Jane gets an eye-opening experience when she is tasked with writing a piece about a performance artist/activist who is speaking out about sexual assault. Kat is distracted by thoughts of Adena while trying to throw a memorable NY Fashion Week party for Scarlet; and Sutton gets into an awkward situation with Richard.

Kat struggles to get a movement off the ground and is faced with a life-changing opportunity. Sutton gets an unexpected call that threatens the progress she’s made at therapy, and Jane is faced with her biggest challenge ever at Scarlet.

Sutton and Richard’s wedding day is here, and Sutton is faced with a big decision. Jane tries to celebrate her friends while struggling to process recent discoveries. Kat’s continuing crusade against the board has unexpected and life-altering consequences.

After a season of big changes and hard decisions, the future looks bright for the women of “The Bold Type” … but it’s always full of surprises. Jane, Kat and Sutton each face huge choices and evaluate their own paths.

Kat sets out to hire someone for the social team, but is unhappy by the applicant pool’s lack of diversity. Jane, meanwhile, faces the financial realities of her freelance situation.

After an intimate moment mishap with Ben, Jane evaluates if motherhood is in her future because of her BRCA gene mutation. Kat is eager to flaunt her social media influence by partnering with a beauty brand that offers her an opportunity to be their spokesperson. Meanwhile, Sutton makes her first major fashion department decision without Oliver.

In five short love stories, Kat, Jane, Sutton, Jacqueline, and Alex confront challenges in their various relationships, bringing newfound understanding of their partners or creating irreparable rifts between them.

Kat finds herself questioning her identity as she continues to spend time with Adena. Jane is horrified when she is tasked with writing Scarlet’s sex column – especially when her story turns intensely personal. And Sutton is given an opportunity to advance at Scarlet, but questions if it’s what she really wants to be doing with her life.

Kat finds herself the victim of internet trolling when she stands up for gender inequality. Sutton thinks she may have found her dream job but worries she doesn’t have what it takes to make it work. And Jane pursues a story about a congresswoman but tries to find a different angle to make her voice heard.

Jane crosses paths with Pinstripe, who inspires her to try a new style of writing. Meanwhile, she learns something new about Ben. Adena reluctantly brings Kat out to meet her friends, and Kat quickly immerses herself in the New York lesbian scene. Sutton fights for an in with a well-connected influencer named Brooke.

Jane is thrilled when her sexual assault article for Scarlet is nominated for a prestigious journalism award. Determined to prove herself to Jacqueline, Jane jumps at the chance to write a follow-up piece, until the story takes an unexpected turn. Kat struggles with whether to tell Adena a secret and Sutton is given a challenging assignment – styling Richard’s date.

Jane decides to throw Sutton an epic bachelorette party, but the bride can’t quite bring herself to enjoy the festivities. Kat learns surprising info about RJ, which leads her to question the company’s morals. Jane gets career news while facing some devastating personal issues.

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.

Jane faces unexpected performance reviews that shake her confidence in The Failing Feminist. Sutton’s attempts to move on from her divorce are thwarted by other’s opinions, and Kat reunites with Adena, who has a secret.

All eyes are on Jane as she and Jacqueline combat a public inconsistency in her latest story. Kat runs into an old friend, sparking a new idea. Alex uses his podcast to make a statement. Sutton gets a career win but a personal blow.

Sutton is flustered when someone at Scarlet has the wrong impression of her professional background. Jane is determined to prove she can have a friends with benefits relationship without feelings getting in the way. And Kat and Adena continue growing closer.

Jane is stunned when the subject of her latest article, a woman who left a finance job to become an exotic dancer, threatens to sue Scarlet – and Jane. Sutton is excited when she thinks she’s making a step forward in her career. Kat questions whether she is ready for a real relationship with anyone, especially in light of recent events with Adena.

As rumors of layoffs at Scarlet sweep through the office leaving everyone unsettled, Jane learns of a potential opportunity at a rival publication. Sutton is given a big opportunity when a coworker buckles under pressure. Kat is tasked with organizing a “Readers Night” for Scarlet, but is distracted by thoughts of Adena – leading to a big decision. And Jane talks Sutton and Kat into joining her on a dating app.

Jane, Sutton, Alex, Pinstripe and Jacqueline are all trapped in the Scarlet offices due to a massive traffic jam. Forced to spend time together, Jane reexamines her feelings for Pinstripe. Sutton makes a surprising move. And when she learns Adena is leaving New York, Kat makes an impulsive decision.

Jane is excited to publish her first big piece for Incite, especially since she’s writing about a female CEO she admires, and she knows Jacqueline will be reading it. Sutton is thrown when a new corporate policy seems to give her and Richard the green light on their romance. And Adena grows frustrated when Kat seems too eager to flaunt their burgeoning relationship.

Believing it shouldn’t matter, Kat bristles when Alex recommends she highlights that she is black in her company bio. However, while introducing her parents to Adena, Kat is forced to confront how her avoidance of labels has affected her life. Sutton is horrified when she discovers her fellow fashion assistants think she was asked to organize a photo shoot featuring “honorable men” for reasons other than her talent. And Jane tries to defend herself after the fallout from her Incite article, which doesn’t go as planned.

The girls take a trip to Sutton’s hometown and meet a few important figures from her past. Meanwhile, Jane struggles with planning for her future, and Kat feels a rift in her relationship with Adena. Guest starring Billy Magnussen.

Kat is faced with a past regret when she crosses paths with a closeted singer who asked for help 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 Magazine brings in Patrick Duchand to run the digital branch, effectively knocking Jacqueline down to only running the print magazine. Meanwhile, Jane has picked her guy, but is frustrated that a man is put in charge of a women’s magazine. Kat struggles to keep up happy appearances on social media and as a speaker at the Scarlet Summit, while secretly suffering heartache, and Sutton and Richard enjoy their romance in the limelight and discuss moving in together.