In November 2020, Andrew Quintero rented Blu Mar, a seafood restaurant in the Hamptons, to host a large dinner party in hopes that Sophia Farah Babai would attend. That night he watched Ms. Babai’s friends walk in, but she wasn’t among them. Again.

“I was always hoping that she would show,” Mr. Quintero said.

Mr. Quintero first noticed Ms. Babai in a mutual friend’s Instagram story in 2016, when he was a freshman at Quinnipiac University and she was a freshman at the State University of New York at Albany. He asked that friend, Janice Murphy, for an introduction, but it would take four years for that moment to come.

So Mr. Quintero, who became affectionately known as “Gatsby” among Ms. Babai’s friends, began hosting lavish gatherings in hopes of meeting her, as the titular character of F. Scott Fitzgerald’s “The Great Gatsby” does as part of his campaign to impress the wealthy socialite, Daisy Buchanan.

There were suite boxes for basketball games at Barclays Center in Brooklyn, dinners and concerts to which he would casually ask mutual friends to bring Ms. Babai — to no avail.

Finally, in early 2020, Ms. Murphy, the mutual friend who posted the 2016 Instagram story, planned drinks at Tao Downtown in Manhattan. Mr. Quintero had no plans to make the hourlong drive from Long Island, where he lived, to join. But when he learned Ms. Babai would be there, he got in his car.