A story of two overworked and underpaid assistants, Harper and Charlie (Deutch and Powell), who are wasting their 20s working for superiors who treat them like dirt and work them 'round the clock.

Harper and Charlie commiserate with each other about their crazy bosses (Liu and Diggs) and realize that they would have much more free time if the people they worked for weren't single.

They concoct a plan to solve their problem by setting up their respective bosses with each other. As assistants they have all the access and all the power to pull the strings behind the scenes to lure their unwitting bosses into a faux romance.

When the plan is a huge success, Harper and Charlie are now free to live their lives. But, things start to spin out of control as they begin to discover what started out as a harmless plan could lead to some unanticipated consequences.