The initial plan to reveal Liza's actual age as a form of protest against ageism is dismissed by Quinn when published news hint that it was Kelsey who kept a secret relationship with Charles, which Diana believes, forcing Liza to reveal to everyone in Empirical that she is the one who maintained an affair with him. As a result, Diana begins searching for a new job, which leads Kelsey and Liza to perform Dolly Parton's song "9 to 5" with her as a way to convince her to stay. Now as Empirical's publisher, Kelsey takes notice of its financial crisis. After taking a paternity test, Josh learns that he is Clare's baby's father. Charles buys a new bed for Liza's apartment and, after facing his free time, decides to meet with Zane to ideate a project. Charles and Liza say "I love you" to each other for the first time.

Josh worries about his ability as a father and Liza reassures him. After a pre-evaluation with a group of women about Claw, Quinn's book, the reactions are negative and Kelsey meets with her to postpone the release; Quinn reveals that she is running for Senate of California, thus making impossible to postpone the publication. They then decide to publish Claw and, in case of commercial failure, Quinn will withdraw from the company. Zane asks "not to be friend" of Kelsey, indicating a romantic relationship. Charles apologizes to Diana for having abruptly left Empirical. Lauren sends Diana and Enzo's love story to a newspaper. Diana and Enzo have an argument after he learns that she still has romantic affection for Charles. She then decides to continue with the publication of their love story as a way to apologize, successfully. Liza and Charles decide to leave their professional lives aside when they are together. During the baby's gender reveal party, Clare begins labor and gives birth to a girl inside an Uber.

After witnessing the birth of Clare's baby, Maggie develops a fear of vaginas; Lauren introduces her to a help group on the subject and Maggie has a date with Beth, the group's leader. Clare and Josh decide to divorce after they both question the possibility of liking each other again. Kelsey and Liza learn that Quinn bought several editions of Claw and ordered Chinese Twitter bots to leverage the book's success. Millennial receives Audrey Colbert, an accused murderer who becomes a celebrity through a podcast and is willing to publish her truths. Redmond promises exclusivity for Kelsey; however, after the disclosure of Claw's adulterations, Colbert talks with other publishing houses. During a press conference, Quinn is pressured about the book, and her Senate campaign is unveiled by Kelsey. Redmond reveals that a new imprint named Mercury has offered a good proposal to Audrey and the publisher is Zane. Liza then has an epiphany and realizes that Charles has sold one of his properties to help his "secret project" with Zane.

Kelsey discovers that Charles is working with Zane at the Mercury publishing house. She screams with Zane and Charles during a meeting they would have with Bronwyn Madigan, an author who considered leaving Millennial. The video of Kelsey screaming goes viral. Madigan decides to remain at Millennial, but agents from several other authors contact the company wanting to cease contracts and move to Mercury. Due to stress, Kelsey begins to lose several strands of hair. Maggie and Beth's relationship progresses as Josh realizes how present he wants to be in his daughter's life.

Lauren creates an Instagram profile for Gemma, Josh's baby. Both take advantage of the success and influence of the profile to get various products for free. Millennial suffers from another possible publication being taken by Mercury. The competition between Charles and Liza gradually increases to the point where they argue over Millennial's downfall. Kelsey questions Liza's loyalty. Diana and Kelsey go axe throwing and drinking. When the restroom is found to be out of order Diana is forced to urinate in the street and is cited on grounds of public urination but she and Kelsey are then arrested when Kelsey accidentally waves one of the axes she's still holding in the police officer's face but are bailed out by Enzo. Charles appears by surprise in Liza and Maggie's apartment and sees Liza next to Josh and Gemma. Liza goes after him and they argue because Charles affirms that, in the end, both Mercury and Millennial are his property.

Maggie decides to paint the ceiling of the apartment and, in the process, ends up getting stuck upside down. She asks a front neighbor for help and the man masturbates watching the scene. She breaks free after reaching for a switchblade and cuts the rope. During a recording session of Audrey's narration, Zane ends up leaving a microphone on, comments to Kelsey that he finds Audrey guilty of what she is accused of; she listens and leaves the studio enraged. In an attempt to get Travis Jason, author of a nonfiction book on drug use for work, Charles and Liza decide to go to a "medicinal" retreat hosted by Jason. There, the two meet Josh, who is Travis's friend. Liza, under "not LSD", reveals her feelings about Josh and Charles to a nurse and hallucinates a tango dance with the two. After the retreat, Charles decides to sell Mercury to Kelsey for one dollar so he can work alongside Liza and stop fighting with his family, which are Kelsey, Liza and Diana.

Zane and Charles are back at Millennial and Kelsey has a difficult time as she is still intimidated by her mentor, Charles. Liza finds an unfinished manuscript in some of Charles old boxes and pitches it to Kelsey, however it turns out that Charles wrote the book when he was younger and does not want to publish it. Charles and Liza decide to not do things they do not like together after having uncomfortable conversations at events, and even run away from one. Liza and Josh reconnect for a bike ride. Elsewhere, Diana attends Enzo's niece's baptism, where Enzo's ex is the god-mother with Enzo as god-father. Enzo's sister tells Diana that none of Enzo's relationships last more than a year, and when she asks him about it, in a surprising turns of events, Enzo proposes to Diana outside the church, realizing how much she means to her, she says yes.

