12. Liberal Arts (2012)
The pairing: Jesse (35) and Zibby (19)
The age difference here isn’t too extreme, and Zibby is of legal age. That having been said, it’s always unsetting when a professor sleeps with a student at his college, even if she’s the one doing the seducing.
CORRECTION: They never actually sleep together, and he’s not a professor at her college. So the romance in Liberal Arts isn’t really creepy at all — though some would consider the age gap to be inappropriate.