‘Trying’ Season 5 Episode 5 Ending Explained: Kerry’s Disastrous Song Leaves Nikki Cringing

Apple TV’s cherished family comedy ‘Trying‘ has entered its fifth season, focusing on rebuilding Nikki and Jason’s lives after Kat’s unexpected return threatened their stability. As we reach the fifth episode, the show has shifted from its earlier crisis mode to more intimate storylines that resonate deeply.

Following the fallout from Scott’s fabricated Atlantic crossing story revealed in Episode 4, Episode 5 centers on Nikki, portrayed by Esther Smith, and the mounting tension between her professional life and her marriage to Jason, played by Rafe Spall. The episode, titled “Ick,” begins with Nikki eagerly anticipating a colleague named Kerry’s performance, unaware that her feelings are about to take a surprising turn.

Nikki had been excited about attending Kerry’s gig, especially after discovering he wrote a song called “Girl from the Office” dedicated to her, hinting at potential romantic tension. When the day arrives, Jason decides to join her, eager to meet the man his wife has been discussing, completely oblivious to the mix-up regarding Kerry’s gender.

However, any spark Nikki felt for Kerry quickly dissipates as his performance begins. The attraction she had built in her mind vanishes when the second half of his song transforms into something that evokes secondhand embarrassment rather than romance.

Esther Smith shared her experience filming this scene, admitting she was unprepared for how it would unfold. Upon reading the script, she remarked, “Oh, he’s rapping, is he?” The moment Kerry’s performance shifts to rapping creates such an overwhelming sense of ick for Nikki that she starts recording video to remind herself just how off-putting it was.

This secondhand embarrassment serves a larger purpose in the episode’s narrative. Smith noted that the entire sequence places Nikki in a genuinely challenging position, creating real tension in her marriage, ultimately strengthening her bond with Jason instead of driving them apart.

Before the disastrous performance completely sours the mood, the episode allows Nikki and Kerry a final moment of genuine connection. They share a lighthearted interaction when Nikki sneaks into the office as part of a mousetrap plan, leading Kerry to invite her to his upcoming concert.

Still troubled by not revealing the full truth about Kerry’s gender to Jason, Nikki tries to prevent her husband from joining her at the gig. However, once Kerry’s lackluster singing takes center stage, any tension surrounding that secret dissipates, as his performance erases whatever interest Nikki had initially felt.

Smith suggested that this pattern, where new challenges ultimately bring Nikki and Jason closer rather than driving them apart, has become a recurring theme throughout the series. Whether Nikki will come clean to Jason about her fleeting crush remains an open question as the season progresses, though Smith has indicated that infidelity is not where this storyline is headed.

With the Kerry storyline now largely resolved and the show’s second half still addressing the aftermath of Scott’s Atlantic Ocean saga, ‘Trying’ appears set to continue exploring smaller, character-driven narratives rather than prolonged family crises in the upcoming episodes.

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