Connor May originally planned to propose to Kaitlin Brown, his girlfriend of three years at the time, after they had finished swimming 1.2 miles, cycling 56 miles and running 13.1 miles together. Competing in a half-Ironman triathlon, he thought, would be an important milestone and a fitting preamble to their engagement.
Without revealing his ultimate goal, he began to work out the details with Ms. Brown, who was looking for a new challenge after competing in several marathons and shorter triathlons. With a little research and some debate — Ms. Brown wanted to do a half Ironman in Dubai — they settled on a race in Oceanside, Calif., in April 2020 and began to train.
They were both bitterly disappointed when the pandemic intervened and the triathlon was canceled. Ms. Brown, a retail planner at Equinox, the fitness company, was particularly upset. She had prepared for the race with great fervor, waking up each day at 4 a.m. to exercise for two hours before work. “I was putting my body through hell,” she said. “I was so exhausted.”
Athletic achievement is in Ms. Brown’s blood. Her father, Doug Brown, was a two-time Stanley Cup winner during a 15-year career in the National Hockey League, and her maternal grandfather, Wellington Mara, was an owner of the New York Giants football team until his death in 2005.
Mr. May’s dismay had relatively little to do with losing the opportunity to test himself physically. (His own training, he said, had been relatively lax.) He now needed to find another way to ask Ms. Brown to marry him that fit their relationship.
“We aren’t really a lovey-dovey couple,” said Mr. May, a vice president of Guidepoint, a research services firm in New York. “We’re not like professing our love to each other with passion and fire.” For them, grand gestures and cinematic flourishes are far secondary to organic, steady growth; concrete achievements; and the subtle but powerful intimacy that comes from building a shared life.
Eventually he settled on a less grueling physical activity, a hike at Bear Mountain in the Hudson Valley in March 2020. Ms. Brown, 27, was still inclined to stretch herself. “She wanted to do like a really long, like five-mile hike,” Mr. May said with a laugh. “I kind of pretended like I didn’t know where to park so we did maybe a half-mile hike instead.”
The timing surprised Ms. Brown, a Boston College graduate. When the triathlon, which she suspected might be accompanied by a proposal, went by the wayside, she assumed Mr. May, also 27, would wait until after he had completed his two year M.B.A. program at Columbia Business School. “I had no idea until we were getting to the top of the mountain and he asked to hold my hand,” she said. “I was like, ‘What on earth is happening?’”
After they became engaged, the couple, who left the city to live with their respective parents in Westchester County during the pandemic, moved into an apartment together in Larchmont, N.Y. “I think that move really just kind of put us on that next level of adulthood,” Mr. May said. “We got a car, we got a dog and now we’re living this suburban lifestyle.” These were maybe less dramatic milestones than finishing a half Ironman, but they sprung from the same desire to mature together through dedication and discipline.
Ms. Brown and Mr. May were married on July 1 by the Rev. Thomas Collins, a Roman Catholic priest, at Our Lady of Sorrows Church in White Plains, N.Y. in front of their parents and siblings. The next day, at Blue Hill at Stone Barns in Pocantico Hills, N.Y., a nearby town in Westchester, they held another Catholic ceremony and a reception for 70 guests.
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