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The Big Day

Their engagement began with two surprise marriage proposals on the same day

Six years after their first date, Matoaka Kipp and Eli Cotton’s City Winery wedding was packed with pop, pride, and perfect choreography

Cambridge residents Eli Cotton and Matoaka Kipp wed at City Winery on June 15, 2025.Jasmine Jorges

Read more from The Big Day, The Boston Globe’s new weddings column.

On April 10, 2019, Matoaka Kipp was having a great first date.

Eli Cotton — the friend of a friend she finally agreed to meet after months of hesitating — had turned out to be attractive, attentive, and a surprise.

“I remember seeing them and thinking, ‘My god, I’m not prepared,’” the Baltimore native remembers. “I felt like I was a little out of my game.”

Their mutual friend Emily — Matoaka’s childhood camp counselor, Eli’s then-boss at a Charlestown nonprofit — had been trying to set them up for months. Eli was game: “Nobody likes first dates, but I really do.”

The couple brought artichokes to the wedding venue, a food that had become tradition for them on special occasions. They wore flower-shaped pins instead of boutonnieres.Jasmine Jorges Photography/Jasmine Jorges

But it took matching on Hinge before Matoaka, who had been wary of dating after a breakup, agreed to meet that Wednesday night. Matoaka remembers Eli asking a “bajillion questions” over bubble tea and fried chicken at Double Chin in Chinatown.

“I’m usually the person who guides a conversation in my dating life,” she explains. “I couldn’t get one question in.” (When Matoaka debriefed Emily after the date, Emily replied, “Energizer Bunny, right?”)

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“I am an Energizer Bunny," says Eli, who grew up in Newton. “I’m annoyingly one of those people that wakes up and doesn’t need to snooze my alarm.”

The questions, Eli chalks up to nerves, “which was new for me.”

The couple had custom suits made by Boston-based 9Tailors — each knew which colors the other had picked, but seeing each other in their full suiting was a total surprise on the wedding day. The dress code for guests was "vibrant and colorful cocktail."Jasmine Jorges Photography/Jasmine Jorges

Three hours later, the two embarked across Seaport Boulevard for a stroll along the Harborwalk. “I want to bring you to my favorite view in Boston,” Matoaka told Eli.

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She stopped at an apartment building by the New England Aquarium. It was a clear night, but the sun had set hours before. They shared a darkened view and a welcomed kiss — with a fortuitous footnote.

“I didn’t have the heart to tell her that she brought me to my parents’ doorstep,” says Eli.

(Eli told Matoaka as they walked to their respective T stops — assuring her that their parents would have been “genuinely excited” to have accidentally crashed their first date.)

The couple had a first look on the rooftop of an apartment building next to City Winery, but also did a first look with their families, who all turned to see the couple enter at the same time.Jasmine Jorges

Three days later, they had their second date — tacos at Casa Verde, and a walk around Jamaica Pond. On their fourth, Matoaka arrived at Eli’s Jamaica Plain apartment with a pair of artichokes, a gift. They boiled and ate them, which would become tradition for the couple, says Matoaka. “A symbol, especially when we’ve had a bad week or [have] an anniversary coming up.”

They’d known each other for two weeks when Eli asked Matoaka to be their plus one at a friend’s Washington, D.C., wedding. Thanks to a photographer who was “a little obsessed with us,” says Eli, the new couple received dozens of photos from the dance floor.

And 16 days after their first date, Matoaka and Eli exchanged “I love you”‘s in her Watertown bedroom.

“And I know that we both knew before that,” Eli says.

Eli with their parents Cathy and Harvey Cotton. Blocks from where Eli and Matoaka had shared a kiss on their first date, Eli’s grandmother Jeanne Smith met her long-term partner in 1977. The couple now live in what was once Jeanne's Cambridge home.Jasmine Jorges

In January 2020, Matoaka began to chronicle their shared life in a journal.

"You’re cooking right now … I’m watching you cook, and this is what you’re making … and it smells great," she says, ad-libbing a sample entry. She continued to write, suspecting it was an instinct that the relationship was for the long run.

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“I didn’t write down the big moments, just the everyday. Those are things you don’t remember, and they’re the best memories.”

Matoaka gave Eli her journal when she proposed one Saturday morning in June 2023.

