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.

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.

When Jane and Jacqueline’s exposé makes an impact, Jacqueline takes a hard look at how she can make Scarlet an industry leader that practices what it preaches. Sutton celebrates the end of her design seminar with a fashion show but surprises herself with the results. Jane deals with an emotional fallout amidst a career high. Kat makes a choice not to run from her problems anymore.

Jane stumbles on the scoop of a lifetime, but Jacqueline turns down the pitch when her impending 10th-anniversary gala and continued power-struggles with Patrick force her to contemplate her future with Scarlet. Sutton preps a design seminar application for Oliver’s recommendation, but he remains distracted by things in his personal life. Kat decides to run for City Council but reconsiders when she learns what the opposition might spin about her past.

Sutton’s professional dreams come true when she jets off to Paris for Fashion Week, but while there she gains a new perspective on her situation. Jane moves forward with her fertility plan until she learns surprising news about her options and is faced with Ben and Pinstripe’s different solutions. Kat faces pressure from Jacqueline to make their Paris party a success while attempting to reset her relationship with Adena.

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.

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.

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.

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, Kat and Sutton, all overwhelmed with monumental work decisions, seek clarity in an unorthodox way.

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.

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.

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.

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.

The Scarlet email hack brings up memories of the trio’s first meeting four years ago, reminding them that together they can overcome anything.

When Kat beings to doubt herself on the eve of her election, an unexpected person gives her the reassurance she needs. Jane and Jacqueline are confident about their workplace harassment investigation and decide to take action. Sutton coaches Carly through a difficult situation at school.

Sutton visits her hometown, but falls into a familiar pattern while there. Jane finds a big story, but it could have serious ramifications for Jacqueline. Kat is reluctant to share her new romance with Jane and Sutton.

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 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.

When Jane discovers that Sutton has been hiding a gun in the apartment, the girls realize they have polar opposite views on the subject. Meanwhile, Adena shocks Kat with her latest suggestion.

Kat and Adena need to work together on a Scarlet project, which becomes tense when Adena learns about Kat’s recent romantic relationships. Sutton earns her first solo styling gig, hoping it leads to being a fashion influencer. Jane makes a decision about her health concerning her BRCA-1 status.

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. Oliver comes face to face with his ex.

Jane’s in-depth look at millennial weddings comes to a screeching halt when she uncovers a secret about Jacqueline. Overwhelmed by her current assignment and against uniforms of all kinds, Sutton decides to focus her energy on helping Carly take on her school uniform policy, without running it by Oliver. Meanwhile, Kat thinks she can handle uncomplicated dating, only to find it’s more complicated than she thought.

Richard is determined to get to know Sutton’s friends outside of the office and invites the girls to dinner, but things don’t quite go as planned. Sutton attempts to network with a new social circle by attending a high tea. While on a date with someone else, Jane comes to a realization about Pinstripe; and Jacqueline is forced to intervene when Kat’s new staffer keeps damaging Scarlet’s social media presence.

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.

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.

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 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. Sutton starts to feel she’s going backward in her career and looks for a way to improve her value to Scarlet. Jacqueline’s new situation at work leads to tension with her husband.

Jane volunteers to write a story about a sex club in hopes of proving she is ready for the next step in her career. Kat’s latest crusade to save a female-oriented sex toy company could lead her to begin dating again, while Sutton has doubts about how to kick off her plan to get promoted. Meanwhile, Alex struggles with his new platform at Scarlet.

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.

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.

Newly promoted writer Jane is unsettled when Jacqueline assigns her a big story – writing about why her ex broke up with her. Kat chases a story about outspoken photographer Adena, but is confused by her strong connection to the woman. Meanwhile, Sutton tries not to feel left behind by her best friends as she still toils in the assistant ranks. But she shocks them when they uncover a major secret Sutton has been keeping – her scandalous affair with lusted-after Scarlet magazine lawyer Richard.