His date, who's been similarly coerced, is Clementine, or Clem, as she prefers to be called. And while she'd much rather be wearing pajamas and watching cringe-worthy horror flicks from the comfort of her couch, she, too, goes out looking for a laid-back evening full of cheap drinks and so-bad-it's-good music that she could leave behind at the end.
What neither of them expected was to meet someone and feel something. And though there are definitely sparks, they must first deal with the broken relationships littered throughout their lives.
Clem must come to terms with her unresolved feelings of abandonment, while also contending with the re-appearance of her kind-of ex, Rory, whom she still has deep feelings for, and figure out how to move on from the toxic relationship they shared that both haunts and comforts her.
Ben, on the other hand, must deal with the harsh realities of life without his wife, whom he's still quite in love with, and the mixed-up emotions that come with that. While confronting his grief, he'll also need to mend the fractured family relationships that have developed in the years since her passing.
Ben and Clem make their way through Chicago's prominent nightlife, sharing an evening (and early morning) of loud music, sarcasm, laughter, pain, intrusive Uber drivers, and cross-dressing karaoke, all while trying to make sense of the burgeoning love that neither of them anticipated."