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.

Rachel is forced to come clean to Serena. Quinn approves Jay's idea for a new show, but must make a potentially dangerous deal with one of the contestants. Rachel revisits a trauma from her dark past and uncovers distressing news.

Quinn and Jay's new show pitch to Gary does not go as planned. Rachel confronts her father about her past and rescues him from her mother's control. Serena learns a contestant's secret. Jay's arrangement with Alexi becomes even riskier than before.

Under the watchful eye of Dr. Simon, Rachel attempts to help her father come off his medication, forcing her to make a painful decision. Jay delivers difficult news regarding his new show. Quinn and Chet take matters into their own hands with two of the contestants, making Everlasting gold.

In the Hometown Date episode, Rachel pushes Serena to make a choice which sends her down a path of uncertainty. To Rachel's horror, Quinn pulls a dangerous stunt which forces Serena to save the day. Chet gets a tempting proposition from Gary.

Rachel confronts her mother while Serena gets ambushed someone from her past, threatening her relationships with the remaining contestants. Chet struggles with Gary's offer.

Rachel helps Serena navigate the home stretch and narrow the suitors down to two at Chet's lifetime achievement gala. However, clashing opinions cause a public fight and Quinn's plan to take down Gary takes a turn.

A life-changing offer from Serena and a shocking discovery about Dr. Simon drive Rachel to strongly question her future at Everlasting. Chet makes an astonishing confession while Quinn takes one final swing at Gary