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

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

Olive goes to see Christopher and his second wife in New York, but soon returns to Maine, where she receives bad news about Henry.