In 2016, Matt Williams left Manhattan and moved to Brookline Village, where Ryan Joy O’Connor had lived for five years. The two went to the same coffee shops, said hello to the same people on walks, and popped by the same stores. They even lived right across the street from each other – Ryan could literally see Matt’s apartment from her window. In the four years Matt lived in the Village, the two never met.
8 years later, under the just-illuminated Holiday Lights, surrounded by revelers, Ryan and Matt would be engaged at one of Boston’s favorite holiday traditions.
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Born in Boston, Ryan and her family moved to southern New Hampshire a few years after the arrival of her younger sister. The oldest of four children, she was born with a complex congenital heart defect and has been treated at Boston Children’s Hospital her entire life. She has undergone five open-heart surgeries – the first when she was a newborn – and was seen at Children’s regularly, venturing into the city for clinic visits, tests, and procedures multiple times a year. While most would be riddled with anxiety, Ryan looked forward to the opportunity to visit Boston. Her parents empowered her to speak directly with doctors, asking questions and taking ownership over her care, while also encouraging her to treat the day as a chance to enjoy her favorite city. It would never be “we’re going to the hospital”, it was “we’re going to Boston.” After an appointment ended, Ryan would spend time in the Public Garden, weather permitting – a core memory: riding the Swan Boats on a warm spring day. She would then head off to one of Boston’s famed museums – a highlight: the Museum of Science. After attending college in Virginia, she moved to Boston immediately following graduation to serve as an AmeriCorps Fellow. She lived in Fenway for one year before moving to Brookline Village in 2011, where she has lived since.
Growing up, at first in the suburbs of Philadelphia, Matt and his family had the unique opportunity of calling a variety of international cities – from Tokyo, to Dublin, to London – home. He eventually made his way back to Pennsylvania for college, ending up in New York City after graduating. Around the same time that Ryan moved to Boston, Matt’s family, who had spent time on the Cape throughout his childhood, bought a house in Chatham. Growing tired of the fast-paced nature of New York, Matt had grown fond of his time spent in Boston when visiting his parents and friends and decided that Boston was next. His move to Brookline Village followed.
Ryan & Matt pose for a portrait in the Public Garden
Matt runs the Boston Marathon for the Boston Bulldogs in 2024
On a normal Memorial Day weekend, Ryan and Matt would be down Cape – Ryan in Wellfleet, and Matt in Chatham – but Memorial Day 2023 saw them both remain in Boston for the weekend. The two matched on Bumble and agreed to meet that Sunday morning. Unaware that the two had ever lived near each other, Matt suggested Brothers & Sisters Co., a favorite spot of his from his time in Brookline Village (Matt had since moved to Newton Centre). Ryan, living right above the coffee shop, played it cool, making sure Matt didn’t see her name on the mailbox when they met up. The two hit it off immediately, discovering that they once lived right across the street from each other – one of many anecdotal stories of times that the couple could have, should have, or would have met before that fateful Memorial Day weekend.
Ryan and Matt’s love story is one forged through a mutual and deep appreciation for the sights and sounds of Boston. For their second date, the two enjoyed a Boston Pops Concert, scoring second-row orchestra seats. Their third date saw them take to Harvard Square for the annual Dragon Boat Festival, stopping at the Harvard Art Museum afterward. The couple have seen concerts at Fenway, played pickleball on the Lawn on D, dined at the top of the Prudential Center, hit up the Boston Harbor Hotel for Rat Pack Wednesdays, learned how to curl by the Seaport, centered their chakras with yoga and Concerts in the Courtyard at the Boston Public Library, and posed for live portraiture by an artist in the Public Garden. Both even ran the Boston Marathon – Ryan in 2015 for Boston Children’s, and Matt in 2024 for the Boston Bulldogs. To say the two love Boston, and all it offers, would be an understatement.
Ryan & Matt at Chatham Jewelers, where Ryan’s ring was designed
Just before Ryan’s fifth open heart surgery
Ryan knew a proposal was coming – the couple had a ring designed in Chatham that summer. But, right before their one-year anniversary, she learned that her heart was not doing well. After several procedures, she was told it was time for her fifth open-heart surgery. Ryan felt ready – she’d done this before – but it was her first time going through it with a partner. Due to the nature of the surgery, the couple questioned whether it would be better to get engaged before or after, and settled on after. Ryan, as she has many times before, endured bravely. Ryan notes that this kind of intensive medical treatment can cripple couples, but instead, it brought her and Matt closer. Eight weeks after her 5th open-heart, she was engaged to Matt on the Commonwealth Avenue Mall.
