Jane is overjoyed when her brother Evan comes to town, and she introduces him to Ryan. Adena turns to Kat for help in dealing with RJ, which causes more trouble between Kat and the board. Richard returns from San Francisco, allowing him and Sutton to dive into wedding plans.
Kat considers her feelings on preconceived gender roles in the bedroom; Jane feels like a fraud when asked to speak at a wellness seminar while struggling with a sudden feminine health problem; Sutton tries to bond with Richard's mother.
Jane's story on millennial weddings comes to a halt when she uncovers a secret about Jacqueline; Sutton helps Carly take on her school uniform policy without running it by Oliver; Kat finds uncomplicated dating more complicated than she thought.
Jane volunteers to write a story about a sex club; Kat's latest crusade to save a female-oriented sex toy company could lead her to begin dating again; Sutton has doubts about how to kick off her plan to get promoted.
Kat goes out of her way to help a transgender runner get into the New York City Marathon, while Jane and Ryan try a different kind of marathon to rebuild their relationship; Jacqueline's new situation at work leads to tension with her husband.
Kat is faced with a past regret when she crosses paths with a closeted singer who had asked for help in coming out. Jane has her first mammogram and spirals into anxiety waiting for the results – and how Ryan fits into it. Sutton and Richard’s long-distance relationship hits a snag. And the trio discovers a secret about one of their coworkers.
Scarlet reels over their new dynamic, forcing everyone to adjust. Jane tries to cope with the changes to Jacqueline’s role at the magazine, and joins forces with Kat and Sutton to make it clear how much she means to them. Sutton takes stock of her position at Scarlet, as Richard considers a world outside it. And Kat butts heads with RJ Safford over response to the new direction of the magazine. MORE -LESS