When Kelleigh Anne Whelan moved to Miami after graduating from Harvard Business School, her goal was to find community. “I was focused on work and went to Harvard alumni events and tried to meet people to see who I clicked with,” she said.
At an alumni event in October 2022, she was talking to Patricia Pechter. During one conversation, Pechter asked Whelan what she was looking for in a romantic partner. “I don’t think I ever crystallized what my type was,” Whelan said. “But for whatever reason in that moment I said, ‘Someone who’s confident but kind.’”
Someone instantly came to mind for Pechter: Her boss, Justin Alexander Holland.
Though Holland was not dating at the time, he recalled thinking, “I was open at any moment for lightning to strike.”
On Dec. 16, Holland sent Whelan a text, and two days later, their first date was at the now-closed Red Carpet Italian Restaurant in Miami. “I was struck at the beginning by how much we had in common, from her ambitions to just the amount of nerdy stuff we talked about, whether it was A.I. or technology,” he said. “Also, I could really tell she was kind.”
Holland, 42, is the founder and chief executive of HealthJoy, an A.I.-powered health care navigation platform based in Chicago. (Patricia Pechter, who introduced them, is the chief medical officer.) He was born in Clark Air Base on Luzon Island in the Philippines, and received a bachelor’s in mechanical engineering from the Massachusetts Institute of Technology.
Whelan, 34, is a strategic adviser to Barry’s, a boutique fitness company based in Miami, and builds consumer tech. She grew up in Ridgefield, Conn., and received a bachelor’s degree in mathematics and psychology from Northwestern University and an M.B.A. from Harvard Business School.
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Months later, they regularly saw each other and traveled together, including a weekend at the Breakers in Palm Beach and a trip to the Dominican Republic. “Our early dates were a series of escalating adventures,” Whelan said. “It quickly became clear we weren’t two people who would slow each other down.”
In April 2023, they joined friends for a sailing trip through the Exumas in the Bahamas, with the group traveling together on two catamarans. Holland, who had experience living on a sailboat, was one of the captains. One afternoon, while Whelan and Holland were snorkeling, they saw two sharks moving toward them.
“I was more scared for him than I was for myself,” Whelan recalled. “I thought, ‘Nothing can happen to him.’” In the water, Holland pulled her close, positioned himself between her and the sharks, and confidently guided her back toward the boat. “My focus was just making her feel safe,” he said.
For Whelan, the frightening encounter also brought clarity to the depth of her feelings.
“In that moment I thought, I love this person with all my bones and would do anything to save and protect them, and I could see myself with him forever,” she said.
Later that year, they moved in together to the Edgewater neighborhood in Miami. In July 2025, they moved to Tampa, Fla., where they currently reside.
During a summer trip to Highlands, N.C., on Aug. 27, 2024, they went on a hike, and as they stopped to view the mountain, Holland proposed.
Almost two years later, on Aug. 26, Anita Rosete, the deputy clerk with the Hillsborough Clerk of Court & Comptroller, officiated a legal ceremony at their home in Tampa. Holland’s parents, Nancy Ruth Holland and Charles Robert Holland, were witnesses.
Two months earlier, on June 27, the couple had hosted a larger wedding celebration on the rooftop terrace of Reid’s Palace, a Belmond Hotel, in Madeira, Portugal, before 134 guests. Whelan walked down the aisle with her mother, Lisa Anne Whelan, to “You’re So Cool” by Hans Zimmer. Holland’s best friend, Adam Cohen, who was ordained by American Marriage Ministries for the occasion, officiated.
During the wedding weekend, guests were guided by Alfred, an A.I. butler that Whelan spent about 40 hours building to answer questions and help manage logistics via text messages. “Building this connected Justin and me so much because it allowed us to lean into our skill sets,” Whelan said.
Holland added: “We’d fallen in love two years before, and that day was a function of celebrating what had already been there, inside us, for a long time.”
The post After a Frightening Shark Encounter, Their Feelings Became Clear appeared first on New York Times.
