Sydney arrived early at a bar-restaurant for an eight o'clock dinner with Kevin, a man she met on the Cynch dating app whose photos and messages had seemed promising. When a much older, gaunt man with a messy ponytail introduced himself as Kevin, Sydney compared him against his profile and realized he looked nothing like his pictures, but she decided to give him a chance.

They took a booth, and Kevin immediately declared Sydney his "perfect woman," then qualified it by criticizing her arms as flabby. The comment rattled Sydney, making her self-conscious about her sleeveless dress, but she tried to continue the date.

When the waitress arrived, Sydney ordered a Diet Coke, adhering to her rule not to drink alcohol on first dates. Kevin pressured her to order alcohol, dismissed her choice as "not a real drink," and presumptuously ordered for both of them while signaling an apology to the waitress behind Sydney’s back.

As Sydney waited for a planned rescue call from her friend Gretchen, Kevin ogled the waitress and remarked that the waitress had "really nice arms," further insulting Sydney and cementing the mismatch between expectation and reality. The scene ended with Sydney clearly eager to end the date.