On the brink of losing her childhood home, Maddie discovers an intriguing job listing: wealthy helicopter parents looking for someone to “date” their introverted 19-year-old son, Percy, before he leaves for college. To her surprise, Maddie soon discovers the awkward Percy is no sure thing. However, he proves to be more of a challenge than she expected, and time is running out before she loses it all. A bartender who's down on her luck takes on an unusual challenge when a wealthy couple hires her to romance their socially awkward son.