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A Memorial White Balloon was Released into the Sky at This Wedding in Rhinebeck

By Shayna Seid | Photography by 

The Day/Ira Lippke

Samantha Greenspan, the senior stylist of private client services at Editorialist YX, and Michael Weiss met through mutual friends. After dating for six years, he proposed over Labor Day Weekend at Auberge du Soleil in Napa Valley.

The pair had just finished playing a round of golf, when Mike told Samantha to get dressed up for lunch. “I decided I was pale and needed to wear a bathing suit under my dress, hoping to sit by the pool after lunch. To avoid making things obvious, he allowed me to arrive to lunch with no makeup, in a dress worn as a cover up over my bathing suit, and not looking my best,” she explains. He had always said that he would propose over the summer, but he waited the entire season and popped the question on the second-to-last day of the trip during a stroll through the sculpture garden after lunch. “He somehow found a way to wedge his phone into a tree and got the whole proposal on film. It was such a happy moment that I will never forget.”

The engaged couple knew they wanted a summer wedding outdoors and were debating between the Hamptons, Westchester, and Upstate New York. “The second we stepped foot on the property at Ankony Carriage House, we knew it was the one. The sprawling hills and greenery were so picturesque. Everything about it felt right,” Samantha says. To help plan their #ForBetterOrForWeiss event, they hired Claudia Hanlin of The Wedding Library.

From the moment the bride-to-be saw the Oscar de la Renta Bridal Spring ’20 collection, she knew the one with the bow in the back was hers— “simple in the front party in the back.” For jewelry, she wore vintage pieces from Fred Leighton, where her engagement ring and their engraved wedding bands were also from. The week of her engagement, Samantha contacted makeup artist Ashlee Glazer, who did her makeup at her sister’s wedding in 2018, and knew she also needed her on her  wedding day.

On August 3, 2019, the original outdoor ceremony overlooking the Hudson had to be tented because of rain. But on the service went, starting with a moment of silence and Mike’s family tradition of releasing a white balloon in memory of his father who had passed away 11 years prior. A vocalist sang Frank Sinatra’s “Fly Me to the Moon,” while the balloon soared, making the moment even more beautiful.

After saying their “I do”s, the newlyweds led the recession with their dog, Olive, who was seated in the front row throughout the whole ceremony. The bride switched to a half-down hairstyle and changed into Miron Crosby western boots for the reception— she was saving them for the after-party, but they practically made more sense after the downpour. “Nothing about our wedding felt country, and that was definitely not the vibe, but my western boots definitely added some flare to my very classic gown,” she says.

Everyone was seated for the delicious dinner, catered by Brandon Scimeca of Hunt & Harvest, and then Samantha’s sister had everyone’s attention for her epic maid of honor speech. “She brought a SoulCycle bike up to Rhinebeck and performed with an audio recording of her voice and the band singing back up. All of our guests were out of their chairs, singing along, and going wild,” the bride explains.

Once everyone was finished laughing, crying, and laugh-crying, dessert was served in the form of a custom wedding cake with seven flavors (one for each layer) by Nine Cakes.

Then, an epic dance party broke out. “Mike and his best friends from business school performed, and our good friend got on stage with the band and sang ‘Shout,’” Samantha remembers.