‘Trying’ Season 5 Episode 5 Ending Explained: Kerry’s Disastrous Song Gives Nikki a Serious Case of the Ick

Apple TV’s beloved family comedy ‘Trying‘ has spent its fifth season quietly rebuilding Nikki and Jason’s world after Kat’s unexpected return threatened to upend everything they’d built together. Five episodes in, the show has settled into a gentler rhythm, trading the season’s earlier crisis mode for smaller, more personal storylines that hit just as hard in their own way.

Following the fallout from Scott’s fake Atlantic crossing story revealed in Episode 4, Episode 5 turns its attention squarely back to Nikki, played by Esther Smith, and the growing tension between her work life and her marriage to Jason, played by Rafe Spall. The episode, titled “Ick,” picks up with Nikki genuinely excited about seeing a colleague named Kerry perform outside the office, unaware that her feelings are about to take a dramatic turn.

Nikki had been looking forward to attending Kerry’s gig, especially after learning he’d written a song called “Girl from the Office” dedicated to her, a detail that suggested real romantic tension building between the two. When the day of the show finally arrives, Jason decides he wants to come along too, hoping to finally meet the man his wife had been talking about, all while remaining completely unaware of the gender mishap surrounding who Kerry actually is.

Whatever spark Nikki felt toward Kerry evaporates almost instantly once his performance gets underway. The attraction Nikki had built up in her mind vanishes the moment the second half of his song kicks in, turning what should have been a romantic gesture into something closer to secondhand embarrassment.

Esther Smith spoke about filming the scene, admitting she wasn’t quite prepared for how the moment would actually play out on the page. She recalled her reaction upon first reading the script, saying, “Oh, he’s rapping, is he?” She went on to explain that the moment Kerry’s performance turns into rapping gives Nikki such an overwhelming ick that she starts recording video specifically to remind herself later just how off-putting the moment truly was.

That secondhand embarrassment ends up serving a bigger purpose within the episode’s story. Smith noted that the entire sequence puts Nikki in a genuinely difficult position that creates real tension in her marriage, one that ultimately strengthens her bond with Jason rather than driving a wedge between them.

Before the disastrous performance fully sours things, the episode does give Nikki and Kerry one last moment of genuine connection. The two share a fun, lighthearted moment when Nikki sneaks into the office as part of an ongoing mousetrap plan, and Kerry invites her to attend his upcoming concert as a direct result of that interaction.

Still bothered by the fact that she hadn’t told Jason the full truth about Kerry’s gender, Nikki tries unsuccessfully to stop her husband from tagging along to the gig. Once Kerry’s underwhelming singing takes center stage, though, any tension surrounding that secret dissolves almost entirely, since his performance ends up erasing whatever interest Nikki had developed in him in the first place.

Smith suggested that this pattern, where a new challenge ultimately draws Nikki and Jason closer together rather than pulling them apart, has become something of a throughline across every season of the show. Whether Nikki chooses to come clean to Jason about the crush she briefly harbored remains an open question as the season continues, though Smith has indicated that infidelity isn’t part of where this particular storyline is headed.

With the Kerry storyline now largely defused and the show’s back half still weaving through fallout from Scott’s Atlantic Ocean saga, ‘Trying’ looks poised to keep leaning into smaller, character-driven stories rather than sustained family crisis for its remaining episodes.

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