1. At a bar.
Brave: Buy them a drink. You can do this by going up to them and saying, "Can I buy you a drink?" or you can do that thing on TV where you tell the server you're paying for their next one. Then they'll look over, and your eyes will meet across the room, and then [seamless transition into sex scene].
Brave-ish: The next time you need to get up to go to the bathroom, do that thing where you needlessly brush them as you walk past, like, "OMG it's so crowded in here, sorry I have to squeeze by you!"
Awkward: Drink a lot and stare.
2. With your barista/server.
Brave: Leave your number on the receipt. It is literally the lowest-risk flirting move. Just make peace with either pretending it never happened or finding a new coffee spot if it doesn't go as planned.
Brave-ish: Slowly incorporate non-order conversation into your interactions, even if it's something as simple as complimenting that leaf they just "drew" on your latte. ("What you do is art. No, it is.")
Awkward: Visit the coffee shop so often that you no longer even enjoy it. When you order, consider saying something playful, but then just order so quietly that your crush has to ask you to repeat yourself at least twice.
3. At work.
Brave: Utilize the happy hour to your best ability, whether it means your suggesting one in the first place, or transitioning from one into after-hours activities. The "how" of this is murky. But the happy hour is the key.
Brave-ish: Pay very close attention to when this person arrives at work and leaves work. Maybe you would also like to start getting to work and leaving work around these times? And see them in the elevator a whole lot? Just coincidentally.
Awkward: Type this person's name into the "To:" field of a work email or Gchat box and close out of it immediately a few times. Thrilling!!
4. At a party.
Brave: Make eyes at them for 20 minutes, then introduce yourself, then talk for a while, and then say, "Do you want to get out of here?" (Unless it is their party, because that would be confusing. In that case, just linger endlessly.)
Brave-ish: Drink semi-heavily. If people are dancing, situate yourself among them, in an area with high visibility. Then dance really inappropriately. If people are not dancing, do this anyway.
Awkward: Leave. Go home. Later, text a friend who is still at the party and ask, "What is [crush's name] doing now?"
5. In school.
Brave: You basically have a built-in date, and that is the study session. Extend an invitation their way and then pretend to be very surprised when no one else shows up.
Brave-ish: Strategically place yourself in their vicinity and mumble a hilarious quip or brilliant insight "under your breath." Your wit and charm is irresistible.
Awkward: Spend half a semester figuring out their name through process of elimination in class-wide emails. When you're confident that you've settled on the correct name, write it down over and over in your notes. Looks good!
6. With a friend of a friend.
Brave: Tell your mutual friend that you think this person is cute and seems pretty funny. Ask if she could set you guys up, or at the very least, help you coordinate a group hangout during which you would meet.
Brave-ish: Stalk your mutual friend's Facebook wall for interactions with your crush and use this as entrée into a casual but investigative conversation about the possibilities of your future together. Ex.: "Hahaha who is that person who left that Game of Thrones supercut on your wall, have we met, also are they single hahahahaha."
Awkward: Drop their name into conversation with your mutual friend, apropos of nothing. Repeat until your friend outright asks if you are interested in this third party, but then be indignant in your dismissal of the question.
7. With a friend.
Brave: Tell them directly that you'd like to move from friends to more than friends, because you're mature, responsible adults who respect each other.
Brave-ish: Subtly steer them toward a conversation about sex and/or relationships, and test the "wouldn't it be crazy if we dated hahahaha?" waters. Maybe drink a little? Never underestimate the power of the accidental arm graze.
Awkward: Continue to do the innocuous, thoughtful things that friends do for each other, but decide that these are now romantic gestures, imbued with your deep desire. Do nothing to suggest this shift to the other party.
8. On Facebook/Twitter/social media at large.
Brave: Social media might be a great(-ish) way to meet cute strangers, but to get this thing offline, you have to take your flirting private. Send a Facebook message or a DM. What should it say? Who knows. I dropped you off, you're on your own now.
Brave-ish: Like their statuses and/or fave their tweets just a liiiiittle bit more than you would for anyone whom you also like but don't want to sleep with. Maybe they will notice this?
Awkward: Late one night when you've been drinking and are wearing pajamas, open their Facebook profile and click every picture they have ever been tagged in. Accidentally click "like" on one from 2009. Never speak to this person again.
9. With a total stranger in a public place.
Brave: Give them your number. There is nothing to lose. You will literally never see this person again. (Unless it works, in which case, hooray!)
Brave-ish: Make suggestive eye contact and give a non-creepy smile. Stand close enough that conversation would be possible and even convenient, and say something that sounds like it's purely functional, such as: "Do you know if the F train is even running?"
Awkward: Decide that you've shared a real moment and then leave the environment immediately. Formulate the perfect "Missed Connection" on your way home, but then just scroll through Tumblr for a few hours instead.