Sydney arrives early for a Cynch date with Kevin after reluctantly agreeing to move their plans from drinks to a later dinner. She had felt cautiously hopeful because Kevin seemed kind in their messages and looked attractive in his profile photos, so she waits at the bar expecting a promising first meeting.

When a stranger approaches and introduces himself as Kevin, Sydney is shocked because he looks nothing like the man in the app photos. She compares his face to the profile on her phone and sees obvious differences in age, build, hair, and overall appearance. Even so, Sydney decides not to walk out immediately because she feels judging him only on his looks would be shallow, and she knows her friend Gretchen is scheduled to call soon with a rescue excuse if needed.

Sydney and Kevin take a booth, and Kevin quickly makes Sydney uneasy. He first flatters Sydney extravagantly by calling her his perfect woman, which briefly makes her feel better about staying. But Kevin immediately undercuts the compliment by criticizing Sydney's supposedly flabby arms, causing her to become self-conscious and regret wearing a sleeveless dress.

When a waitress comes over, Sydney orders a Diet Coke because she avoids alcohol on first dates with men she met online and wants to keep her judgment clear. Kevin challenges her choice, dismisses it as boring, and then orders for both of them in a patronizing way. His behavior reinforces Sydney's discomfort and makes her more eager for Gretchen's planned interruption.

Any remaining hope for the date collapses when Kevin openly ogles the waitress and praises her arms right in front of Sydney. By the end of the chapter, Sydney is trapped in an increasingly awkward and disrespectful date, and Gretchen's rescue call feels urgently necessary.