In 2011, Jess is a senior at an Ivy League college. She drinks far too much, she dates the wrong men and spends her days adopting the values of her privileged friends whilst painfully aware that she isn't like them - all too often the only Black woman in the room. Jess craves belonging and acceptance, but she's fed up with the casual racism, the class debates about affirmative action, and she's particularly fed up with one know-it-all, Josh, who isn't shy about broadcasting his infuriating and insensitive opinions.

The years turn and Jess and Josh move in and out of each other's lives, working at the same investment bank, and slowly, tentatively forming a mismatched friendship. He is sure of his place in the world, she is just beginning to discover hers - but the momentum of being young and, soon, in love propels their relationship forward. That is, until 2016. Trump is approaching office and the cultural landscape is shifting. Jess is forced to finally ask whether they are meant to be, and if, in fact, everything's fine.