When Zachary Ian Miller first met Jill Diane Rafson, he faced a tough question as a football fan: playoff game or second date?

It was January 2022, and Mr. Miller and Ms. Rafson had matched on the dating app Hinge. After about a week of chatting on the app — subjects included pop culture and “zoodles,” or zucchini noodles — they met for their first date at the bar Stout NYC, on 39th Street in Midtown Manhattan.

At the time, Ms. Rafson, 42, was in the process of interviewing for a new job after spending nearly 17 years at Roundabout Theatre Company, one of the largest nonprofit theaters in the United States. There, she was the associate artistic director and a founder of the Roundabout Underground program, which helped kick-start the careers of playwrights like Steven Levenson, who won a Tony Award for “Dear Evan Hansen.”

Over the years, she had been more focused on her career and used dating apps on and off. But in 2022, as the world reopened after pandemic lockdowns, her mind-set shifted and she decided to prioritize her personal life.

Mr. Miller, 38, who goes by Zach, caught her eye because his Hinge profile revealed a sense of humor. In one photo, he was drinking a “Yoda-tini,” a green cocktail in a martini glass decorated to look like Yoda from “Star Wars.” Ms. Rafson was charmed.

At the bar, their conversation flowed easily. Although Ms. Rafson had told virtually no one that she was interviewing for a job at Classic Stage Company, an Off Broadway theater company, she found herself telling Mr. Miller.