When Dolly returns home with a new haircut and clothes, Gus and Christopher are unimpressed. Dolly takes Gus for ice cream and explains her business arrangement with Stewart Whitfield: She will pretend to be his girlfriend for a few events, and in return, he will pay for the new roof on their father’s house. Gus finds the situation “crazy” but understands, comparing it to pretending to be a professional baseball player for a while.

Stewart picks Dolly up for a cancer fundraiser in Providence where he is being honored. Feeling insecure, Dolly asks for a compliment, which Stewart awkwardly provides after explaining he avoids complimenting employees for legal reasons. At the event, Dolly fumbles their cover story about meeting on bikes; Stewart supplies the park name (Boston Common), and the woman who asked which park they met at points out that cycling is forbidden there. In the restroom, she uses her personal sewing kit to fix a broken dress strap for Jennifer Quigley, the head of the charity. During his speech, Stewart reveals that Busy is a childhood cancer survivor. Afterward, to maintain their ruse, he leans in close to Dolly. She notices that he “sniffs” her and makes a joke, but she feels an attraction between them.