Quinn brings Rachel back from self-imposed "exile" in a desperate attempt to keep "Everlasting" afloat following the PR nightmare of the previous season; Silicon Valley mogul Serena becomes the new season's female "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. Rachel opens up about her past to Dr. Simon. One of the contestants reveals the real reason why he came on the show.