Anna Breslaw, Glamour magazine
Did you know eyef*cking someone at a coffee shop for more than five seconds can lead to serious retinal damage? OK, that's a lie, but bite the bullet and ask him out already.
There's a guy who always stares at me in a coffee shop, and I stare back and giggle like a demented person, and then I leave, and we wave goodbye and I giggle some more, and the whole thing is sort of cute and sickening and gross, and he has no wedding ring.
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"Ask him out," said my friend Ben.
"But what if he's just a creep who does that to everyone?"
"Ask him out," said Ben.
"But what if he's turned off because I'm the one who's being proactive?"
"I hate you. Can we talk about something else?" said Ben.
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So you heard it here! Boys make passes at girls who, uh, make passes. But here are some ways to do it without coming off like an idiot (at least, as far as I've discerned them).
Be brave! Don't just hand him a number and run away. Being brave is especially easy when he has a dog or is wearing some sort of interesting piece of clothing, because then you have something to talk about.
If you guys keep running into each other because you live in the same 'hood, suggest a place for the date that neither of you have tried. New experiences! Together! (Or check out our cheap date ideas, derp.)
Wait a few silent-flirt times before you make your move. Like a cheetah in pursuit of an antelope, be stealthy and patient.
Don't overstay your welcome. That'd be overkill: get in and get out. Get a yes and then pimp off into the horizon immediately. (See: importance of body language!) You can chat on the date.
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Things you can wear: Jeans. Shorts. A casual skirt or dress.
Things you can't wear:A muu-muu. A semi-formal dress. Your old debutante ball gown. A wedding dress. Your mom's wedding dress. A Victorian ghost's wedding dress.
Act confident, not weird and ashamed or overly self-deprecating. I have found that the trick to this is pretending you love yourself. Actually loving yourself would probably work also but I'm not quite there yet.
After you actually do the asking, for the love of Pete, be passive. No texting, no emailing, no following up of any kind. You put your legwork in. Now it's his turn.