Written by Emily Nagoski, Ph.D.
Well. The short answer is "You ask them out. Just fuckin' do it." Which is not helpful, but actually is true.
Let's see if we can't dig a little deeper.
What's the risk in asking someone out, initiating the first kiss, being the first to say, "I love you"?
Why, the risk is that the other person will respond with revulsion, pity, horror, derisive laughter or some other variety of REJECTION. They'll say NO, they'll turn you down like a bedspread, because let's face it you're a loser anyway and why would someone as great as them want to be with a loser? (Says the voice in your head.)
I could at this point write a lot of stuff about how being turned down by a crush object doesn't say anything about your value as a person and that you shouldn't take it personally, and that would all be absolutely correct, but dude, it fucking SUCKS to be rejected by someone you like. The more you like them, the more it sucks.
Everyone wants the other person to be the initiator, not only because we want to avoid the risk of rejection, but also because we want to feel pursued, wanted, desired. We want to feel that we were worth the other person taking that risk.
Well SOMEONE has to be the first, and you're the one clever and curious enough to read this blog post, so I say you're the one who should make that move.
What you need is some way to tell whether or not the other person is likely to be receptive, a way to tell whether or not they like you. Though you can't know for sure how a person will respond to any initiation, there are ways of telling whether or not you're connecting strongly with someone. Body language is the simplest:
Now, just because you're connecting strongly doesn't necessarily mean they're attracted to you. But it's a good start.
Also, it's perfectly possible that your hormone-addled brain won't be reliably capable of interpreting your crush object's behavior. If you find yourself uncertain and unable to think clearly about it, call on the more rational perspective of your friends. Let them watch you and the crush object interact, and ask them to tell you honestly if they think there's anything happening on the other end. Be sure they can be objective too; they mustn't look for evidence that the crush object reciprocates, they must look for evidence either way.
So say you're connecting well and your friends think the person might be into you. Now's the time to ask them out. You can ask them to do something that's ambiguous in its intent (not a date, but going together to an event that appeals to both of you, or joining your friends for a drink, or whatever). "I think you'd have a good time," is a safer, more ambiguous sentiment than "I think I'd have a better time if I went with you than if I went without you." Save that for the second date.