A week after Wesley Drew Wheeler was laid off from his job writing catalog copy at the music company BMG a woman he had hoped to connect with on the dating site Lavalife sent him a wink. The layoff, announced on Halloween 2007, felt like an unusually unkind trick. “I’m trying to go out with her, and now I’m unemployed,” he said. “What a catch, right?”

To Renee Blady, sender of the wink, his job status didn’t matter. As an executive recruiter with LHH Recruitment Solutions, then known as Parker + Lynch, “I deal with unemployed people all the time,” she said. A note Mr. Wheeler, who goes by Drew, had written her on the site had her convinced he was much more than his résumé.

“He wrote something like, ‘When you gave me a like it was like when you’re at a dance and your eyes meet across the dance floor,’” she said. “It was the most amazing message I had gotten from anyone.”

Mr. Wheeler, 63, and Ms. Blady, 65, were both living in Brooklyn then — Ms. Blady in Park Slope and Mr. Wheeler in Carroll Gardens. Both were newly navigating New York’s singles scene after first marriages that didn’t last. Ms. Blady was divorced in 2007. Mr. Wheeler, who has a daughter, was in the process of a divorce that would be finalized in 2012.

Their first date, on Nov. 11, was at the 12th Street Bar & Grill in Park Slope, which has since closed. A drink turned into dinner there. “We talked about music,” Mr. Wheeler said. For him, there may be no more captivating subject.

Now a freelance copy editor for publishers like Pegasus Books, Mr. Wheeler has written five books on rock acts from Metallica to Cyndi Lauper under the pseudonym Chris Crocker. In the mid-1980s, he worked as Frank Zappa’s publicist.

Ms. Blady is a self-described Deadhead. “We both liked jammy kinds of bands,” she said. “We had a lot of music in common.” The date ended with what she called a “head bump.”

“It was like a nuzzle,” she said. “It was so sweet.”

By the end of 2007, Mr. Wheeler had asked her to be his girlfriend. In 2013, when his landlady died, he moved into her place in Park Slope. Seven years later, at the start of the pandemic, they left the city for good and moved to a house Ms. Blady owns in Craryville, N.Y.

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Marriage had seemed like a good idea to both for years. But Mr. Wheeler demurred, partly for reasons related to his daughter’s financial aid package for graduate school.Even after her graduation, engagement “was a nudge situation.”

Once nudged, though, he got creative. Back in 2007, when they first started dating, Ms. Blady sent Mr. Wheeler the lyrics to one of her favorite songs, “Better Things.”

“He was a little bit down about losing his job at the time, and I told him, this song always makes me feel good and hopeful,” she said. “Better Things” was written and originally recorded by the Kinks, but the version Ms. Blady knew and loved was by the singer and songwriter Dar Williams. Mr. Wheeler knew a publicist for Ms. Williams, Cary Baker.

Through Mr. Baker, he arranged for a private Zoom concert on Oct. 11, 2021, fibbing to Ms. Blady that Ms. Williams was putting on a live show online. The first and only song she sang was “Better Things.” Toward the end, she looked into her computer camera and said the song had been a dedication. Then she added, “And now I think Drew has something he wants to ask you,” Mr. Wheeler said.

Ms. Blady, who had figured out what was happening when she noticed they were the only two on the Zoom, was in tears. Mr. Wheeler leaned in and asked her to marry him.

“I screamed before he had a chance to get the words out,” Ms. Blady said. “And then I said yes again.”

On Nov. 20, they were married at Copake Country Club in Craryville. Ms. Blady’s nephew, Jordan Blady, ordained by the Universal Life Church for the occasion, officiated before 94 mostly vaccinated guests. Ms. Williams was not among them, but not because they didn’t want her there. For the engagement, “Dar was so lovely and wonderful to us,” Mr. Wheeler said. “She never even accepted payment.”

“We just didn’t want to bug her,” he said.