Her father was the venue architect. Her brother helped with the food and beverage selections and her cousin sang at the reception. She was the bride.

📸: Caroline Goddard and Maurisa Mackey (second shooter)

What happens when you cross The Father of the Bride (1991) with All My Life (2020)? A meet-cute that led to a quick engagement and a family-filled celebration of love.

The Meet Cute

The short version? They met through a mutual friend. The long version? Strap in.

Alaina Andreozzi’s friend brought Jack Ostler to a birthday party in New York. Jack was visiting from San Francisco after leaving his job at Facebook, looking for inspiration for his next career jump. The two got to chatting about the Guggenheim and Whitney Museums in New York. After a drink and some career advice, Jack asked for Alaina’s number. “I was oblivious,” she says. “I thought he was talking about the museum.”

On their first date, they walked to the Whitney Museum and followed up with drinks and a burger, a typical date. “But things got real intense really fast,” she says.

Jack had planned to meet up with his cousin in Brooklyn shortly after the date, but neither wanted the date to end, so he invited Alaina to tag along. While at a bar, a massive crowd of people in gowns and suits walked in, and it just so happened to be the Vogue CFDA afterparty. Alaina asked a random stranger what was happening, and after chatting, she realized she was having a one-on-one conversation with none other than musician Leon Bridges. The night continued on until 4 a.m.

The following week, the two were inseperable. Unfortunately, Jack had to head back to California, and they left it at “I’ll see you when I see you” and tried to move forward. However, this wasn’t nearly as easy as it sounded. One month later, after constant chatting, Alaina jumped on a plane to San Francisco. “I barely knew him, but by the time I left, we were going to get married,” she says. When he dropped her off at the airport to head back to New York, they were already planning to move to either city. With the way things moved so quickly, it’s no wonder that her parents asked, “have you joined a cult? You’ve known this man for, like, seven days.”

“We really did just know,” Alaina says.

The Engagement

The couple remained long-distance for a few months while prepping for the near-future wedding. While shopping in Oakland, CA, they found Esqueleto, a shop known for its sustainable rings and curated independent designers. Luckily, the shop was opening a location in SoHo, New York. When they arrived home, they found the perfect ring, but the pandemic hit, and Alaina and Jack moved home to RI for the summer to escape isolation. That fall, the couple moved out to San Francisco as a trial run and continued to check in on the engagement. They wanted both of their families to be together, so they continued to put it on hold.

Fast forward to a few months later when vaccines became available and the world opened up again. They went out to dinner, and while Jack had planned to propose the next morning, the timing just felt right. “It was a fun night, a full moon, and Jack said, ‘We should go on our roof and drink a bottle of wine.’” Their roof overlooked the park where they had decided to be together, and that’s when Jack got down on one knee with the ring from Esqueleto. (Even in the height of COVID, Jack got it from the shop owner’s home in Brooklyn, with safe practices in place, of course.) Untraditionally, Alaina had something for Jack, too: a gold cross pendant. “I had always liked the idea of being in the moment and having an equitable engagement,” Alaina says.

The next day, the couple spent some quality time at Carneros Ranch in Napa, just the two of them. “The silver lining of being alone was the privacy,” Alaina says. “I wouldn’t have wanted it any other way, this little love bubble for twenty-four hours.”

The Planning

Both Alaina and Jack had huge circles of friends, racking up an initial total of 300 guests. Prioritizing those who meant the most to them and observing COVID worries, they narrowed it down to 140. “Jack and I are really intentional about our relationships and wanted to create an experience that felt intimate,” she says. The guests were equally split between those in San Francisco, New York and Rhode Island. “We wanted to interweave those circles.”

While most of the planning went smoothly, there was one hiccup that left them scrambling for changes. The brunch and hotel block was set to be held at the Wayfinder Hotel in Newport. Just six weeks prior to the wedding, it caught fire and closed until further notice. The next morning, everyone got to work, making calls to surrounding hotels to change their accommodations. Her planner, Pamela D’Orsi, found availability at the Atlantic Beach Hotel and Newport Hotel and Suites, a bit pricier than their original plans. In response, some local family members even graciously offered their homes to guests or booked large Airbnbs. Alaina’s parents stepped in and did everything they could to help. “They said, ‘We had our wedding, this is yours.’ It brought us closer together,” she says.

From the get-go, the couple knew they didn’t want a bridal party. “Because this wedding was so intimate, if you were invited, you were a bridesmaid [or groomsman],” Alaina says. To honor their siblings, Alaina’s man of honor was her brother and Jack’s siblings were the best man and woman. “The moment is about cherishing you and your partnership,” she says. “I like the idea of having just us in the spotlight.”

The Venue

Alaina’s father, David Andreozzi, was the architect of the renovations on the Boothden estate. The 1883 Middletown property was originally built for Edwin Booth, famed thespian and brother of the infamous John Wilkes Booth. While Alaina and Jack had always privately dreamed of marrying at the waterside retreat, they never dared ask. They instead explored other options, such as the Tillinghast Place in Barrington, a Rhode Island School of Design private property only available to alumni (courtesy of her father and florist), and Weatherlow Farm in Westport, Massachusetts. While on a walkthrough of Boothden, Alaina’s parents casually mentioned their daughter was getting married, to which they replied, “Are you kidding me? They have to have the wedding here.”

“They’re just natural hosts and such wonderful people,” Alaina says. “It was so meaningful and beyond our wildest dreams.”

A Family Affair

Alaina’s brother is a chef who has worked in Michelin star kitchens in NYC and now owns Pizza Marvin in Providence, RI. Based on his expertise, he was able to help with the food and beverage selection, making sure most offerings supported local businesses. Rather than carrying generic wedding cocktails and beverages, the couple curated a collection of five wine varietals from a local store. Pizza Marvin even created a custom cocktail, aptly named “Bicoastal Crush” to represent Alaina and Jack’s journey.

Alaina’s mother has a background in event planning, so any small details that Alaina and Jack overlooked was brought into the picture. She was actually the first to point out the caterer, Smoke and Pickles, after Alaina had expressed interest in a pig roast. Another unique detail was that Alaina designed the invitations to make it more personable and used New England Invitations to print and send them to her guests.

To top it off, Alaina’s cousin, Jay Rosie, sang for the ceremony to emphasize the importance of family and local talent.

The Highlights

During the cocktail hour, to Alaina and Jack’s surprise, David had an airplane fly over the guests with a banner that read “Congratulations Alaina and Jack.” The residential party next door even cheered them on.

Something special was that Alaina’s grandmother was included in the horah for the first time in her life and was lifted into the air by the groomsmen, since she had her bar mitzvah later in life.

While the guests were having a grand time, Alaina’s parents got an outsider’s view as they looked on from outside the tent and danced alone. “They got to cherish what they’ve built and what they’ve accomplished,” Alaina says.

Although the ceremony was in the summer, Alaina’s dress had long, flowy sheer sleeves and a plunging v-neckline. “I didn’t even think about what dress works for each season,” she says. “I just wanted to feel the most like me and I didn’t want to feel like I was in a costume.” She was immediately gravitated toward the balance between a sensual and empowering neckline while keeping a classic sleeve.

At the entrance to the reception area, Alaina’s friend Kate created an art installation in the tree: a pink cutout plastic hanging installation, just another way to highlight talent of those she loved.

Remember the encounter with Leon Bridges on the first date? Their first dance song was “River.”