The gals over at Lemondrop featured a great move for a shy girl to initiate a conversation with a guy at a bar. It's such a great technique that I've unwittingly been the victim of it without even knowing (be sure to check it out).
There are some guys who do the not talking thing pretty well, they're called Silent Assassins and they're usually very handsome, rich or somehow renowned (or some combo thereof). But other shy guys have employ a few great little moves to get the ball rolling, sometimes these moves are a little too subtle, so for your edification here are a few shy guy* techniques so you know when he's hitting on you (from most to least obvious):
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5) "The bartender gave us too many drinks." You'd be surprised how often this works. For the most part, everyone is in on the scam (especially with shots or champagne) but it provides the same opportunity to "open up a set" as buying drinks but without all the pressure.
4) "Damn it all to hell, my buddy is talking to some girl, do you play pool?" His buddy may not exist. The cooperative competitiveness of doubles billiards may open a lot of doors. Plus all of that talk of sticks, balls and pockets should lead to some really fun double entendre repartee. (My one actual piece of advice to ladies on the prowl is to become competent at pool and/ or Buck Hunter, trust me on this one.)
3) "I'm trying to find "Whatever You Like," do you know who sings it?" The jukebox is a fantastic resource for the shy guy. He may carry extra singles in case you're riding with just your credit card and ID. He may run out of songs he wants to hear on his fiver and start taking requests. You may end up dancing and singing along with him to TI.
2) "Does this look stupid?" Critiquing fashion is second-nature for most gals. And it's almost a cliché that a guy needs some sort of sartorial support. Whether or not to peacock that sweet belt buckle is an old fallback (AKA to front tuck or not to front tuck**).
1) "After you order your drinks, can you please send the bartender to me?" Objective one: he's implied that you're attractive. Objective two: he's identified that he is a gentleman by letting you go first. Objective three: he's shown a modicum of vulnerability by admitting that he needs help. Objective four: the ice has been, if not broken, chipped. The flip side of this move is that he offers to get the bartender's attention and proves that he's chivalrous and connected (yeah yeah, it was in Knocked Up, big whoop, wanna fight about it?).
Stay alert and you may just bag yourself a shy guy.
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*Note: Unlike hot girls, shy guys don't meet in groups, we tried once and no one would talk first.
**Note: In some precincts, it is called the "frat tuck."