This is Prudie Phones a Friend, a feature where Jenée Desmond-Harris calls a few experts for their advice to a letter writer. Submit questions to Prudence here .

Dear Prudence,

Like everyone else with taste, I’m in love with New York City and I’m visiting during the last two weeks of October. But I don’t want it to be just your run-of-the-mill itinerary.

As a diehard romantic, I want to meet someone in NYC in an incredibly spontaneous way when I visit, but I don’t know how. I’m worried I might come across as desperate or like I’m trying to force a connection. In my heart of hearts, I genuinely think I have taste; can pick up on what and how anyone is feeling; and can show a nice lady some nice chemistry, good conversation, and great company. How do I find her?

—Unabashed Year

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