Christopher Michael Kirchhoff let his experience working with high-level military officials guide him when he started online dating in 2019.

“I approached it sort of like military planning,” said Dr. Kirchhoff, who was a director for strategic planning at the National Security Council during the Obama administration and holds a Ph.D. in social and political sciences from the University of Cambridge. “Assume the worst and hope for the best.”

Often, this approach meant employing some low-level strategic ops before going on first dates, including the one that Dr. Kirchhoff arranged that March with John Chia-An Tsou, whom he met on the app Hinge. Once the two matched, “of course I immediately Googled John,” Dr. Kirchhoff said. “Opposition research is very important.”

But Dr. Kirchhoff, 43, found little to oppose in Mr. Tsou’s background. In fact, he and Mr. Tsou, 42, had traveled paths so similar he thought, “How do I not know you already?”

Both were raised in Ohio and attended Harvard University as undergraduates — Dr. Kirchhoff in the class of 2001 and Mr. Tsou in 2002. Later, each lived at the same time in the United Kingdom, Washington and San Francisco, where they started dating and still live.

Mr. Tsou was also aware of their overlapping pasts by the time of their first date for coffee at Dr. Kirchhoff’s apartment in the Mission District. But that didn’t dispel his concerns about their compatibility.

“Chris’s place was covered with books,” he said. The tomes, heavy on titles about war and conflict, gave him pause. “There was a little bit of ‘Oh, I don’t know if I’m academic enough for this guy.’”

After hours of chatting, though, both sensed a definite chemistry. Dr. Kirchhoff said goodbye wondering, as he put it, “if this is ‘the one.’” A second date came in less than a week.

When he met Mr. Tsou, Dr. Kirchhoff was legally separated from his first husband; their divorce became finalized in 2020 after seven years of marriage. The process had soured him on the prospect of remarrying, but meeting Mr. Tsou caused him to re-evaluate that position within months.

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In July 2019, while the two were on a road trip through Northern California, they broached the subject of a future together after stopping for dinner at Fern Bar in Sebastopol. “It all kind of came out during that one meal,” Mr. Tsou said. Before leaving the restaurant, each had said they wanted to marry the other.

The following year, just before the start of the pandemic, Dr. Kirchhoff made five trips to Lowe’s for boxes strong enough to carry all his books and tipped a moving company generously to move him into Mr. Tsou’s condo in the Japantown neighborhood of San Francisco.

Dr. Kirchhoff, who after leaving the White House helped to start Schmidt Futures, a philanthropic organization founded by the former Google chief executive Eric Schmidt, is now a senior adviser to the Special Competitive Studies Project, a group founded by Mr. Schmidt and former Secretary of State Henry Kissinger that advocates policies focused on long-term U.S. competitiveness in technology. Mr. Tsou is the vice president for marketing at the reservation platform OpenTable.

Both said that living and working from home together during the pandemic helped to deepen their relationship.

“Hearing him on conference calls with his team, with his kindness and care for people coming across so clearly, I fell in love with him all over again,” Dr. Kirchhoff said.

Mr. Tsou fell further for Dr. Kirchhoff watching him display many of the same qualities. “There’s a really strong kindness there with Chris,” he said. “Despite all the achievement, he’s always thinking about others.”

On a return trip to Fern Bar in October, Dr. Kirchhoff proposed to Mr. Tsou. They were married July 9 at Low Camp at Kualoa Ranch, in Kaneohe, Hawaii. Their friend Hunter Keith, a licensed officiant with the Hawaii Department of Health, who was ordained by the Church of the Latter-Day Dude for the occasion, officiated.

Among the 110 guests were the science and technology scholar Sheila Jasanoff, Dr. Kirchhoff’s college adviser and mentor, and the theoretical cosmologist Chanda Prescod-Weinstein, Mr. Tsou’s college roommate. Both gave readings at the ceremony.

Afterward, the couple swapped their dress shoes for sneakers with rainbow laces and cut a wedding cake with rainbow layers. Reflecting on their union, Dr. Kirchhoff said he was grateful to end up “in the arms of a man as magnificent as John.”