Matoaka and her mother, Jenna Weiss, a seamstress who made a custom chuppah for the ceremony. She also provided the rings the newlyweds exchanged; Matoaka notes they come from a long line of jewelers, and a family ring was a personal "must."Jasmine Jorges

It was a quasi-surprise: Both partners wanted to propose and a planned vacation and Pride Month had narrowed their window to late June.

The journal was three-quarters full when Matoaka recruited Eli’s childhood friend Caroline to hide a re-bound edition in the new releases stacks (under C for Cotton) at the Cambridge Public Library, where they planned to pick up books before a weekend trip.

Eli spotted the journal right away, opening it to a marriage proposal from Matoaka, who watched Eli read the letter and then presented a ring.

While an app helped them plan an official first date, the couple attribute the first person that tried to set them up, Emily Grilli-Scott, center, as their true matchmaker. Emily co-officiated the wedding with Eli's childhood rabbi.Jasmine Jorges

“It’s a library,” says Eli, “but anything can happen in the library, obviously.”

It was joyfully unexpected, but Eli was, in part, distracted by Caroline hiding in a nearby stack to capture the moment on camera: “I played it really cool because I was like, ‘My god, you’re supposed to be at my apartment setting up my proposal!’”

Unaware of Matoaka’s plans, Eli had asked Caroline to prep the couple’s Cambridge apartment while they were out. Eli rushed to open the front door first and took a knee when they, relieved, found the pair’s well-used Scrabble board set up to spell out “Will you marry me?” (Caroline had recruited another friend, Maddie, to sub in for her.)

Getting engaged and married during Pride Month was important to the couple; as was hiring queer- or people of color-owned businesses and vendors for their wedding. This included coordination and DJ team, MadLove, and 9Tailors, who created custom suiting for the couple.Jasmine Jorges Photography/Jasmine Jorges

Matoaka, 31, and Eli, 32, wed on June 15 at City Winery in downtown Boston.

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Inspired by their love of live music and large guest list, the couple chose the venue for its central city location and stellar sound system. The ceremony was co-officiated by Emily and Rabbi Andy Vogel of Temple Sinai in Brookline, where Eli’s family are lifelong members.

While neither partner identifies as religious now, Eli grew up Jewish, and both prioritized incorporating traditions that reflect their values.

“I think for a lot of people, religion and queerness is not always a great relationship. … but [Rabbi Andy] was so willing to work with us to change the language to be gender inclusive,” explains Eli.

Their friends (from left: Caroline Rosa, Maddie Freeman, Michael Freeman, and Colby Kyes) performed “The Lonely Goatherd” from "The Sound of Music" for the newlyweds. The act was to make good on a text Eli had (jokingly) sent early in their courtship, requesting Caroline and Maddie perform the song at their future wedding to Matoaka. Jasmine Jorges

The newlyweds wore pins in the shape of cosmos flowers by AIRI designer Maya Alia and rings that had originally been exchanged by Matoaka’s mother and late father. For the ceremony, Eli’s friend Laura walked the rings down the aisle in a Fishwife tinned fish can before Matoaka and Eli said their “I do”s. Matoaka’s mother hand-sewed the couple’s chuppah, inspired by the progress pride flag and stitched with fabric from milestone attire that members of their families had worn.

DJ Melinda Long of MadLove’s playlist was heavy on “the great gay pops,” at the couple’s request. Their first dance was a swing-rumba to ABBA’s “Take a Chance on Me.” Their last was to “Miracles Happen” by Myra from “The Princess Diaries” soundtrack.

For their first dance, the couple took dance lessons from a teacher in Cambridge. Their teacher was from Denmark, and was "so offended" when the couple asked if she had heard of ABBA. They remember her reply: "I am ABBA."Richard Bidgood

“It was hour four, and there were still a hundred people on the floor,” remembers Matoaka.

The exhausted newlyweds left around 1 a.m. while the karaoke played on. But Matoaka and Eli are already dreaming about their next chance to tear up the dance floor.

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“I hope we keep having parties to celebrate community,” says Matoaka. “I think that everyone should have a reason to throw a party. It doesn’t necessarily need to be marriage, but marriage is a really good reason to do it.”

Read more from The Big Day, The Boston Globe’s new weddings column.


Rachel Kim Raczka is a writer and editor in Boston. She can be reached at [email protected].