When Jacqueline Anne Morison Heath ordered a dirty martini made with Hendrick’s Gin and three blue cheese-stuffed olives, it piqued Matthew Joseph Swain’s interest. That was his exact cocktail order — right down to the number and type of olives.
It was August 2022, and the two were at a private dinner club called Tiro A Segno of New York in Greenwich Village, where their companies were celebrating a business deal. Heath and Swain chatted for two hours over the meal, then another three at a bar.
Swain suggested they meet again sometime. “In order to do that, you need to have my number,” Heath remembered countering. “You can’t just throw that into the world and then not have a real pathway to realize that statement.”
Duly chastened, he took down her information.
At the time, Swain had recently been named, at age 27, the global chief executive of the private equity firm Triago, for which he was based in New York. Heath lived in her native Toronto and also worked in private equity. A few weeks after the work dinner, they had their first date when Swain made up a reason to see clients in Toronto. They found business excuses for a second date in Chicago, and a third in Detroit.
[Click here to binge read this week’s featured couples.]
Swain, now 31, grew up in Greenwich, Conn., and received a bachelor’s degree in environmental studies from Colgate University. He is the global co-head of equity capital solutions at the investment bank Houlihan Lokey, which acquired Triago in 2024.
He was captivated by the trajectory of Heath, 32, who lost both of her parents before she was 18. She went on to earn dual bachelor’s degrees in economics and philosophy from Trinity College at the University of Toronto. “On top of that, she’s successful in the male-dominated industry of private equity,” Swain said. “She’s a killer, and incredibly smart.”
Neither were shy about jumping on planes to see each other so soon. “Matt is very intense and straightforward about what his objectives are,” Heath said. “It was pretty explicit from the get-go that we were both interested in exploring what was there.”
But the force of that interest, and the long distance, soon proved a problem at work, especially with the pressures of Swain’s still-fresh chief executive position. “It was becoming too difficult, and people at the company were even noticing I was fairly distracted at the time,” Swain said. He broke it off over the phone in October 2022, then flew to London that night.
The split lasted the seven hours of his flight.
“The first thing I saw when I landed was three Air Canada planes. I’m not much for signs, but this was definitely a sign,” he said. He texted her an image of the planes, and Heath quickly forgave his “lapse in creativity” in making their distance work.
He then invited Heath to spend a weekend in Nantucket, Mass., where he has a home and centuries of family ties: His ancestor John Swain was one of the first European settlers of the island in the 17th century. A street and wharf are named in his honor.
“I learned very quickly that Nantucket is Matt’s place,” Heath said. “His disposition changes when he’s there. It really is such a magical island.”
It was there, amid the boat rides and stops at oyster bars, as he watched Heath fall in love with his favorite place in the world, that Swain first realized he might spend his life with her.
They maintained their relationship between New York and Toronto until the spring of 2024, when Heath accepted a role in New York. She is now a vice president at Seven Point Equity Partners. That September, Swain proposed on a Nantucket dock, surprising her first with their families waiting at the Wauwinet, a resort nearby, and then with friends at the Nantucket Yacht Club.
“I wanted her to feel a lot of love and warmth around her,” Swain said.
On Sept. 19, they were married at the Nantucket United Methodist Church by the Rev. Jackie McGrady, an Episcopal priest. A reception followed at the Nantucket Yacht Club.
At the rehearsal dinner, Swain presented Heath with a lightship basket, a traditional handicraft that whalers made during long trips at sea. Theirs was passed down from his grandmother to his mother to Heath, with their names and years of conveyance etched into the ivory of the lid.
“It’s pretty amazing to already feel so included in the inheritance of this family,” she said.
The post A Very Specific Martini Order Leads to Something More appeared first on New York Times.