Ryan is an acolyte of romance and Christmas, making the Holiday Lights ceremony the perfect backdrop for the proposal. The couple had joined Friends of the Public Garden for the Holiday Lights ceremony in 2023, a week after their six-month anniversary. Why is this the best backdrop for an engagement? “They flip the switch, it all lights up and you can see everyone, and it feels like the whole city is there together for the holidays,” said Matt.
Like a true Boston native, surprises are hard to get by Ryan. Executing Matt’s Holiday Lights proposal plan required deft planning, tactful coordination, excellent timing, and a pinch of luck. “I had NO idea it was happening,” Ryan shared. Ryan had screenshotted the Holiday Lights announcement on Instagram, sent it to Matt, and suggested they make a reservation at Contessa prior to the lighting ceremony, as they had done the year before. Unbeknownst to Ryan, Matt had already planned this all out, including the reservation at Contessa before the Holiday Lights came on. In Ryan’s mind, she had suggested the entire evening, spur of the moment, laughing “in hindsight, you cannot get a reservation at Contessa a week out.” She counted out the possibility of the proposal entirely.
Ryan’s sister, Red, and her two children were key to the evening going off without a hitch. Ryan regularly treats her niece and nephew to days out in Boston, where fun is the mission, and often involves a stop at the Make Way for Ducklings sculpture in the Public Garden. Anticipating their evening under the Holiday Lights, Matt had her sister plant information with the children, suggesting that Matt might surprise Ryan with a proposal at the annual Holiday Pops concert. On a trip to Boston before the proposal, Leland, the older of the two, shared excitedly “we have a surprise for you at the Pops!” Thinking it was a reference to a possible Christmas gift, Ryan replied “we have a surprise for you too!” Leland was persistent. “Auntie RyRy, we have a surprise for you at the Pops!” Lulu, honest and deadpan, corrected her sibling “It’s not a surprise from us, it’s a surprise from Matt.” Thanks to this genius strategic move, Ryan now believed Matt would propose at the Pops.
After some tight choreography to ensure that Ryan didn’t see her family, who traveled in for the proposal, the two made their way from Contessa down to the Mall and into the crowd. Ryan was freezing – they almost considered leaving – but Matt was persistent, ensuring he would wrap her up and keep her warm. The countdown began and, once the lights came on, Matt turned Ryan around to face him. His heart was pounding. Ryan was genuinely shocked. Once he got down on one knee, a giant crowd formed a circle around them, straight out of a movie. “The whole night was perfect, to be under those lights…I will remember that night forever,” said Ryan.
“Did you see that couple get engaged?”, “Please tell me you saw that!” The crowd loved it. Cheers erupted. In a video of one angle of the proposal, four young men in the background slowly realize what’s happening, and it is visible on their faces almost immediately. One puts down his coffee, one takes off his gloves to clap. One even begins jumping up and down, cheering. One by one, Ryan’s family and friends begin to emerge from the circle. Ryan and Matt’s proposal illuminates what makes Boston, and these cherished parks, most special: when the city comes together in community – like it does every year under the glow of the Holiday Lights – magic happens. Ryan pauses, “to me, these parks are the heart of the city.”
When Ryan first moved to Boston almost 15 years ago, she lived on Queensberry Street in Fenway. While she and Matt were driving to an appointment at Boston Children’s, they found themselves by her old neighborhood. Over the summer, the city had installed banners on street lamps across the Fenway, promoting its cache as a cultural destination. Installed on the banner were catchy slogans… “The Fenway,” “The Art Way,” “The Head Way,” The banner on Ryan’s old street caught her eye, as it featured a large-scale illustration of an anatomical heart. She wondered aloud, offhand, where the banners go when they are retired.
Matt heard her loud and clear. For Christmas, just weeks after they were engaged under the Holiday Lights, he tracked down the City department responsible for the banner and secured the exact one that drew Ryan’s attention: The Heart Way.
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