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In a time when couples typically connect through apps and direct messages, Jessie Cai and Phil Comerford’s digital meet-cute is both the epitome of modern love and a nod to a simpler time. “We actually first traded e-mails back in April 2010 when I was trying to sublet Phil’s apartment for the upcoming summer,” Jessie explains. “We finally met in June 2010 when we were interning in New York City as juniors in college.”
Phil proposed to Jessie in August 2019, nearly ten years after they took their connection from HTML to IRL. “We love to travel, and Phil prepared a photo book of all our travels together over the past 10 years as a belated 30th birthday gift,” she shares. “The last page of the book–which had a decade’s worth of memories [as well as] letters from my parents, sister, and friends–was [a note asking] if I would be his forever travel buddy.”
Though Jessie and Phil love to explore the world, they wanted to keep their June 26, 2021 nuptials local. The couple ultimately selected Lion Rock Farm in Sharon, Connecticut, which is close to Hudson Valley, one of the couple’s favorite destinations.
“We wanted to bring out the best of Hudson Valley during the summer—with an elegant, but light [and] fun feel to the weekend,” the bride shares. “We also wanted to incorporate elements of our life—friends, family, cultures, cooking, hiking, and traveling—blending together.”
With a ceremony that honored both of their backgrounds, a menu filled with fresh and seasonal ingredients, and 152 of their closest friends and family members, it’s safe to say their mission was accomplished. Learn more about the couple’s special day, as planned by Nicole Sheppard of All Who Wander Event Design and photographed by Sasithon Photography.
“We wanted the color to feel bright and summery for the big day,” Jessie says. “It was important that we incorporated some pinks, purples, and lots of green to bring out all of the amazing gardens at the venue.” The couple set the groundwork for their special day with whimsical invitations from Fourteen-Forty. “I loved working with Fourteen-Forty on designing our invitation suites and menus,” she adds. “It really felt like us.”
When it came to selecting a venue, it was love at first sight—literally. “Lion Rock Farm was actually the first venue we saw in person and we fell in love,” the couple shares. “We were also obsessed with the exclusive caterer there and loved that you could bring in your own alcohol and make the venue your own. They have the most gorgeous peonies and flowers growing on the farm.”
The groom dressed up in a black tuxedo from Enzo Custom, complete with suede loafers from Del Toro and cufflinks. “Pretty easy and low-key,” Phil shares. “The hardest challenge was making sure I tied the bow tie correctly!”
Jessie and her inner circle got ready for the big day together, sipping some bubbly in the process.
The bride stunned in a floral appliqué dress from Mira Zwillinger. Due to the ongoing pandemic, Jessie shopped for her wedding dress by herself. However, she found a lot of solace in the solitude. “It ultimately felt like a very ‘me’ decision: no pressure, no care in the world,” she explains. “It was the first dress I tried on and knew immediately. I tried on other dresses for good measure, but always knew this was the one.”
She accessorized her look with Jennifer Behr jewelry, shoes from Cult Gaia, an updo from Upstyle, and makeup by Makeup Therapy. “I definitely wanted to feel natural and myself,” Jessie shares. “Four years ago, my best friend got married and I was in the wedding party. After that, I was sold on having Tara [of Makeup Therapy] be part of my big day and flew her from Los Angeles. I’ve seen too many horror stories with makeup and it’s easy to not feel [like] yourself. Even my mom and my mother-in-law said they’ve never felt more beautiful in their lives.”
The couple shared an intimate first look before their ceremony began.
No matter what the situation was, as long as we could get married, that’s all that we needed.
After being engaged for nearly two years, the couple was thrilled that they were that much closer to becoming husband and wife. “We almost shifted the date back, but we’re so glad we didn’t as it ended up being one of the few carefree weeks,” the bride recalls. “We ultimately said no matter what the situation was, as long as we could get married, that’s all that we needed!”
The groomsmen took a cue from Phil and sported their own tuxedos. “We wanted to keep it easy for the groomsmen, so the only requirement was a tuxedo, black shoes, and white shirt,” the couple notes. “All the groomsmen already had a black-tie [ensemble, making things] pretty easy.”
As for Jessie’s bridesmaids? The dress code was “choose your own floral.” “I thought floral was light, fun, and [would] fit in with the [summery] Hudson Valley vibes,” she explains. “I also really wanted to make sure my bridesmaids all felt [like] themselves and could even rewear their dress.”
