Harper (Zoey Deutch) is an assistant to Kirsten (Lucy Liu), a famous and fearsome ESPN reporter. Harper wants to be a writer but can't muster the nerve to follow through on her one good idea; on top of that, her days are so long than whenever she does try to write, she's so tired that "everything I write is, like, bad." Charlie (Glen Powell) is an assistant to Rick (Taye Diggs), a Tom Wolfe Master-of-the-Universe type whose job never quite comes into focus but definitely involves huge sums of money.
The bosses' employers are located in the same building, which allows Charlie and Harper to meet cute in the lobby one late night. Harper orders food for her boss without realizing the restaurant is cash-only. Charlie, who just missed the cutoff to order his boss' favorite steak, spots an opportunity to redeem himself, pays for the order, and claims the whole thing; this leads to a charming negotiation that splits up the food, and ultimately to a shared realization that if they can trick their Type A bosses into falling in love, they might get their lives back. "It's hard to bark orders at someone when your tongue is down someone's throat," Harper says.
Harper just signed up for Tinder and is going out on lots of dates, and Charlie is devoted to a gorgeous but materialistic girlfriend (Joan Smalls) who doesn't appreciate him. But the two spend so much time together plotting their bosses' romance that they become close friends, and there are moments where they click so well that you can sense them laboring to deny the obvious. Director Claire Scanlon and screenwriter Katie Silberman are able to imagine these two as both credible human beings and classic romantic comedy types (Charlie is young Jack Lemmon poured into a tall preppy frame, while Deutch can remind you of either Ellen Page or Diane Keaton, depending on the scene and how fast she's talking).
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