Requested by @samboyd
  1. Pretty in Pink
    Your best friend won't stop sexually harassing you, and you have a crush on a rich douche bag.
  2. 27 Dresses
    The most important thing about your personality is that ever since childhood, all you've dreamed about is your wedding.
  3. Sweet November
    I haven't seen this one (is it even a rom-com), but I think at least one of them dies?
  4. You've Got Mail
    The tragic irony is that BOTH your businesses are ultimately doomed.
  5. My Best Friend's Wedding
    You lose.
  6. Pretty Woman
    You are a prostitute.
  7. 50 First Dates
    You are brain damaged and someone is exploiting this fact to fuck you.
  8. Serendipity
    This is the one you are most likely in.