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.
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.
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.
In promoting Scarlet's breast health awareness campaign, Kat tries to be bold with her message, but is left wondering whether her competitive nature is hurting her cause. Jane confronts past issues and current anxieties when she is tasked with writing a controversial piece about BRCA gene testing. Sutton is determined to excel at her tasks at hand, but when things fall apart, it's Alex who rushes to her rescue.
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.
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 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 New York Fashion Week party; Sutton gets into an awkward situation with Richard.