In a desperate attempt to keep Everlasting afloat following the PR nightmare of the previous season, Quinn brings Rachel back from self-imposed "exile." Together they must manage Serena, a Silicon Valley mogul and this season's suitress.

After a poker game with the contestants leaves Serena the sore winner, Chet decides to teach her how to be the woman that all men want to marry. Quinn makes a connection with one of the contestants after meeting Chet's new swimsuit model girlfriend.

A patriarchal group date infuriates Serena, who refuses to heed Chet's advice on how women should act any longer. After discovering a big secret that Quinn has been hiding, Rachel opens up about her past to Dr. Simon while one of the contestants reveals the real reason why he came on the show.