Lynn, Sophie and Karen decide to throw a dinner party. Sophie invites her photography teacher, hoping to set him up with her mother. Meanwhile, Lynn lands a job at a fashion company and Karen gets a job she's not too fond of -- a nightclub waitress.
After deciding that it's time to start dating again, Lynn tries to get back into the dating scene by asking out her next-door neighbor, Joe. Meanwhile, Sophie, despite her mother telling her not to, sneaks out to a party, but gets caught in the process. Elsewhere, Karen gets stood up on her date with a modeling agent and Sophie learns about the bet.
Lynn is given the opportunity to fly to Chicago to run a fashion show. She decides to take the offer and leaves Sophie and Karen home alone. In Chicago, Lynn runs into Julian, who tries to convince Lynn to give their past romance another chance. Back in New York City, Sophie and Karen get lost in Central Park.
Lynn, Sophie, and Karen are invited over to the Fiskes' home in Hamptons for a weekend. While there, a game of "Truth or Dare" gets a little out of hand.
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.
Ex-husband Daniel plans to fight for custody of Sophie. Elsewhere, Karen takes undesirable assignments to move up in the modeling world, Lynn and Julian's relationship takes a toll on their kids, and Gideon sees Annabelle in a new light.
On Parents' Night, Sophie causes an uproar by snubbing her mother to invite Daniel, who proceeds to clash with Julian. Meanwhile, Lynn hears disturbing news about her business partner; and Karen makes a deal with her new boss.
Mad about having to find another lawyer for her custody battle, Lynn may be biting off more than she can chew when Julian surprises her for lunch. Elsewhere, Karen finagles her way into a swanky party using her boss's invitation.
As if Lynn didn't have enough to worry about with the impending custody battle, she finds out she may face eviction when her building goes up for sale. Elsewhere, Karen learns the truth about her new boyfriend; Sophie gives her approval of her mother's love interest.
Lynn turns to an unlikely source for help when she and Maddy face a deadline and sudden financial difficulties. Meanwhile, Sophie opts to go on the school ski trip with the custody battle behind her and Nicky gone.
Lynn is charmed by a young accountant; Luke wonders if Karen and Ben's relationship is strictly business. Elsewhere, the Veronicas perform at Annabelle's sweet-16 party.
Songs: The Veronicas -- Revolution
Karen gets a tip from real-life supermodel Erin Wasson after she enters a high-profile contest; Lynn is still unsure about the age difference between her and Jeremy when he seems to have more in common with her daughters.
Karen is on pins and needles awaiting the results of the modeling contest, and Lynn may have to go it alone with the showcase. Teddy Geiger performs "For You I Will (Confidence)" at Karen's contest party.
Songs: Teddy Geiger -- For You I Will (Confidence)