Lynn feels like it's time to start dating again and decides to start by asking out her next door neighbor, Joe. Sophie, against her mother's wishes, decides to go to a party and gets caught in the act. Elsewhere, Karen gets stood up for a date with a modeling agent, whom she thought might further her languishing career. Sophie learns about the bet.

Lynn, Sophie, and Karen are invited over to the Fiskes' home in Hamptons for a weekend. Sophie, Lynn, Karen, Joe, Gideon, Annabelle, Paisley, and Evan all end up going. Sophie decides that she will forget about the bet and her and Nicky can just be friends. Annabel comes hoping to get a chance to tell Gideon how she feels. While there, a game of "Truth or Dare" gets a little out of hand. Also Rona's and Julian's marital problems surface.

Lynn is asked by Toby to submit a design for her company's fashion launch and asks Karen to model for her; Julian and Rona discuss their marriage; Sophie and Annabelle compete for a photography internship that is being judged by Gideon's father.

Karen escapes from her stalker, but returns home and is confronted about her drug use. Sophie must choose between Gideon and Nicky’s invitation to a school formal. Finally Lynn's ex-husband comes to New York and demands that Karen and Sophie move back to New Mexico.