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.

While in Los Angeles, Nikki quickly falls back into her old work routine and considers a permanent return; Chris' decision about whether or not to commit might just entice Nikki to stay in St. Louis a little while longer.

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 & 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.

Nikki feels her relationship with Chris isn't progressing the way she wants it to. When she decides to explore other options, she meets a guy who has all the traits she's looking for.

With Chris and her parents sitting next to one another at her upcoming show in Chicago, Nikki fears her act will embarrass them as she shares intimate details about her sex life on stage. First, however, they must all survive a visit to a bird sanctuary.

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.