This Surprise Proposal Party—Disguised as a Photo Shoot—Featured a Riot of Colors and Wedding-Worthy Details

A work trip in the summer of 2018 brought Melissa and some colleagues to a highly recommended restaurant in Seattle, where she was greeted by Matt, the handsome, hilarious, and intriguing mixologist behind the bar. "Matt put on a show for me and my co-workers and as the group left that night, I whispered to my teammate, 'I think I'm in love with that bartender.'" Five days later, Melissa waltzed back to the bar with a wingman in tow to spend more time with Matt, and after, the captivated couple-to-be stayed in touch. The following summer, Matt flew east for a quick visit to see her in New York City, and never left. "It was one of those 'fate' type situations, which I honestly didn't really buy before meeting Matt," says Melissa. "From the night we met, I kept being pulled back to him."

Fast forward a few years and Matt had launched Paper Plane Cocktail Club, a craft cocktail bartending experience for events and weddings. "I contacted super-talented photography team Kimberly and Travis of Calen Rose to set up a surprise that I knew Melissa would love," he explains. "She and Kim had known one another for years, so I told her that I wanted to connect with Kim to create a photo shoot in the Hamptons to get the word out about my business. Melissa, thrilled to be involved in anything shoot-related, loved the idea and couldn't wait to parade around all day in 'costume.'" Unbeknownst to her, however, the shoot was a ruse to capture Matt's planned proposal on film—surrounded by a few close friends and beautiful décor worthy of an intimate wedding.

Event professional Xin Lien of Le Petite Privé designed and coordinated the surprise, which went from inspirational shoot to proposal to engagement party in one day. With such a great team behind him, Matt found the hardest part of the planning process to be "preparing everything behind the scenes and being nonchalant with Melissa," he says. "At one point early on, she jokingly asked me if I was going to propose that day because her best friend Jenna put that little idea in her head! Luckily, I said no, she believed me, and she never thought of it again."

When the day arrived, the Hamptons weather was gorgeous, and the group worked their magic to set a beautiful scene. Melissa enjoyed donning designer clothing that had been selected for her, having her hair and makeup professionally done, and being a central part of the shoot that she believed was meant to support Matt's business. "I am always in awe of the work that Kim and Travis get up to, so I was mostly jazzed to be a part of a shoot with them," she says. "As all the details unfolded, I was along for the ride, because it wasn't about me!" Until it very much was.

Matthew customized the cocktails for the day to put his signature on the proposal. "Melissa originally met me behind the bar, and it was so fun to make cocktails for our friends, bringing everyone together to experience this unforgettable moment," he says. His stunning cocktails added an extra element of cheerfulness to the moment and coordinated perfectly with the event. "I highlighted purples, reds, and greens that would support the incredible vision for the day," he confirms.

Three stunning pairs of Roger Vivier pumps were on-hand for the shoot as well as a set of Numero Ventuno green satin mules. "The shoes were absolutely major!" enthuses Melissa of the options that were presented to her.

Xin is credited with selecting the white Max Mara suit, "but wow, I would have picked it myself!" says Melissa. "I didn't know that I would be proposed to, of course, but it was perfect—bridal without being in a wedding dress. It was stunning and I felt like a rock star." The ivory, crystal-encrusted pumps added sparkle.

Melissa's friends Briar and Taylor participated in the shoot, resplendent in colorful ensembles.

Matt's vibrant blue suit by Zegna made a handsome contrast to Melissa's all-white look. "I felt so confident in it, I am hoping to actually get married in something like it," he says.

An ordinary table was transformed with an exquisite sky-blue covering, coordinating tapers, blush linen napkins, and ombré flatware. Gold-rimmed plates patterned with valley lilies brought a touch of true green to the tableau while chic black seating added some edge.

Menu cards for the faux meal were crafted by Plume Calligraphy on torn-edged, cornflower blue paper with a subtle floral motif.

The floral design reflected the fun, modern aesthetic of the mood board the collaborators created to guide the style of shoot. Victoria Ahn of Designs by Ahn mixed bright pops of color against a palette of dusty shades for a highly impactful display. "It matched the casual elegance of our Hamptons venue perfectly," says Xin.

The prop cake designed by Jess Pickens of Millers and Makers was iced with a marble effect that blended multiple shades of blue. "It was a work of art!" Melissa proclaims.

As the shoot seemingly began to wind down, Matt's plan to propose was set in motion. "I worked out a cue with Kim and Travis so they would know when I was ready," he shares. "I would 'cheers' to them and all the work they and the team had done to make the day possible. After thanking them, Melissa blurted out jokingly, 'But what about our wedding, babe?' She was being funny, of course, but made it very easy for me to drop down on one knee to propose," he says.

Matt kept his words simple and honest, cutting himself off as he started to get choked up. "I said, 'Melissa, you are my best friend. The life that I want to live doesn't exist without you in it. I want to grow old with you. Will you marry me?'" Although it took some convincing, Melissa finally realized Matthew's proposal was real, and she joyfully accepted.

Melissa was delighted by her first look at her ring. "I was head over heels for the ring that Matt chose for me with no help from myself or any friends," she says. "When I asked him to share with me how he chose it, he told me that the teal sapphire reminded him of my eyes. It's perfectly modern with a real vintage feel."

Post-proposal, the couple posed for a few portraits; Melissa, officially a bride-to-be, held a bouquet for good measure.

Melissa couldn't have been more thrilled with the level of forethought and detail that went into the amazing day, including the fact that the mood was so perfectly set. "Spending the day kissing for photographs, holding each other, and being with each other in such a beautiful setting was about as romantic as it sounds," she says. And Matt? He has a few words of advice for other potential proposers. "Be sure it's a good story," he says. "You'll hopefully be telling it for the rest of your life."

Melissa slipped into a burnished vintage gown by Maison Sully as the "shoot" transitioned into a bona fide engagement party.

Photography, Calen Rose
Venue, The Roundtree Amagansett
Event planning and styling, Le Petite Privé
Rentals, The Tabletop Company
Videographer, Miskos Productions
Flowers, Designs by Ahn
Stationery, Plume Calligraphy
Melissa's attire, MaxMara (suit), Maison Sully (dress)
Melissa's hair ornament, Jennifer Behr
Engagement ring, Brilliant Earth
Makeup, Christina Delfino Makeup
Guests' dresses, Maison Sully, Dolce & Gabbana
Shoes, Roger Vivier, Numero Ventuno
Jewelry, A.B. Ellie
Matt's attire, Zegna
Matt's footwear, Salvatore Ferragamo
Cake design, Millers & Makers
Cocktail company, Paper Plane Cocktail Club