Ben Garrick, a single father still mourning the sudden loss of his wife four years prior, is pushed into a blind date by his three overprotective children, who seem to think it's their job to take care of their Dad, and his overbearing sister Mira, who's always tried to steer her little brother's life where she thought it should go. And though Ben has many misgivings, he relents and heads out for what he hopes is an easy night on the town.
His date, who's been similarly coerced, is Clementine, or Clem, as she prefers to be called, Mira's former college roommate whose life is a seeming disaster. She's estranged from most of her family, her ever-shifting career is in a state of shambles and she's fresh out of a tumultuous on-again/off-again relationship. She'd much rather be wearing pajamas and watching cringe-worthy horror flicks from the comfort of her couch, but she, too, gave in and came 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 while there are definitely sparks, they both have several obstacles they must confront before something could happen between them.
For her part, Clem must come to terms with the broken relationships littered throughout her life, and, more specifically, the unresolved feelings of abandonment from her childhood. She'll also have to contend with the sudden 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, his high school sweetheart with whom he's still quite in love, and the mixed-up emotions that come along with that. Along the way he'll need to mend the fractured familial relationships that have developed in the years since her passing, while also confronting his grief.
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.
