Celeste and Jesse have been best friends forever. They dated in high school, got married, and now they're getting divorced. Their best friends don't think they can maintain their friendship throughout the dissolution of their marriage, but Celeste and Jesse don't think there will be a problem. But that's before Jesse gets into a relationship that Celeste doesn't think he can handle, and Celeste finds it harder to move on than she originally thought.

As he eases into adulthood at the age of forty, Conrad Valmont (Jason Bateman), the over-educated, under-employed heir to the Valmont Hotel fortune, is cut off from his allowance following his parents abrupt divorce and tossed out into the unforgiving streets of the Upper West Side. Luckily, he is taken in by his old friend Dylan (Billy Crudup), and returns the favor by immediately falling for Dylan's girlfriend Beatrice (Olivia Wilde). As Conrad attempts to woo Beatrice while keeping both their relationship and his bank balance secret, Dylan tries to set him up with Jocelyn (Jenny Slate). Ever committed to the charade that he eventually finds difficult to maintain, Conrad quickly realizes his charm can only extend so far into debt. Now deep into an extensional reflection, will it take losing everything to make Conrad realize what he can truly become?

Sam, a divorced ad exec, loses his son in a university shooting. At the wake at his ex wife's house, he meets his son's SO, Kate. Two years later, after many bottles of booze, he lives on his yacht and works as a house painter. He meets up with his two workmates after work at a bar. He keeps his past a secret. When his ex finally tracks him down to get his signature to sell their house, she leaves him their son's music things including recordings of his own songs. Sam brings his guitar to the open mic night at the bar and sings his son's song. He gets his first fan, Quentin, who sees potential. Quentin manages to convince Sam to start a band/quartet (Rudderless) playing "Sam's" songs.

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