After exchanging a few pleasantries, Katherine Roberts Maher and Ashutosh Upreti got down to business over drinks in April 2019 at the now-shuttered Bond Bar in San Francisco’s Mission District.
“I thought he was more interested in being my general counsel than my date,” Ms. Maher, 40, said. At the time, she was the chief executive at Wikimedia Foundation, the nonprofit organization that operates Wikipedia, where she stayed until 2021.
So one question followed another.
“How do you think about organizational risk, and what does a strategic legal function look like?” asked Ms. Maher, who graduated magna cum laude with a bachelor’s degree in Middle Eastern and Islamic studies from N.Y.U. She is the chair of the board of directors at Signal Foundation, the nonprofit behind the secure messaging app, and is a nonresident senior fellow for democracy and technology at the Atlantic Council, a nonpartisan research center.
Mr. Upreti, who is 42 and a lawyer, politely played along for about an hour. “Do you ask all your dates these questions?” he finally asked. As far as he was concerned, he was staying put as the legal director for autonomous vehicles at Lyft, the ride-share company. He is now the chief legal officer at CareRev, a technology company that focuses on health care staffing.
Mr. Upreti received a bachelor’s in electrical and electronic engineering from the University of Auckland in New Zealand, graduating with first class honors, and then backpacked solo through 26 countries. Afterward, he received a law degree and graduated with honors from George Washington University.
After clearing the air, they had a good laugh and another drink. Later, they even shared a kiss and stopped for burritos at Pancho Villa Taqueria nearby.
“I thought he was really sweet,” Ms. Maher said. She had met him a couple of days earlier at a mutual friend’s nondenominational Seder at Manny’s, a community and civic event space in the Mission District. All of the 100 guests there shared where they and their grandparents were from, and told stories about freedom or a lack of it.
Mr. Upreti and Ms. Maher found each other’s stories intriguing: He spoke of his aunt, who, as a schoolgirl during colonial rule in India, briefly stepped foot on a road designated only for the British. Ms. Maher talked about two friends, both Arab activists, who were recently imprisoned and tortured in Syria and Egypt.
“All of a sudden, the whole world was in the room,” Ms. Maher said. Her parents, who were visiting from her hometown, Wilton, Conn., and one of her younger brothers, who also lived in San Francisco, were in attendance. Later, Mr. Upreti introduced himself to her and her family, and they ended up chatting.
“I noticed Katherine and her family,” said Mr. Upreti, who was born in Bryan, Texas, and raised in New Zealand. “They had a great vibe.”
More dates followed after their “first” one: They listened to music at the Black Cat jazz club and then saw “Hamilton” at the Orpheum Theater, both in San Francisco.
“Let’s make this exclusive for a month,” Mr. Upreti said. Ms. Maher was impressed by his intentionality. “There’s something good here,” he said. “If it isn’t true, we don’t waste each other’s time.”
Ms. Maher — who traveled 180 to 200 days a year, mainly for work — wanted that, too, but “it absolutely scared me,” she said. At the time, she was getting over a recent breakup. “I kept calling him a good egg: He was kind. He was funny. He was thoughtful,” she said.
As they spent more time together, she began using the washer and dryer at his apartment regularly, and they watched “Game of Thrones” on his television every Sunday — she had neither in her jewel-box studio apartment in the Mission Dolores neighborhood. “I like to say she was only dating me for my appliances,” Mr. Upreti joked.
On March 1, 2020, they got an apartment together around the corner from her old studio, and a week later, the Covid-19 pandemic hit.
“The pandemic amplified our relationship,” Mr. Upreti said. When her father’s health declined, Mr. Upreti traveled to Connecticut with her in mid-July. For the next three months, they stayed with her mother, and her father died on Oct. 5, 2020.
Ms. Maher’s mother and her two labradoodles stayed with the couple in San Francisco until vaccines became available in March 2021. The couple traveled around the world in early 2022 and moved to New York that June.
On March 23 — atop Twin Peaks and overlooking the Golden Gate Bridge, the Pacific Ocean and San Francisco Bay — Mr. Upreti proposed out of the blue. “We should get married,” he said.
“What?” Ms. Maher said over the sound of the wind. “I can’t hear you.” She then hugged him without saying yes right away.
He told her to take her time — “a day, a week, a month.” Five weeks later, she said yes, and soon after, they adopted an Alaskan malamute mix.
On July 22, Erica Kochi, a friend of the couple who became a one-day deputy marriage commissioner in San Francisco, officiated the wedding before 140 guests on the lawn of Willow Camp in Stinson Beach, Calif. The day before, the groom rode in on a white horse for a Hindu ceremony.
“It was two days of cross-cultural celebration and community,” Ms. Maher said, “and a really big dance party.”