Eleanor Tracy Conroy knew she was in love with Christopher Shay Aitken at age 9. Whether he would be the man for whom she would eventually wear a beloved family wedding dress was not always as certain.
Ms. Conroy and Mr. Aitken are from families with long histories on Cape Cod, Mass. — Ms. Conroy’s in the town of West Dennis and Mr. Aitken’s in Sandwich. They met in 2000 as 7-year-olds at the Hyannis Yacht Club, where both spent summers swimming and sailing.
“Eleanor was beautiful and adventurous” in her board shorts and life jacket, Mr. Aitken said. Romance was in the salt air by August 2002, when they were soon to part ways for fifth grade: On a dare from her cousin and his best friend, they kissed. Ms. Conroy felt the first stirrings of love, though she hadn’t yet reached her 10th birthday.
Then, over AOL Instant Messenger, “we had a tragic breakup,” she said, joking. “The long distance was too much for Chris.”
Mr. Aitken, 32, lived on the Cape year-round. Ms. Conroy, 33, spent the school year in Newton, Mass., with her parents, Mark and Jayne Conroy, and an older sister, Mildred Conroy. A pang to return to West Dennis, where her maternal grandparents had bought a Victorian house with views of Nantucket Sound in the mid-1970s, hit her every fall. And not just because Mr. Aitken lived nearby.
“I looked forward to it because it’s my favorite place to be,” she said. “However many years old you were is how many weeks of the summer you got to spend there, with just our grandparents, no parents.” Joan and William Heimlich also welcomed a band of beloved cousins, the children of all five of their daughters, to their three-acre estate, known as Elmwood.
Ms. Heimlich, now 90, introduced her grandchildren to other family traditions, too. From their earliest childhood, Ms. Conroy and Mildred Conroy remember hearing about their grandmother’s wedding gown and its journey through the brides in their family.
After Ms. Heimlich wore the cap-sleeve dress made by Priscilla of Boston, crafted from the long-lasting silk peau de soie, in 1957, all five of her daughters wore it to their Elmwood weddings. In 2023, Mildred became the seventh Conroy bride to be married in the dress, also at Elmwood.
“I almost think of it like that book ‘The Sisterhood of the Traveling Pants,’” said Mildred Conroy, who now lives in Jackson Hole, Wyo., with her husband, Andrew Parke. “My aunts are all different heights and weights, and we all had to have the dress tailored, but we kept the original style.”
Whether Eleanor Conroy would be the next bride to wear the A-line dress was unknown until last year.
Ms. Conroy is an emergency room nurse at Tufts Medical Center in Boston. She holds a bachelor’s degree in nursing from the University of Massachusetts and is currently studying to be a nurse practitioner there. She expects to graduate in December 2026.
After her preteen breakup with Mr. Aitken, the two reconnected at Tabor Academy in Marion, Mass., where both attended high school.
“We were such incredibly close friends that everyone around us asked, Why aren’t you two dating?” Ms. Conroy said. “We would say, ‘We can’t do it. We’re just friends.’” Even so, they went to senior prom together.
Mr. Aitken, a lawyer and senior compliance officer at the Audax Group, an investment company, kept in touch with her through his four years at Providence College, where he got a bachelor’s degree in psychology before earning a law degree from Brooklyn Law School.
He occasionally brought girlfriends home during those years to Sandwich. His parents, Montgomery and Elizabeth Aitken, have since divorced and moved from the home where he grew up with an older sister, Alyssa Banholzer.
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Ms. Conroy met several of those girlfriends. “Chris always picked very lovely women,” she said. Mr. Aitken can’t be as magnanimous about Ms. Conroy’s past loves, because she didn’t have any.
“He was my only boyfriend, ever,” she said.
Mr. Aitken had moved to the Upper East Side of Manhattan when Covid lockdowns returned him to Cape Cod to quarantine in mid-2020.
Ms. Conroy was caring for William Heimlich, who had cardiac disease, full time at Elmwood. “I needed support from friends,” she said. “I was reaching out to Chris a lot more, calling and texting.”
When it was safe to gather, their families got together at familiar spots around the Cape for dinners and boat trips.
“We would end up sitting together and talking just to each other the whole time,” Mr. Aitken said.
Both were privately acknowledging their friendship had changed in the summer of 2021. That August, Mr. Heimlich died. The same month, Mr. Aitken, who had moved to Boston, planned a boat trip for two to a tiny island known mostly to locals.
Then, “Chris did the brave jump,” Ms. Conroy said.
“I got some canned champagne because glass on the boat can be dangerous, and I asked her to go on a date,” he said.
Their kiss after dinner at the Boston restaurant Barcelona was the first since the childhood dare. But for Mr. Aitken, it was much different. “I was in love,” he said.
Ms. Conroy moved to Boston in January 2022. In March 2024, they moved into an apartment together in the city’s South End, where they now live in a brownstone.
In June 2024, on a morning after Ms. Conroy had worked the night shift as a nurse, Mr. Aitken led her to a boat brimming with flowers at Elmwood and proposed.
Joan Heimlich’s dress was pulled from an Elmwood closet and its Priscilla of Boston bag for an eighth time.
On Aug. 9, Ms. Conroy and Mr. Aitken were married by Martin Conroy, Ms. Conroy’s uncle, who received a single-day certification from the State of Massachusetts to officiate.
The ceremony, attended by 250 guests, was on the lawn at Elmwood, where each bride who has worn the dress married. Mr. Aitken wore a blue wedding suit and something borrowed of his own: his great-great-great grandfather’s cuff links.
Joan Heimlich wiped tears when she saw Ms. Conroy in the dress. But wearing it, Ms. Conroy felt less sentimental than empowered.
“I could feel the strength of my family, all of them in their happiest moment, behind me,” she said just after she and Mr. Aitken were pronounced married.
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