We know you always hang out at home, you lust books and those big round spectacles enhance your style. You are attracted towards girls, after all you are a boy. Social gatherings and public places freak you out. Approaching a girl at a social place gives you hebbie-jeebies.
It's better if we do not talk about the kind of flirting that is already a nightmare for you. But then again, you are a nerd who needs to get out there and have some fun with girls.
Brave: Use your happy hour to the best of your ability. Brave-ish: Pay close attention to when she arrives at the office and when she leaves. You too set your timings like her, maybe you can catch her in the elevator. Awkward: Bring her a cup of latte, "now we don't need to go for a coffee."
Brave: The lowest risk move, leave your number on the receipt. Brave-ish: Just incorporate non-order conversation into your interactions ("What you do is art. Yes, it is"). Awkward: Walk often into the coffee shop, then at one instance pretend that you don't like it anymore and being playful, place the order so quietly that your crush has to ask you to repeat at least twice.
Brave: Give her your number, there is nothing to lose, you will literally never meet this person again. Brave-ish: Make a suggestive eye contact with a non-creepy smile. Stand close enough to start a conversation, then say "How you doin'?" or "The whether seems good". Awkward: Decide that you have shared a real moment and then leave the environment immediately. Formulate the perfect "Missed Connection" on your way home.
Brave: Social media is a good way to meet cute strangers. Just leave a direct message. Now you are on your own. Brave-ish: Like their posts and Fave their tweets just little more. Maybe, you will get noticed. Awkward: Wake up one night wearing your pajamas, like a pic of random girls. Next morning you may delete your account.
Brave: The built-in date, extend an invitation for a study session. Brave-ish: Ask her if you two can study together. Awkward: Spend half a semester, figuring out her name by eliminating class-wide emails. When you find it write it down over and over in your notes.
Brave: Tell her that whether she would like to be more than just friends. Brave-ish: Steer the conversation towards sex or relationship and test the "wouldn't it be crazy if we dated hahahaha?" Awkward: Do thoughtful things that friends do for each other with the intention but decide that these are romantic gestures.
Brave: Make eyes at her for some minutes and then introduce yourself, talk for a while and then say, "Do you want to get out of here?". Brave-ish: Drink semi-heavily, dance inappropriately, in a high visibility area you will get noticed. Awkward: Go home, text a friend at the party and tell him to ask the girl's friend.
Brave: Buy them a drink. Start with 'Can I buy you a drink?', or you can do that thing from the TV, where you tell the server that you are paying for the girl. They will look over, and your eyes will meet across the room. Braver: She is standing near the restroom, get up and brush her as you walk past her. OMG, it's so crowded in here, sorry I have to squeeze by you!" Awkward: Drink a lot and stare.