Trying Season 5 Episode 6 puts Nikki and Jason’s relationship under the spotlight during a Halloween date night, while Princess finds herself in an increasingly uncomfortable situation away from home.
Titled “Halloween,” the episode turns a small disagreement between Nikki and Jason into the honest conversation they have avoided for several episodes, while Princess gets another complicated lesson about Kat and the kind of parent she can be.
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- Episode: Trying Season 5 Episode 6
- Title: Halloween
- Release date: August 12, 2026
- Runtime: About 25 minutes
- Genre: Comedy
- Streaming on: Apple TV
- Season length: Eight episodes, with the finale scheduled for August 26
Trying Season 5 Episode 6 recap
Spoilers ahead for Trying Season 5 Episode 6.
Nikki and Jason plan to spend Halloween watching The Ring, but their date starts going wrong after Nikki catches Jason looking at another woman while they buy snacks. Jason denies it and claims he was actually watching a child nearby, turning a minor moment into an argument that follows them to the cinema.
They eventually return to the store and check the security footage. The video appears to prove Nikki right, although Jason continues trying to explain what happened. The disagreement finally pushes Nikki to admit why Jason’s denial bothers her so much.
Nikki tells Jason about Kerry and admits that she developed a crush on him. The storyline has been building through Season 5 as Nikki struggled with her attraction while keeping it from Jason. Jason handles the confession surprisingly well, and after seeing Kerry’s rap video, he reassures Nikki that their relationship is okay. By the end of the episode, Jason also admits that he really was looking at the woman in the shop.
Princess’ Halloween night gets dangerous
Princess attends a party with her friend, but the night quickly becomes uncomfortable when several older men begin watching them. One man approaches Princess, while another appears to help before revealing that he also has questionable intentions. Princess recognizes the danger and leaves to find her friend.
She eventually calls Kat for help. Kat arrives, finds the girls, cuts the party’s power while retrieving Princess’ broom, and uses the confusion to get them outside safely. On the bus home, Kat explains that she has been trying to sort out her life by opening a bank account and finding work.
The scene continues Season 5’s central story around Kat’s return. After arriving back in Princess and Tyler’s lives, their biological mother has forced Nikki, Jason and the children to reconsider where she fits within their family.
Meanwhile, Scott remains withdrawn after therapy, leaving Karen worried that she pushed him toward changes he was not ready to face. His storyline remains unresolved as the season moves toward its final two episodes.
Trying Season 5 Episode 6 ends with several relationships in a different place, especially Nikki and Jason after finally discussing Kerry openly. Episode 7, “Tuscany,” arrives on August 19 and sends Nikki and Jason away while problems continue developing back home.
What did you think about Nikki’s confession to Jason and Kat coming to Princess’ rescue? Let us know in the comments.
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