Can two serial cheaters get a second chance at love? After a one-night stand in college, New Yorkers Lainey and Jake meet by chance twelve years later and discover they each have the same problem: because of their monogamy-challenged ways, neither can maintain a relationship. Determined to stay friends despite their mutual attraction, they make a pact to keep it platonic, a deal that proves easier said than done.

Lucy, a self-styled teenage rebel, wants to leave the painful, boring world of her high school and suburb behind. She decides to run away with Sheila, her photography teacher, with whom she has a secret relationship - without realizing that Sheila might not share her vision of this perfect escape.