Don't Trust the B---- in Apartment 23

June relocates to Manhattan for a promising job and a company-provided apartment, only to find both vanish unexpectedly. She takes a position at a coffee shop and moves in with Chloe, an engaging but morally flexible roommate.

June finds dating increasingly complicated after agreeing to let Chloe set her up, while James struggles to break free from his Dawson persona as he begins teaching an acting class.

June, already stretched thin with a high-pressure internship and two jobs, takes on even more work until she's forced to deal with the fallout from one of Chloe's chaotic, ill-conceived plans. At the same time, James is excited to star in a body-swap film alongside Kiernan Shipka and begins preparing intensively for the role.

June is upset upon receiving a wedding invitation meant for her and her ex-fiancé, prompting Chloe to help her regain confidence—perhaps more than intended.

June tries to earn extra money by selling her homemade jam, but things escalate when Chloe joins in and expands the business. At the same time, James introduces his new fashion line, a brand of extremely narrow jeans he names "Beek Jeans.

Chloe attempts to guide June in embracing her sexual confidence through casual relationships, but Chloe's past comes back to haunt her when a leaked sex tape with James threatens his public image and performance on *Dancing with the Stars*.

June tries to fit in with Chloe's social circle and keep up with her wild party lifestyle, which has become so iconic it's even inspired a Japanese comic book. At the same time, James becomes increasingly frustrated upon learning that Dean Cain's "Dancing with the Stars" dressing room is larger than his own.

James ignores Chloe's caution and follows June's suggestion to attempt a Dawson's Creek reunion, leading to unexpected revelations and encounters with former TV stars along the way.

June, who loves Halloween, is excited to enjoy it freely now that she's single, but her enthusiasm wanes when she learns that Chloe's annual Halloween pranks could become dangerous. Determined to prevent any real harm, June sets out to stop Chloe. At the same time, James, haunted by childhood fears of Halloween, hosts his traditional "Positivity" Party to counter the holiday's spooky vibe.

June becomes fixated on the *PEOPLE* magazine Sexiest Man Alive issue, but Chloe challenges her to think independently about beauty standards. Determined to make a point, Chloe boldly infiltrates the *PEOPLE* offices to campaign for James to be named this year's honoree. As a result, James becomes excited about the possibility, and June finds herself unexpectedly drawn to him.

Chloe and June have opposing views on Thanksgiving, leading to an uneasy plan when June, unable to afford her own trip, agrees to join Chloe at her parents' home under awkward circumstances. Meanwhile, James's attempt to gain publicity by volunteering at a celebrity soup kitchen backfires when he and Luther are forced to do real work.

Chloe introduces June to the art of networking through late-night drinking in the financial district, leading to an unexpected job opportunity for June when Chloe impresses a young broker with influential connections. However, the offer comes with difficult conditions that force June to make a tough choice. At the same time, James faces a major challenge when he is partnered with an inexperienced and frustrating professional dancer.

James arrives in Los Angeles ready for the "Dancing with the Stars" premiere, while Chloe takes advantage of his absence by turning his penthouse into the setting for one of her elaborate schemes. June attempts to guide Chloe toward honesty, but her own convictions are tested. Meanwhile, James's entrance on stage astonishes everyone.

June is anxiously waiting to hear about a job opportunity while James struggles with his own setbacks, leading Chloe to plan an impulsive weekend trip to the Hamptons in an attempt to lift everyone's spirits. While Chloe intends for the trip to be a wild party and a chance to meet the mysterious host, the events of the weekend take a more introspective turn than expected.

June begins her new job at Harken Financial with a mix of anxiety and anticipation. She finds the experience unexpectedly positive, especially after bonding with a kind and supportive co-worker, Fox Paris. However, her friend Chloe cautions her about trusting Fox too easily, while Mark seeks James's advice on how to confess his growing feelings for June.

June and Chloe attend their first tenants' meeting after new neighbors move in, but their behavior causes a disruption. June tries to rein in Chloe's antics to avoid being seen as troublemakers in the building. However, Chloe's growing interest in Mark and James's interference complicate June's efforts to maintain a respectable image.

June tries to bond with Chloe, but Chloe remains cautious about forming close friendships due to past experiences with manipulative girls. Instead, June grows close to a group of women in her Pilates class whose behavior mirrors what Chloe fears. At the same time, James attempts to improve his public image by mentoring a troubled youth, but their first meeting reveals a mutual lack of understanding between them.

June, encouraged by Chloe, decides to participate in a reality dating show she and Mark are obsessed with. Their friendship is tested when both end up pursuing the same man, leading to a series of dating challenges orchestrated by James to determine who will win his affection.