Kevin spends the date pitching Sydney on an expensive travel-sales "opportunity" that she immediately recognizes as a pyramid scheme. Sydney, already miserable and still waiting for Gretchen’s promised rescue call, becomes more frustrated as Kevin drinks heavily, takes her Diet Coke, and acts as though he is doing her a favor by offering her a way out of her accounting job.

To escape the conversation, Sydney goes to the bathroom and checks her arms in the mirror after Kevin’s earlier insult. Gretchen finally calls, and Sydney vents about how awful the date has been, including Kevin’s scheme and the fact that he took a FaceTime call from his mother during dinner. Gretchen apologizes, blaming the delay on losing track of time with Randy, and offers to make it up to Sydney the next day.

When Sydney returns to the table, the check is waiting. Kevin tells her that her share is thirty-eight dollars, and although Sydney suspects the amount is inflated, she pays rather than prolong the evening. Kevin then casually assumes there will be multiple future dates and starts planning a Rocky movie marathon, while Sydney privately decides she will block him as soon as she leaves.

Outside, Kevin insists on walking Sydney home, framing it as gentlemanly behavior. Sydney reluctantly agrees but plans to misdirect him so he will not learn her actual address. She leads him through quieter residential streets and stops at a random brownstone, pretending it is her building.

At the stoop, Kevin says he had a great time and asks first for a hug, then for a kiss. Sydney refuses both and states that she has a strict no-touching policy. Kevin reacts with resentment, claims she "teased" him, and says she will never find a husband if she will not even kiss a man on a date.

As Sydney tries to leave, the situation escalates from awkward to dangerous. She considers using something from her purse as a weapon, then decides to run, but Kevin moves faster, grabs her wrist, and pins it against the brick wall. The chapter ends with Kevin physically trapping Sydney and making it clear that he does not intend to let the night end on her terms.