New jobs, new chapters, and one seriously shocking discovery — Trying Season 5, Episode 2, “First Days,” proves once again why this Apple TV+ comedy hits different. Nikki and Jason step into fresh phases of their lives while Karen’s world quietly tips upside down, and the result is classic Trying: awkward, sweet, and deeply human.

Trying S5 E2

Detail	Information
Episode Title	First Days
Release Date	Wednesday, July 15, 2026
Platform	Apple TV+
Creator	Andy Wolton
Lead Cast	Esther Smith, Rafe Spall
New Addition	Colin Morgan as Kerry

What Happens in Episode 2

Nikki finally starts her new job in the travel industry, and it doesn’t take long before her handsome new colleague Kerry catches her eye — an unexpected wrinkle for a couple already dealing with Kat’s disruptive return. Meanwhile, Jason begins his path toward becoming a social worker, inspired by his old adoption officer Penny. Their “first days” unfold with the show’s trademark blend of cringe and heart. Elsewhere, Nikki’s sister Karen stumbles onto a discovery that shakes up her already chaotic household, adding another emotional thread to a season that’s clearly setting up bigger payoffs ahead.

Why This Episode Works

What makes Trying special is how it finds comedy in ordinary mess rather than manufactured drama. Nikki and Jason, brought to life by two leads whose chemistry has anchored the show since it first arrived on Apple TV+ in 2020 as detailed on its Wikipedia page, continue to feel like real people fumbling through real life rather than sitcom archetypes. Episode 2 leans into that strength, using small, believable moments to build toward the season’s bigger emotional arcs.

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Catch up on the season premiere and everything leading into Episode 2 with our full breakdown on TechnoSports.