Erin Courtney Bellsey has always loved playing matchmaker. By her count, she has paired dozens of couples, two of which are now engaged.
In October 2019, a friend flipped the script on Ms. Bellsey, asking if she’d be interested in being set up. Around that time, Charles Mellon Leonard was asked the same question by his older brother, who was in cahoots with Ms. Bellsey’s friend.
Mr. Leonard and Ms. Bellsey, who had each just ended long-term relationships, agreed to meet for a date. Later that month, they got together at the Alembic, a bar in the Haight Ashbury neighborhood of San Francisco.
Both from that city, each had recently moved back after living elsewhere for some time. Ms. Bellsey, 36, is now the head of brand programs at Waze, a navigation app, in Mountain View, Calif. Mr. Leonard, 31, is a content producer at Tempo, a fitness-technology company, in San Francisco.
Mr. Leonard, who said he typically runs late, showed up for the date 20 minutes early. To ease his nerves, he ordered a gin martini, which he garnished with his own pickled onion. He had recently become a fan of the Gibson martini, which is made with pickled onions, and had developed a habit of carrying jars of cocktail onions in case a bar didn’t stock them. (He didn’t divulge this to Ms. Bellsey until a later date: “You’ve got to wait to bring all your weird habits,” he said.)
At the bar, the two talked for hours. Ms. Bellsey learned of Mr. Leonard’s love of film and was wowed by his knowledge of San Francisco’s history and landmarks. But it was his chivalry that most impressed her. Each time she stood up, he stood up.
“He’s like Sinatra living into today’s world,” she said.
A second date came the following week. It began at a jazz bar, where Ms. Bellsey arrived to find Mr. Leonard with a Gibson in hand. Afterward, they went to a Halloween party, where they shared their first kiss.
One week later, for a third date, Mr. Leonard suggested a hike at Cataract Falls in Marin County, Calif. Though both had concerns that a day on the trails might be too much time to spend with someone so soon after meeting them, those worries quickly disappeared.
The two chatted through the entire hike and followed it with a wine tasting, dinner and stops at two different bars in San Francisco. They didn’t part until 2 a.m.
“The next morning, I thought, ‘Wow, I haven’t spent that much time with one person in a while,’” Mr. Leonard said. “And I felt like I could just do it all over again.”
The month after they met, Ms. Bellsey took a trip to Paris in November 2019. While she was away, Mr. Leonard sent her long, poetic text messages. Ms. Bellsey awoke each morning eager to read them and made plans to see him on the day she returned.
By the end of 2019, the two were an official couple and in love. For his birthday that December, she home-pickled cocktail onions as a gift. In March 2020, after they took a trip to Tulum, Mexico, Mr. Leonard moved into Ms. Bellsey’s one-bedroom apartment in San Francisco’s Russian Hill neighborhood just as pandemic lockdowns were going into place.
To entertain themselves during evenings at home, they started a Friday night tradition where they would select a country and plan an entire evening around its culture, complete with décor, dinner and dressing in formal attire.
After moving in together came discussions about marriage, and by the summer of 2021, Mr. Leonard was ready to propose. He did so that June at the Timber Cove Resort in Jenner, Calif., on the Sonoma Coast. At sunset one evening, after downing a Gibson, he led Ms. Bellsey down a dirt path overlooking the sweeping bluffs, knelt down and asked her to marry him.
The two were wed on June 18 at Foreign Cinema, a restaurant and outdoor movie theater in San Francisco. Eileen Naughton, a mentor of Ms. Bellsey’s and an affiliate of American Marriage Ministries, officiated before 142 guests. At a reception that followed, tables were named after movies set in the Bay Area, and films including “Roman Holiday” and “When Harry Met Sally” were projected on the venue’s walls.
Now that she is married, the bride, a self-described “active matchmaker,” said she looks forward setting up more couples.