The Good Girl (2002)

Justine's (Jennifer Aniston) adult life is not what she had hoped it would be.  She works at the discount store in the small town she grew up in, she's married to Phil (John C. Reilly), the guy she settled for who paints houses for a living and gets drunk with his buddy Bubba (Tim Blake Nelson) on her couch after work every night.  When she begins to eat lunch with her co-worker at the "Retail Rodeo", Holden Worther (Jake Gyllenhaal), she finds a kindred spirit who is just as miserable as her.  In fact, Holden is convinced that he's the real life version of Holden Caulfield, destined for great things.  What starts as a friendship over lunch breaks turns into a hot and steamy affair with a younger man with implications that could tear her life apart and break her husband's heart, but that's not her!  She's always been The Good Girl! The always sexy Jake Gyllenhaal has a quick jack-off session in one scene as well as a motel tryst with Jen, but it's the surprise full frontal from Tim Blake Nelson that provides the real deal Man meat in this cult classic indie flick!