Michael Earl Greene’s four children had encouraged him to make a profile on a dating app, but he’s “old fashioned,” he said. It took some convincing before he joined Bumble and made his first and last swipe ever — on Tomika Lee Anderson.

Ms. Anderson, on the other hand, was “swiping to beat the band,” she said, and “just not having any luck at all.”

Neither had many expectations when they started chatting on the app in February 2021, but a couple of FaceTime conversations led to a date that sealed their fate.

On a Saturday night that month, while Ms. Anderson, 46, was at the salon getting her hair done, he asked her out to dinner. She agreed because she already had a babysitter at home with her then 7-year-old son.

Despite being “old fashioned,” Mr. Greene, 52, is “actually pretty flashy,” Ms. Anderson said. He showed up in a Bentley, wearing a mink coat and a long platinum and diamond chain. “He reminded me of Biggie Smalls,” she added. “I was like, ‘who is this guy?’”

“It was frigid,” Mr. Greene said, but they still decided to have dinner outdoors at Tidewater Grill in Dumfries, Va., as it was the peak of the pandemic and there was no indoor seating. They stayed until the restaurant closed. In the parking lot, she told him, “I don’t know what this is going to be, but it’s going to be something.”

“The connection was instant, the conversation was effortless and he was transparent,” Ms. Anderson said. “Mike is most definitely ‘what you see is what you get.’ The only thing I didn’t see coming initially was the fur coat and the chain.”

On their third date, he asked her to be his girlfriend. And on their fifth date, he shared with her a timeline he had in mind to work their way toward marriage.

The timeline included spending time with each other’s family. They had their first vacation together in July 2021 in Ocean City, Md., with Ms. Anderson’s son from a previous relationship and Mr. Greene’s two sons from his first marriage. (He also has two daughters from that marriage, but they were unable to join. Additionally, he had a second marriage that ended in divorce.)

Mr. Greene drove 360 miles a week to see Ms. Anderson. She lives in Woodbridge, Va., and he in the Baltimore area, which is around 60 miles away. Mr. Greene, who graduated the U.S. Naval Academy with a bachelor’s degree in mathematics, is the owner of Platinum Plus Limousines, a luxury car service company. Ms. Anderson, who has a bachelor’s degree in political science from the University of Virginia, owns three businesses: Motivated Mamas, Single Parents Who Travel and Manifest Greatness Media.

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During the holidays that year, he bought her a diamond ring and decided he would propose on New Year’s Eve. But after a huge upset in a game of Monopoly, he decided to wait until the next day to propose.

“I had whooped his butt in Monopoly so bad, he was not feeling giving me the ring then and there,” she said.

“I was hurt,” he added.

But things went awry the following day, as well. He proposed to her on Jan. 1, 2022, while she was coming out of the shower with her hair “half wet, half dry,” she said. He pulled the ring out of a velvet bag rather than a box because there was an inventory shortage at the time.

“I was looking at him like, ‘Are you serious? This is how you want to propose?,’” she said.

“She was about to beat me up,” he added.

Additionally, when she tried to take the ring off the following day, it would not budge — “not with butter, not with soap, nothing,” she said. They ultimately went to the fire department, and a firefighter clipped it off.

After a disappointing proposal, and a broken ring (they were able to salvage the diamond), she asked him for a “do-over,” she said, which took place on Feb. 14, 2022.

The do-over was “flawless,” Ms. Anderson said.

Together, they chose a new band for the diamond, and Mr. Greene arranged for a makeup artist, a limousine, a red carpet and a private suite decorated with roses at La Vie in Washington, Ms. Anderson’s favorite restaurant.

On March 4, the couple were wed at Beaches Turks & Caicos. Ms. Anderson was inspired by a wedding she attended on the island 20 years ago. “I took a mental screenshot and said, ‘If I ever got married, I would want to get married there.’” Sherlock Padmore of Christ is the Answer Church officiated in front of 30 guests. They jumped the broom at the ceremony, and Ms. Anderson’s son, now 9, was the ring bearer.

The couple did not hold back during their wedding weekend — they hosted three days filled with events, including a welcome reception, game night and a pool party. Mr. Greene was so full of joy on the morning of the wedding that he sang to her “Let’s Get Married” by Jagged Edge, even though he’s “terrible at singing,” he said.

“Mike is the first man who really reminds me of my father, who is my absolute hero,” Ms. Anderson said. “Honestly, I felt like there were times where I was very close to giving up on finding my partner. It’s a cliché, but really, truly, it never is too late.”