For most of their Hall Pass week, Rick (Owen Wilson) and Fred (Jason Sudeikis) fail miserably in their attempts to pick up women. Meanwhile, their wives Maggie (Jenna Fischer) and Grace (Christina Applegate) are in Cape Cod, having a blast hanging out with a minor league baseball team. The team's manager seems to have a crush on Maggie while a player named Gerry flirts with Grace.
On the last night of the Hall Pass Week, both husbands and their wives have chances to cheat. At a party, Rick finally gets propositioned by Leigh (Nicky Whelan), a pretty Australian barista at his favorite coffee shop. But he decides he loves his family too much, and can't go through with it.
In Cape Cod, Grace has sex with ballplayer Gerry, and is crushed to find out he never really cared about her. She starts to drive home in tears. Meanwhile, Maggie is having dinner with the ballclub's flirtatious manager.
Rick and Maggie's babysitter Paige has a horny aunt who goes to Rick and Fred''s hotel room, hoping to seduce Rick. Fred answers the door, and pretends to be Rick. He tries to have sex with Paige's aunt, but can't keep up with her, and fakes performing oral sex on her.
Brent, the obnoxious barista who works with Leigh, turns out to be the son of Paige's aunt. Brent is furious at Rick, who he thinks has had sex with his mother, and vandalizes RIck's minivan. Fred gets a phone call that Maggie has been in a car crash and is in the hospital. Fred and Rick drive the trashed minivan together to Massachusetts, to see Grace. The crazed Brent, however, climbs on the roof of the van and stays with them the whole way. When they reach the hospital, the maniacal Brent attacks Rick and Fred, and is arrested. Fred finds out that Christina is all right, and he apologizes to her for ever wanting to cheat.
Rick finds Maggie, makes his own apology, and learns that nothing happened between Maggie and the manager. Both couples are reconciled and seem to be much happier as a result.
Post-credits scene: at a backyard barbecue, Gary's wife sees how happy the couples are after their Hall Pass week, and asks if Gary would like a Hall Pass. Gary has a lengthy vision of what might happen: he sees himself sleeping with an Asian woman, then being forced to murder her husband. Later, Gary must murder the woman, her mother, and four eyewitnesses. He envisions himself being imprisoned and sodomized by a big convict. But even after envisioning all that, he says a Hall Pass would be a great idea!
Thanks John L!