“Tell me what you’re thinking?”

For as long as she can remember, Katie Rappaport has enjoyed asking that question whenever she noticed that a family member or friend had drifted into deep thought.

“It’s a great conversation starter, just ask James,” said Ms. Rappaport, 33, a creative director in New York for Condé Nast.

She was referring to James Strickland, also 33, and their “unforgettable conversation,” as she put it, that took place in October 2018 in Mr. Strickland’s Nashville apartment.

Three months earlier, they began dating in New York after matching on two apps, Hinge and the League. At the time, Mr. Strickland was busy with an internship at an investment banking firm in New York that was a part of his studies at Vanderbilt, where he was a year away from earning an M.B.A.

When Mr. Strickland returned to Nashville, he sent Ms. Rappaport four enormous balloons, together spelling XOXO, as well as 50 additional balloons to her office in Lower Manhattan, as a way of demonstrating just how much he missed her.

Ms. Rappaport was soon heading to Nashville, sitting with Mr. Strickland on his sofa. They talked about religion — she’s Jewish, he’s Roman Catholic — and their mutual love of the outdoors, where both enjoy fly-fishing. And they discussed their love affair with New York City. She grew up in Indianapolis and worked with disadvantaged youth in rural Ohio through AmeriCorps and later at Ohio State University, and he lived in Tallahassee, Fla., and in several other areas of the state before arriving in New York by way of Nashville.

At some point during their long chat, Ms. Rappaport noticed that Mr. Strickland had drifted into deep thought, and instinctively, she sprung into action. “Tell me what you’re thinking,” she said.

He did not mince words, creating the kind of conversation starter that neither could have possibly imagined at that point of their brief relationship. “I have been thinking about what it would be like to marry you,” he told Ms. Rappaport. She could only stare back in stunned disbelief and say, “Are you asking me to marry you?”

He told her he was, but just not at that time in their lives.

“Ask me again,” she said.

He obliged, and they both agreed to let that precious moment serve as a verbal commitment to one another and that one day, they would indeed get married.

On June 21, 2019, Mr. Strickland got down on one knee and proposed to Ms. Rappaport at Hotel du Cap-Eden-Roc in Antibes, France.

They spent the next two days in Beaulieu-sur-Mer on the French Riviera, drinking champagne and celebrating.

The couple initially chose to be married June 6, 2020 at Newfields, a 152-acre campus that houses the Indianapolis Museum of Art. They had already sent out invitations for 250 guests. But because of restrictions created by the coronavirus, the couple, who were able to save the date, moved their wedding ceremony and reception to the home of the bride’s parents in Indianapolis.

Rabbi Brett Krichiver officiated before the couple and 16 members of their families.

Shortly after they were married, the newlyweds went outside and rode bicycles, and were saluted by neighbors, some hoisting glasses of wine, others tossing flower petals in their direction.

When asked what she was thinking while bike riding in her wedding dress, the groom pedaling beside, the bride said, ‘‘I was thinking that I could not have imagined a sweeter ending to our wedding day.”