy guy to ask you out?

The best answer is…you don't. Because if you have the confidence to do most of the work yourself (or can fake the confidence with a pair of mile-high heels and some sexy perfume), you don't have to wait around for Mr. Sexy-Downcast-Gaze to ask you out. In fact, you'll be doing him a huge favor if you approach him. To a shy guy, having a woman approach him instead of the other way around can be like that last-minute call from the judge offering a death row reprieve. For some, shyness really is that debilitating.

See him often? Start off by striking up a conversation one day, being sure to keep the conversation friendly and flirty – making him laugh is a great way to get him to relax. Next time you see him, ask him if he wants to get a cocktail or a cup of coffee. Keep it casual. There's no need to be too forward or ask him on a romantic date the first time you talk. In fact, if you do that, he might be so overwhelmed that he won't know what to say.

But no matter how your do it, if he's been pining over you for months with nary a sign, he will be falling-over-his-feet grateful that you decided to make the first move.

"Ask him out?? I can't!"

It's true that like attracts like, and you may be too shy yourself to approach your shy guy and tell him that you're interested. In this case, you'll need to give him some un-miss-able clues that you're into him. Which means, of course, that you've got to swallow your shyness (a glass of wine first may help with this) and…flirt! Look at him, smile, then look away. Hold his gaze for a moment, lick your lips, toss your hair, and do all of the girlie stuff that men find irresistible. Touch him, get close to him, and make sure that a blind and deaf person would be able to tell that you're interested.

If he still doesn't bite, he's either so painfully shy that you're going to be forced to do it yourself…or he's not interested. Take a deep breath, put on a smile, and let him know how you feel. It may just help him get over his shyness…and you over yours.