An uptight documentary filmmaker and his wife find their lives loosened up a bit after befriending a free-spirited younger couple.

Based on the true childhood experiences of Noah Baumbach and his brother, The Squid and the Whale tells the touching story of two young boys dealing with their parents' divorce in Brooklyn in the 1980s.

After his first date at age 15 ended with the girl making out with another man at a party, aspiring writer Lester Grimm has treated all his girlfriends with jealousy and suspicion. While dating Ramona Ray, paranoia gets the best of him when he discovers that her most recent ex is successful novelist Dashiell Frank. Lester begins attending the same group therapy sessions as Dashiell to learn about Ramona's past with him.

After college graduation, Grover's girlfriend Jane tells him she's moving to Prague to study writing. Grover declines to accompany her, deciding instead to move in with several friends, all of whom can't quite work up the inertia to escape their university's pull. Nobody wants to make any big decisions that would radically alter his life, yet none of them wants to end up like Chet, the professional student who tends bar and is in his tenth year of university studies.