“Ivie Joy, our florist, built us an epic ceremony installation that looked like it was growing out of the ground,” Jessie says. “We wanted to utilize the large tree on the property without it feeling too plain, and Ivie delivered a colorful growing half arch that made such a beautiful impact.” The lush archway was complemented with bunches of sunset-hued blooms and candles of varying heights.
Phil was escorted down the aisle by his parents to the tune of Ed Sheeran’s “Perfect.”
The bride walked down the aisle to “Canon in D,” with her parents on each side. “My sister [walked] down with Phil’s siblings right before,” Jessie adds. “It was so special as I am the oldest daughter and first to marry!”
[It was incredible to look] out to everyone in our life who showed up.
“[It was incredible to look] out to everyone in our life who showed up from all walks of life while we were at the altar: family, friends from high school, coworkers,” Jessie shares. A light sprinkling of rain brought luck to the wedding ceremony.
With personalized vows, a Christian reading, and a small Chinese tea ceremony, the nuptials were a perfect mix of the couple’s unique backgrounds.
Before making it official, the couple slipped on wedding bands from Lauren B Jewelry.
The newlyweds recessed down the aisle to Ray LaMontagne’s “You Are The Best Thing.”
Fortunately, the couple was able to have some alone time before the party kicked into high-gear. “[We spent] five minutes after the ceremony together,” the bride shares. “We sneaked off with some of our apps and just freaked out that we actually got married!”
Speaking of food, the couple worked closely with catering company Hunt + Harvest to create their dream menu. Kicking off the feast was a smattering of starters such as mini Maine lobster rolls, black truffle and gruyere grilled cheese bites, and summer melon skewers with crispy prosciutto and mascarpone. The reception also featured roasted Hudson Valley duck and wild striped bass for the main courses, as well as a tequila bar guests could visit all night long. “The Cai-Tai was the signature drink we used for all of the bars,” the bride shares. “It was made with Casamigos Blanco, club soda, jalapeño, and a splash of grapefruit juice. We also had Mou Tia, which is a famous Asian liquor for those who could handle it!”
“For our seating chart, we also made a colorful board where people could pick a ‘boarding pass’ to Lion Rock Farm and to put their dancing shoes on,” Jessie shares. “We love to travel and thought this would be a cute way to incorporate [that].”
The reception area was the perfect extension of the altar with lush, colorful flowers, acrylic chairs, and tall candles. “We worked with Ivie Joy and Stortz Lighting to complete our wedding planner’s vision for a greenery filled ceiling under a clear-top, twinkling tent,” the bride says.
Though the ceremony featured a live musical trio, a 10-person band called Michael Hart Band from Hank Lane performed throughout the reception. “We had seen them at a friend’s wedding and when we left we thought, ‘Wow, we just went to a concert. We need this band,’” the bride shares. “That was probably one of the easiest decisions we made. We didn’t give them specific songs to play, but said we trusted them and let them play whatever they thought would be best. It really felt like a concert, which we really needed after a long year of Covid-19!”
The couple shared their dance to the remix of “Conversations in the Dark” by John Legend and Edward Sharpe and the Magnetic Zeros’ “Home.”
The 152-person party clinked glasses after thoughtful speeches from the couple’s friends and family.
Jessie and her father enjoyed a solo dance, while Phil and his mother swayed to Stevie Wonder’s “You Are the Sunshine of My Life.”
“This was the first wedding we—and many of our guests—went to in over a year given Covid-19,” Jessie notes. “The dance floor was amazing, and it was so great to finally be with [our] friends [and] family.”
Of course, no wedding is complete without dessert. The couple tapped By The Way Bakery to create a three-tiered, gluten-free cake, made with chocolate, vanilla chiffon filling, and frosting. “[We] topped it off with double chocolate ice cream sandwiches, summer blackberry pie bites, and ‘lunchboxes’ to-go for late night,” the bride adds. “Think PB&J sandwiches, Capri Suns, gummy bears, Goldfish, and chocolate chip cookies.”
Planning a wedding can be an understandably stressful endeavor; however, the couple shares that it actually brought them closer. “We really bonded during our planning process—from exploring what was important to us, to writing our vows to spending time with one another’s families,” the bride reminisces. “It was also so seamless as we had our incredible planner Nicole, who became family to us during this time.”