The film follows two friends, Rick and Fred, who are granted a week off from marriage by their wives, so that they can sleep with any woman they want after their wives notice they are obsessed with sex.
- Abhorrent Admirer: Brent to Leigh.
- All Men Are Perverts: The premise of the movie; two guys are obsessed with sex, and realizing this, their wives decide to give them the titular "Hall Pass": A week off from marriage during which they can have sex with other women.
- Ambiguously Gay: Gary. While he's married, this comes especially in the ending, when his wife suggests they do the hall pass, and he has an Imagine Spot in which doing so causes a chain of events that ends with him getting thrown into jail and getting anally raped. He still decides they should try it out.
- Casanova Wannabe: Rick and Fred have a really hard time picking up girls. Rick in fact only has sucess with Leigh, a woman he had met some time beforehand.
- Cool Old Guy: Coakley (Richard Jenkins), the Badass Grandpa who mentors Rick and Fred on the art of picking-up women.
- Cringe Comedy: The guys' activities during the "week off" given by the hall pass. When they decide to play golf, they get too high from eating hash brownies and wreak havoc on the golf course. When they decide to get drunk in order to become more loose to pick up women, they end up getting too far and into a fight with other customers. And then there's Rick and Fred's whole ordeal when they though that they were finally gettin' some.
- Divorce Is Temporary: The film's main premise, albeit deliberately invoked.
- Fan Disservice:
- Two naked men come out to pull Rick from the hot tub after he loses feeling in his muscles. We get a greeeeat close-up of a guy with exceptionally small manhood.
- There's also the girl whom Fred picks up; she sneezes out something extra...
- Imagine Spot:
- Rick imagines what would happen if he brough alcohol to/hooked up with his kids' babysitter, which is a week from turning 21. He imagines getting arrested, being fired from his job, divorced, and unwanted at his kids' weddings.
- Gary imagines how life for him would be if he got a hall pass. It doesn't end well ...or does it.
- Male Gaze: Rick and Fred do this so obviously that their wives notice them even when they act like they're not.
- Ms. Fanservice: Leigh, and maybe Paige as well (Paige is played by Alexandra Daddario, after all).
- Refuge in Audacity: This is a Farrelly Brothers film, so obviously...
- The Sociopath: Brent. His response to someone hooking up with the girl he was interested, even though himself never actually asked her out? Vandalize his car. His response to someone having sex with his mother (or thinking he had)? Shoot the guy dead.
- The Stinger: Gary's wife sees how happy they are and suggests they do the hall pass. He imagines sleeping with an Asian woman whose husband finds out, and then ends up killing him, the woman, her grandmother, and a couple of teen witnesses, ending with him getting arrested, thrown into jail and getting raped. He still decides they should try it out.