Scarlet reels over their new dynamic, forcing everyone to adjust, while Jane tries to cope with the changes to Jacqueline's role at the magazine, and Sutton takes stock of her position at Scarlet, as Richard considers a world outside it.
Kat 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, while Sutton and Richard's long-distance relationship hits a snag.
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. Meanwhile, Jacqueline's work situation leads to tension with her husband.
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, and Sutton has doubts about how to kick off her plan to get promoted.
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, and Kat finds uncomplicated dating more complicated than she thought.
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.
Kat and Adena need to work together on a Scarlet project, which becomes tense when Adena learns about Kat's most recent relationship; Sutton takes a big risk, but is disheartened when it goes awry; Jane makes a big decision about her future.
Jane is overjoyed that 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 and Sutton dive into wedding plans.
Jane decides to throw Sutton an epic bachelorette party, but the bride can't quite bring herself to enjoy the festivities; Kat learns surprising information about RJ; Jane gets career news while facing some devastating personal issues.
Sutton and Richard's wedding day is here, and Sutton is faced with a big decision. Jane tries to celebrate with her friends while struggling to process recent discoveries.
Three months after surgery, Jane returns to Scarlet with new editorial duties; Kat faces a hard truth when she's forced to take some responsibility; Sutton goes to bat on her first shoot and gets some shocking news that upends her world.
A blizzard hits New York City, and Kat is trapped at her new job with her nemesis; Sutton struggles to balance her career and relationship; Jane tries to emulate Jacqueline's leadership with her new staff.
Sutton grapples with her complex reaction towards the massive changes in her life; at Kat's urging, Jane starts dating again; Kat plans her next move as she faces financial insecurity and turns to Alex for help.
Jane isn't comfortable in her post-surgery body, but a visit from her dad may change her outlook. Sutton and Richard make plans for the future. Kat tries to move forward at work with a podcast, but her first episode comes with a price.
Kat, Jane, Sutton, Jacqueline and Alex confront challenges in their various relationships, bringing newfound understanding of their partners or creating irreparable rifts between them.
Sutton falls into a familiar pattern when visiting her hometown; Jane comes across a huge story that could have consequences for Jacqueline; Kat feels reluctant to share her new relationship.