Fresh off a wild night with a new fling, Kat considers flipping the script on preconceived gender roles in the bedroom. Jane's tapped to speak at a wellness seminar, but the appearance of a sudden feminine health problem has her feeling like a fraud. Sutton tries to earn the respect of Richard's mother while finding sponsors for her Instagram, and Alex challenges his notions about masculinity while dating a high-powered woman.

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.