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Celeste (Rashida Jones) and Jesse (Andy Samberg) are high school sweethearts who married young and are now at a crossroads at the age of thirty. While Celeste is a success in business, Jesse is unemployed and adrift. Celeste thinks that if they divorce now they could still remain friends. Jesse passively accepts the decision even though he is still in love with her. As reality sets in, Celeste slowly and painfully realizes she has been cavalier about their relationship, but her timing with Jesse is less than fortuitous.