Can two overworked assistants manipulate their bosses into love to reclaim their own lives?

Entertainment · Published 3 October 2026 · Updated 25 October 2026 Swipe more like this →

In short: In the 2018 romantic comedy Set It Up, two exhausted New York City assistants hatch a scheme to pair their demanding bosses together. By orchestrating dates and forced encounters, they hope to secure some personal freedom, but their meddling quickly spirals into a series of complicated, unintended consequences.

Directed by Claire Scanlon and written by Katie Silberman, the film centers on Harper Moore and Charlie Young. Harper serves as the assistant to Kirsten Stevens, a former journalist running a sports media empire, while Charlie works for the abrasive venture capitalist Rick Otis. Meeting by chance over a dinner delivery mishap, the two realize they share a common burden: their bosses' relentless demands leave them with no time for their own lives. Harper jokingly proposes that if Kirsten and Rick were dating, they would be too distracted to overwork their staff.

The assistants begin their matchmaking mission with a failed attempt to trap their bosses in a stalled elevator, aided by a janitor named Creepy Tim. They eventually succeed by manipulating a kiss-cam operator at a baseball game. As the bosses begin dating, Harper and Charlie find the relief they craved, but the ruse requires constant maintenance. They must secretly organize vacations and gifts to keep the relationship afloat, even as Charlie’s own relationship with his girlfriend, Suze, suffers from his lack of availability.

The plan unravels when Charlie discovers that Rick is only dating Kirsten to spite his ex-wife, Kiki. When Harper learns the truth and realizes Charlie kept it from her, she exposes the manipulation to Kirsten, leading to her firing. However, the chaos ultimately forces both assistants to reevaluate their paths. Charlie quits his job to pursue his own interests, and Harper chooses to focus on her writing career rather than returning to her old role. The film, which holds a 92% approval rating on Rotten Tomatoes, concludes with a nod to the classic rom-com formula, proving that even the most calculated schemes can lead to genuine, unexpected connections.

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