Math teacher Olive Kitteridge attempts to help Kevin, a smart but timid student whose mother is suffering from depression. Her son Christopher isn't happy though. Henry goes on a hunting trip that concludes with a tragedy.

Kevin returns to Maine and Olive is able to convince him to stay over and attend Christopher's wedding-rehearsal dinner. Olive clashes with the bride's mother and scares the flower girl at the ceremony.

Olive visits Christopher and his second wife in New York, but abruptly returns to Maine, where she gets some bad news about Henry, and ultimately befriends a lonely widower she meets while out for a walk.