Sydney arrives punctually at a restaurant for an eight o clock dinner date with a man named Kevin, whom she met through the dating application Cynch. Their meeting was originally scheduled for six o clock just for a drink, which Sydney preferred as an easy exit strategy, but Kevin had messaged her to postpone and turn it into a dinner. Despite some initial hesitation, Sydney agreed because their previous online conversations were pleasant and his profile photographs depicted a charmingly youthful man resembling a young Matt Damon. Upon arriving at the bar, Sydney is approached by a man who introduces himself as Kevin, but she is immediately shocked by his actual physical appearance. The man standing before her looks at least ten years older than his profile picture, appears gaunt, and has a receding hairline with a scruffy blonde ponytail. Checking her phone covertly, Sydney confirms that he looks nothing like his profile picture.
Despite her disappointment, Sydney decides not to leave immediately, reminding herself that their text exchanges were good and noting that she has arranged a safety plan with her friend Gretchen, who is set to call her twenty minutes into the date with a fake emergency. Sydney and Kevin walk to a corner booth, where she notes that he is tall but uncomfortably thin like a broomstick. Kevin praises her appearance, stating that she looks exactly like her photo and calling her his ideal woman. Sydney feels flattered by the compliment and starts to feel a slight attraction toward him despite his misleading profile picture. However, Kevin abruptly ruins the pleasant mood by criticizing her body, telling her that her arms are flabby and causing Sydney to feel instant regret over choosing a sleeveless dress.
The situation worsens when a waitress comes to take their drink order. Sydney requests a Diet Coke, explaining her personal rule against drinking alcohol on a first date with a stranger to keep her mind clear. Kevin rudely mocks her choice in front of the waitress, insisting that a Diet Coke is not a real drink, before rolling his eyes and ordering a beer for himself while winking apologetically at the waitress. Sydney feels growing frustration and checks her bag for her phone, hoping Gretchen will call soon. Although thirty four year old Sydney tries to rationalize giving him a few more minutes to avoid endlessly repeating first dates, Kevin completely destroys any remaining goodwill when he watches the waitress leave and openly admires the waitress for having beautiful arms. Sydney is left desperately waiting for Gretchen to call and rescue her from the awful date.