Liza goes to Charles' daughter's school to drop off a book report, wearing Pauline's jacket as she had no clothes at Charles' house. At the school she meets Pauline, they decide to start afresh and get lunch. Pauline even asks the school to register Liza. On hearing about this, Charles asks Liza to move in with her. At lunch Pauline asks Liza to help her with her new book and in return Liza asks her to be Millennial's author at the Debutante Ball, a big publishing event. On another visit to the school, Pauline gets to know Liza's real age. Feeling hurt and betrayed, she reveals Liza's secret in front of everyone at the Debutante Ball. Diana tries to stand up to her, but on getting to know the truth, runs out and faints on the road. At the hospital, Charles and Liza decide to postpone moving in together as Pauline wants to reconsider the custody agreement, and the time is not right. Diana who had earlier implied she wanted Liza to be her maid of honor, although still hurt, reconciles with Liza after realizing how much she means to her.

Millennial deals with fall outs after the revelation of Liza's real age. Infinitely 21, a clothing brand with whom Millennial had a deal to sell books in store, cancelled their deal. However after Liza's speech to them about how being millennial is not about age, but about how you feel, they unfroze their deal and also wanted Liza to be a model for their spring collection. Josh walked in on Liza's photoshoot and a candid picture of his and Liza's was chosen by Infinitely 21 for their campaign. Elsewhere, Zane and Kelsey sort things out and confess their love for each other. Maggie dates a man but does not enjoy the experience. Quinn asks Liza to join her in a talk about corporate ageism with New York 1 where Liza tells the anchor that Quinn knew about her real age from before. However, while shooting Quinn says she found out about it only a week back, a lie that could potentially affect her election campaign. She then asks Kelsey to fire Liza, but Kelsey refuses. It is later revealed that Quinn has pulled her funding and Millennial is broke once again.

Kelsey and Charles fly to Chicago to meet with the only potential investor left. Kelsey convinces them that her social media is one of the important reasons for Millennial's success and asks them all to follow her. Liza sees the Infinitely 21 campaign and asks Kelsey to stop Charles from seeing it, but when she learns that the campaign is going national, she flies to Chicago. Kelsey and Charles celebrate winning the investment and so Liza waits to break the news to Charles. In an inebriated state, Kelsey posts an indecent story to Instagram which she aimed to send to Zane, and falls asleep. The next morning, she becomes aware of her mishap and the investors say they still want to invest, but with Charles as publisher. Charles tries to convince them but Kelsey steps down as publisher. Charles is surprised that Liza flew to Chicago just to tell him about the Infinitely 21 ad campaign and Liza decides she won't see Josh anymore. In further news, Josh learns that Clare has been offered a promotion at Google, but the job is in LA. Not wanting Clare to take the job and Gemma, and trying to capitalise on the Infinitely 21 campaign, he convinces them to enter into a partnership with Inkburg. Diana, Liza, and Lauren go dress shopping for Diana's wedding.

Kelsey announces to the entire office that Charles is back as publisher and seems to be fine. However when Charles questions some of her decisions as publisher, she does not know what to do. At the office, everyone is watching a remixed version of Kelsey's social media clip, when Liza scolds everyone and says Kelsey was a hero. This makes Kelsey agree to give a talk to school girls about how to be a SHero and avoid social media pitfalls. Kelsey and Zane break up again. Liza writes a handwritten letter to Josh about not wanting to see him again. The girls throw Diana a surprise bachelorette party. Afterwards they go to Inkburg, because Diana wanted to make a drunken mistake, but backs out in the end. Josh confronts Liza about her letter and forces her to say she loves Charles more than him. When she does, Josh doesn't believe her and claims she is lying. In the end, Kelsey is seen penning down a letter to Charles that it is time for her to move on.

When Kelsey tells Liza she's left her resignation letter on Charles' table, Liza runs to stop him from seeing it but Kelsey tells him she's leaving and they share an emotional goodbye. Kelsey is thinking about starting her own publishing company. Zane advises her not to do it, but after some unexpected advice from Maggie she approaches Quinn and manages to convince her to invest. Liza and Charles run into Quinn who tells them of this development, Charles then offers Kelsey a stake in the company and a seat on the board at the wedding, because she is family. Enzo's uncle makes an ice statue of a fish (a trout) coming out of a toilet to signify Diana and Enzo's relationship, Diana hates it. However Lauren sits on it without underwear and gets stuck, hence destroying the sculpture. Diana and Enzo get married. Kelsey and Zane hold hands at the ceremony. Infinitely 21 wants to license the tattoo that Josh gave Liza, but when he asks her whether she'd be okay with it, Liza remembers the time she got it and refuses. After inviting Liza and Caitlin to join him for a vacation with him and his daughters, Charles takes a big step in his relationship with Liza. At the wedding, while dancing to "their" song, he proposes to Liza. Before Liza can respond, Kelsey says yes to Charles' earlier offer and the episode ends in a cliffhanger.