Comedian Nikki Glaser has moved back to her hometown of St. Louis, where she rekindles a relationship with her ex-boyfriend, Chris. Nikki’s mom lends a hand decorating Nikki’s bedroom with pink walls and posters of pop stars … just like any other 37-year-old woman would want.
While Nikki performs a sold-out show in St. Louis, a prank gone wrong has the police at her parent’s house looking for Nikki. Chris and Nikki go on a date, but it seems that Chris loves someone else more than Nikki.
While planning a shower for her pregnant sister, Nikki starts envisioning kids in her own future. Nikki also makes the decision to finally pursue her goal of becoming a musician and records her first single.
After finally consummating her relationship with Chris in Chicago, Nikki wants to have bigger conversations about their future, but Chris deflects. Nikki faces her singing insecurities and performs live for the first time.
Nikki feels her relationship with Chris isn’t progressing the way she wants it to, so she decides to explore other options. When she meets a guy who has all the traits she’s looking for, will she decide to call it quits with Chris?
Nikki's dislike of nature and "activities" is challenged by a visit to her parents' river cabin. Nikki and Chris go to couples’ therapy … even though they aren’t a couple.
While in Los Angeles, Nikki quickly falls back into her old work routine and considers a permanent return to the big city. Chris’ decision about whether or not to commit might just entice Nikki to stay in St. Louis a little while longer.
