Trying Season 5 Episode 5 Recap: Princess Waits for Kat as Nikki Questions Her Feelings

Trying Season 5 Episode 5 puts Princess, Nikki, and Jason through three very different emotional situations, while the episode keeps the familiar humor at the center of the story. Princess continues waiting for Kat, Nikki finally confronts her feelings for Kerry, and Jason learns that helping someone is rarely as simple as it looks. Season 5 premiered on July 8, 2026, following a two-year break, and Apple TV is releasing one episode every Wednesday through August 26. The season mainly follows the disruption caused by Kat, the biological mother of Princess and Tyler, after she unexpectedly returned to their lives. Release date: August 5, 2026 Season: 5 Episode: 5 Genre: Comedy, drama Streaming platform: Apple TV Season 5 episodes: 8 Season finale: August 26, 2026 Spoilers ahead for Trying Season 5 Episode 5. The episode begins on Princess' birthday, but her attention remains fixed on Kat. She believes her biological mother could be at a beauty salon and heads there during a driving lesson with Vic. Kat never appears, leaving Princess disappointed again, although Vic stays with her and eventually takes her inside the salon to cheer her up. Princess later writes down questions she wants to ask Kat whenever they finally meet. Her decision shows that she has not given up on getting answers, which keeps the Kat storyline moving toward another confrontation. Meanwhile, Nikki becomes increasingly confused about Kerry, her male coworker. She takes an online "Good Wife" quiz and admits that she has feelings for another man, earning a terrible score. She also tells Jason that Kerry is a man after previously allowing him to assume otherwise. That attraction quickly disappears when Nikki attends Kerry's gig with Karen. Kerry starts performing a romantic acoustic number called "The Girl From the Office," but the song suddenly turns into an awkward rap. The performance changes Nikki's perspective immediately. By the end of the episode, she retakes the quiz and scores 92%. Jason gets outsmarted while trying to help Harriet Jason spends much of Episode 5 attempting to help Harriet, a 75-year-old woman whose home is packed with possessions. She claims the objects belonged to her late husband, convincing Jason that her refusal to throw anything away comes from grief. Jason believes he has finally reached her when Harriet gives him a supposedly meaningful pen. However, his colleague Chrissy reveals that the pen belongs to her. Harriet simply invented the story to make Jason leave, then gives him the finger from her window. Elsewhere, Scott begins therapy and realizes that his endless adventures have become distractions. He later clears out much of his adventure equipment. Vic also quietly collects medication from a pharmacy, introducing another personal storyline that the remaining episodes can explore. Season 4 ended with Kat arriving at Nikki and Jason's home after Princess searched for her biological mother. Season 5 has continued exploring the consequences of that decision, especially as Princess tries to understand where Kat fits into her life. Trying Season 5 Episode 6 arrives on August 12, with three episodes remaining after Episode 5. What do you think Princess will do when Kat finally responds, and where do you think Vic's story is heading? Let us know in the comments.