Sydney hides in the coffee shop bathroom after her severe nosebleed, embarrassed by the blood on her pale pink blouse and worried she looks alarming. Tom returns with a replacement shirt, jokingly handing her an “I Love New York” T-shirt. Although Sydney hates the touristy look, she changes into it because it is better than staying covered in blood, and Tom even offers to carry her ruined blouse in his jacket pocket.

As they walk to an Indian restaurant, Tom stays attentive and easygoing, which makes Sydney compare him favorably to past bad dates. When Sydney explains that the nosebleed was caused by von Willebrand’s disease, Tom immediately recognizes the condition and shows off his medical knowledge. His competence and kindness impress Sydney, even as she keeps searching for flaws because he seems almost too perfect.

At the restaurant, Tom continues to be polite and considerate, holding doors and pulling out Sydney’s chair. Sydney asks about his family, and Tom reveals that his father died of a heart attack when Tom was in high school, leaving him and his mother alone together. The conversation then turns to work: Tom says he is a pathologist at NYU, and Sydney learns that he is specifically a medical examiner who mostly performs autopsies, a detail that unsettles but also fascinates her.

Once the conversation shifts away from work, the date becomes warmer and more flirtatious. Sydney tells Tom she is an accountant, and they joke easily while ordering dinner. Tom admits he wanted Sydney’s number when they first met but held back because she had just been attacked and because he was ending another relationship. When Sydney blurts out that she wants to get married someday, Tom responds by toasting “someday,” and Sydney leaves the moment feeling that Tom might genuinely be a serious romantic possibility.