How to Crack The Shy Guy

Ah, the Shy Guy: that rare specimen of man who you’ll never overhear  talking bragging about some meaningless hook-up. You won’t find him at parties or see him hamming it up for the ladies. He’s sweet, modest and avoids being the center of attention at ALL costs. Odds are, he’ll be the one sitting in the back of class, avoiding eye contact with the professor when he or she scans the room for a volunteer.

He’s pretty much adorable, really. Mysterious, intriguing, sensitive, endearing … a diamond in the rough (“the rough” being the obnoxious, masochistic guys that are just way too common in college). Shy guys are hot. Think Michael Cera. Mmmm.

No? Just me?

Anyhoodle. You’ve caught him glancing furtively in your direction on many (many) occasions. You’re interested. He’s interested. But the two of you both know there aren’t gonna be any suave, hey-baby-what’s-your-sign moves on his part. So, short of holding up a “Hey. You’re cute. I’d say yes if you asked me out” sign, how d’ya go about meeting/cracking open the shy guy?

Approach him casually and strike up a small convo. While he prrrobably won’t be bowling you over with witty banter and charm, he won’t run away. Do most of the talking, but toss in lots of open-ended questions. Just keep it light and impersonal at first: topics like homework, professors, something on the news. Do this a few times a week to establish a bond and tear down that wall he’s got up.

Spend time as friends, without pressuring him about dating. Hang out with him alone, rather than with your other friends. Be patient. It takes the shy guy some time to become relaxed and show his true self.

Be approachably attractive. The root of shyness is insecurity, so it’s more than likely that he thinks you’re out of his league. So now isn’t the time to try out cutting edge fashion or over-the-top makeup. Try for “cute” rather than intimidatingly gorgeous (that’s a toughie, I know).

Arrange a few quiet dates if he doesn’t get up the nerve to ask you out. Keep it casual, and— again — keep it one-on-one. Clearly, the shy-guy isn’t going to do well in a large group of your girlfriends shrieking about vibrators. Choose something low key and easy like a movie, where there’s less pressure to talk.

Gauge his feelings for you. Talk about what you’re both looking for in a person, and drop hints that what you’re looking for is him.

Help him feel confident around you. Every male has an ego — find ways to boost it sincerely. Subtly compliment him. Let him help you with something, whether it’s a homework problem, fixing your computer, or finding the latest gadget. Or — and this is probably the best confidence booster–  see him when he’s in his element. He’ll be MUCH more open and charismatic when he’s somewhere he feels totally comfortable.

Once you enter the relationship zone: First of all, yay. Second of all, introduce him to your friends and family slooowly, starting with the quiet, less intimidating ones. Yeah, save loud Uncle Frank and Over-The-Top Tina for when he’s more comfortable in the relationship.

The shy guy is SO worth the effort and patience. Think of him as … a gift. A treasure to unwrap. A rare and special treat that not everyone gets to see. If you can stick out a few awkward silences in the beginning, I guarantee you’ll have landed yourself a respectful, fun and totally caring guy.

[Photo courtesy of MariaTarescaCB on Flickr.]

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