“Dating in New York can be so jading and demoralizing,” said Allegra Teresa Hanlon.

If films and television shows are any indication, it seems to have been that way for some time. It was the subject of Carrie Bradshaw’s musings in HBO’s “Sex and the City.” It was also reinforced in the 1989 romantic comedy “When Harry Met Sally,” when Marie (Carrie Fisher) proclaims to Jess (Bruno Kirby), while snuggled in bed, “Tell me I’ll never have to be out there again” — “out there” referring to the fraught world of New York dating.

For Ms. Hanlon and Thomas James Fitzpatrick, the complexities of the New York dating scene became a point of connection during their first date at Jackson’s Eatery in Long Island City, Queens, in June 2019.

“I’m so tired of dating in New York,” he told her while shaking his head.

Mr. Fitzpatrick had been living in Queens for three years. Ms. Hanlon was in New York for just a year, but that was enough for her to feel exhausted by the cycle of meeting new people, conversations fizzling out or ghosting. And, as Mr. Fitzpatrick put it, the air of, “You’re pretty good, but you’re not perfect, so I’m going to find someone else.”

He added: “It just felt so fast and transactional, and, I don’t know — it just felt not that romantic.”

Four years after their first date, Ms. Hanlon was able to place her arm around Mr. Fitzpatrick and recite the same phrase from “When Harry Met Sally,” her favorite movie, re-enacting the scene on the night of their engagement.