The initial idea for the premise of the film - two assistants attempting to set up their bosses - actually came from the film's producer Juliet Berman's real-life attempt to set up her boss with the boss of another assistant she had a crush on.
Lucy Liu was very involved in the wardrobe selection process, as she and the film's costume designer Rebecca Hofherr worked frequently together on Elementary (2012).
Harper was originally written to be 28 years old, but filmmakers changed the character's age to 25 when Zoey Deutch joined production, who was 22 at the time of filming.
During the scene at the Yankees game, the song "Power of Love" by Huey Lewis & The News plays over the stadium intercom. It was also the theme song for Back to the Future (1985) which starred Zoey Deutch's mother Lea Thompson.