Days after Louis Patrick Di Cerbo swiped Dr. Robin Gay Stafford into his world on the dating app Bumble in July 2020, they had a wide-ranging phone conversation that evolved into a chat about their career accomplishments.

“She was featured in Crain’s Chicago Business,” Mr. Di Cerbo, 62, said of Dr. Stafford, who is the chief dental officer for the Howard Brown Health Center, a nonprofit health care organization in Chicago that focuses on serving the L.G.B.T.Q. community.

But Mr. Di Cerbo, a lawyer, didn’t wait for Dr. Stafford, 62, to tell him that. “I immediately looked her up,” he said, laughing.

“I had to do my due diligence,” added Mr. Di Cerbo, the general counsel and chief compliance officer for Matrix Global, a Chicago-based company that provides technology and consulting services to the energy storage industry. A graduate of Hamilton College in Clinton, N.Y., he received a law degree from Boston University.

Dr. Stafford, who graduated from the University of Illinois in Urbana, Ill., and received a medical degree from Southern Illinois University in Carbondale, Ill., said she was equally impressed with Mr. Di Cerbo.

“He was very handsome and extremely intelligent,” said Dr. Stafford, who had been single for 13 years before they met. “We realized right away that we shared many passions,” she added, “such as cooking, fitness, travel, clothing, art and jazz.”

Both had been married before, too. Dr. Stafford, who divorced her first husband in 2008, described the experience as “traumatic,” adding that some of the pain it caused subsided when she “immediately connected” with Mr. Di Cerbo.

Mr. Di Cerbo had experienced pain of his own when his second wife died in May

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