She Expressed Doubts. He Proved Them Wrong.

The surprise May 25 wedding De-Shazo Wilkinson put together for his fiancée, Jacarra Wilson, was brought on by an emotional gut punch.

After postponing their wedding for a second time in late March because of the coronavirus — the first, last fall, was caused by the shutdown of the venue they had chosen in Orlando, Fla. — Ms. Wilson had said the unthinkable. “She was like, ‘This is strike two. What if it just wasn’t meant to be?’” said Mr. Wilkinson, 32, an assistant principal at KIPP Impact Middle School in Jacksonville, Fla. “My heart sank. I knew I had to figure out something.”

Ms. Wilson, 29, and Mr. Wilkinson met as students at the University of Central Florida in Orlando in 2007. Both were trying out for Rukus, a hip-hop dance team, and both made it. They began dating. By January 2010, a few months before Mr. Wilkinson graduated, they had gotten serious. But then Mr. Wilkinson landed a teaching job in Lake City, Fla., while Ms. Wilson had three years to go before finishing her degree.

In 2014, when he moved to Jacksonville for another teaching job, Ms. Wilson was busy establishing herself as a hair and makeup artist in the Orlando area. Long-distance dating was by then familiar. But three years later, enough was enough. “It’s about 162 miles between Orlando and Jacksonville,” Ms. Wilson said. “Finally I said to myself, What are we doing? I can do hair and makeup anywhere.” She and Mr. Wilkinson moved into a new apartment together in Jacksonville in 2018. On Jan. 30, 2019, he proposed.

“It was the nine-year anniversary of when I asked her to be my girlfriend,” Mr. Wilkinson said. He had arranged nine dozen roses around their home and gotten down on one knee. Ms. Wilson, who had been complaining minutes earlier that she thought a proposal might never come, was shocked. “I was like, Are you kidding me?” she said. Her yes was followed by a flurry of wedding planning.

After their first two wedding plans fell through, Ms. Wilson was devastated and began expressing concerns about their marriage being not meant to be.

That’s when Mr. Wilkinson sprung into action. With the help of their wedding planner, Michelle Harbridge of the Wedding Authority, he confirmed that the Treasury on the Plaza in St. Augustine, Fla., their second venue, would still welcome them on May 25, though without their guests. He asked their parents and a few other family members to go to St. Augustine with them that Memorial Day, to commemorate what would have been their wedding day.

“We had on our cheesy fiancé T-shirts — his said, ‘I stole her heart,’ and mine said, ‘So I stole his last name,’” Ms. Wilson said. But she had also packed a white outfit she bought to cheer herself up, because Mr. Wilkinson told her to plan on a family photo shoot while there.

When they arrived at the Treasury, Mr. Wilkinson was ready. “In front of our parents and everybody I said, ‘Will you marry me right now?’” He was again on one knee.

“I was sobbing like an idiot,” Ms. Wilson said. An hour later, after 100 cardboard cutout faces of guests who couldn’t be with them were arranged on chairs around the venue, and after Ms. Wilson’s makeup was partially done — “I only had eye shadow on one eye,” she said — they were married over Zoom by Dwayne Jones, a military chaplain stationed in Korea who had been Mr. Wilkinson’s childhood pastor and who is ordained in Florida.

By then, Ms. Wilson had come around to the idea that their marriage was meant to be.

“I came out of it having so much respect for him, because he heard my concerns and he met them with something more than I could have ever imagined,” she said. “I was infinitely satisfied.”