7. Show both insecurity and slight craziness.

Learned from: Swingers (1996)
Complex says: Some people think that simply adding a phone number into your Blackberry’s address book qualifies as a successful pick-up attempt, but not us. For one, the female bar-crawler could’ve given one of those infuriating wrong numbers. Assuming you’ve been spared such humiliation, though, the next step, calling her, is even more important. Just because you’ve scored a girl’s digits, that doesn’t mean the deal’s been sealed. To keep yourself in the game, don’t ramble on like a timid 13-year-old while leaving her a voicemail, like Jon Favreau does in this painfully awkward scene from Swingers. Not only will the cold-hearted dame never call back, she’ll probably save the voicemail and play it for all of her lady-friends. Meaning, you’ll have to move to a different area code.