Maddie receives a call from Ben who invites her to dinner on Saturday night at his place.
Maddie is internally anxious about going on a date and tries to think of excuses not to accept Ben's invitation.
Despite her hesitation and series of inventing reasons, Maddie agrees to the dinner date.
Once out of the office, Maddie looks up advice on how to prepare for a first date.
She reads an article by Lisa Fiener, which includes suggestions to distract oneself from nerves, pick a familiar location for the date, prepare conversation starters, and pay attention to body language.
Maddie also explores online forums questioning the safety and normality of a first date at a man's house.
After sharing the news of her date with her roommates Jo and Cam, they give conflicting advice about the appropriateness of going to Ben's house on a first date.
Jo insists it's a mature decision and a sign of trust, while Cam suggests it could be dangerous.
Jo helps pick out Maddie's outfit for the date, advocating for a more provocative look than what Maddie is used to.
Maddie reflects on how dating has changed since her last experience eight years prior and considers the implications of non-exclusivity after one date.
On the evening of the date, Maddie navigates her way to Ben's affluent neighborhood and debates her backstory regarding her day's activities.
Ben welcomes Maddie into his home, complimenting her appearance, and she blurts out that someone knows her whereabouts for safety.
Dinner goes well, with Ben cooking a three-course meal and both sharing personal details about their past and cooking interests.
Maddie discovers Ben's age (34) and feels uncertain about the age gap and his level of experience compared to hers.
Ben is very confident, which contrasts with Maddie's nervousness and uncertainty about how to act on a date.
Maddie gains insight into Ben's affluent lifestyle through his well-appointed house and experiences a moment of self-reflection in his luxurious bathroom.
During dessert, the two discuss their relationship histories, and Ben reassures Maddie that he is indeed single.
The date ends with Ben ordering Maddie a cab and sharing a passionate kiss with her.
Maddie returns home to her roommates, hearing Jo with a visitor and contemplates her own experiences of the evening while needing to use the toilet.