
Photo by TRK Photography
Karen and David met in July 2011 on a party bus trolley while celebrating a mutual friend’s birthday. When Karen put David’s number into her phone, she didn’t know his last name, so she stored it as “David Trolley”—which is still his contact name a full decade later. When David ultimately decided it was time to propose, he made an intricate decoy plan over Thanksgiving weekend, which started with Karen heading to Mexico City to spend time with her family and David traveling to Chicago to celebrate with his. David wanted to fly directly to Mexico City from Chicago to surprise Karen, but when he realized he left his passport at home, he had to fly back to San Francisco, grab his passport, and head directly to the airport to catch a red eye flight to Mexico City. There, Karen’s family was keeping her distracted at Chapultepec Park when all of a sudden, “I Choose You” by Sara Bareilles started playing. She turned around to find David with two bouquets of flowers and a ring.
After considering an elopement, Karen and David met with Jana from Tobey Events to discuss how they could transform the patio of the private condominium building where they lived in Naples, Florida, before moving together to San Francisco. “We decided to get married at the building that we spent so much time together building memories in,” Karen says. The couple invited 100 guests to an ethereal beach ceremony on December 11, 2021, followed by a candlelit reception under a tent of lights. Check out the cool ombré effect of the couple’s centerpieces in these photos by Tiffany Kelly of TRK Photography.
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Photo by TRK Photography
The couple’s invitation suite from Luster Designs featured modern fonts in a soft shade of purple inspired by some of the wedding day’s flowers. The invitation read “At Last” as a nod to the couple’s 10-year-long relationship.
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Photo by TRK Photography
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Photo by TRK Photography
Karen didn’t go through the process of trying on several wedding dresses and tossing and turning over whether she found the one. Instead, her ivory Pronovias gown, complete with a halter neckline, was gifted to her! When one of her sister’s friends decided to have a smaller ceremony during the pandemic, she no longer needed her wedding dress. “We made a joke that the friend should send itto me... and she did...and it fit perfectly!” Karen says. “It was serendipity and almost as if this dress was specifically designed just for me.”
The gown also solidified their big-day plans: Before she was given the dress, Karen and David were seriously thinking about eloping. When it landed in Karen’s hands, though, the couple decided to move forward with wedding planning.
Karen accessorized with her mother’s bracelet as her something borrowed and Loeffler Randall shoes. She wanted her beauty look to complement her green eyes and natural freckles and chose an updo with pearl embellishments to show off her drop earrings.
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Photo by TRK Photography
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Photo by TRK Photography
Karen and David decided to have a first look to save some time and enjoy their cocktail hour with their guests. “It felt totally natural,” Karen says. “Even being surrounded by photographers and videographers, we felt like we were able to enjoy each other's company.”
David’s wedding-day look was a floral print Indochino suit, which he accessorized with his late grandfather’s cufflinks. He spent the morning on the beach with his friends (wearing sunscreen, of course!) while Karen got ready.
Karen’s bouquet from Tom Trovato consisted of lavender larkspur, blue clematis, fresh lavender, lavender stock, tweedie, blue thistle, dusty miller, succulents, and silver dollar eucalyptus.
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Photo by TRK Photography
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Photo by TRK Photography
The couple’s ceremony took place on the beach, where a floral chuppah, also by Tom Trovato, took center stage. The chuppah was embellished with greenery, textured bunny tails, and flowers in shades of purple, blue, and aqua. “Favorite moment was stepping out on the beach and seeing how spectacular the chuppah was,” Karen says. Each row of the aisle was decorated with a matching floral arrangement.
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Photo by TRK Photography
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Photo by TRK Photography
As guests were seated for the ceremony, a violin and guitar duo played tropical tunes to set the mood. The musicians played “I Won’t Give Up” by Jason Mraz for David’s walk down the aisle before Karen processed in with her parents to “Cherry Wine” by Hozier. Karen’s aunt officiated their ceremony, for which wrote their own vows; Karen was sure to include the fact that David is still “David Trolley” in her phone. They rejoiced back down the aisle to Coldplay’s “A Sky Full of Stars.”

Photo by TRK Photography

Photo by TRK Photography

Photo by TRK Photography

Photo by TRK Photography
The couple’s reception took place on their condo building’s patio, which was transformed with a canopy of string lights and oversized king’s tables draped in velvet linens. Guests accessed the reception area through a tunnel of lights from the beach. The couple’s planner brought in two black bars and set up the couple’s sweetheart table in front of a black arched wall and neon sign.
Tablescape décor included a mix of bone and black taper candles in brass candleholders. The place settings featured black plates, gold flatware, and napkins, plus menus that were matched to the colors of the flowers. “The swatches had to be taken to a paint specialist and matched exactly and then all of the flowers had to be spray painted to get the ombré effect we were looking for,” the bride says.

Photo by TRK Photography

Photo by TRK Photography
For dinner, Karen and David served their a four-course meal paired with favorite wine from their go-to winery, Matthiasson Wines in Napa Valley. Appetizers included sweet and spicy ahi tuna cones, petit jumbo lump crab cakes, short rib gougeres, and wild mushroom and caramelized onion with melted brie grazing boards. Guests enjoyed a grilled chicory salad followed by their choice of a braised short rib entree or pan seared snapper dish. “We also are obsessed with Norman Love’s white chocolate raspberry cake and their cookies, so we served both,” Karen says. Along with their wedding cake, guests enjoyed peanut butter cookies for dessert.

Photo by TRK Photography

Photo by TRK Photography

Photo by TRK Photography
The reception kicked off with ambient piano music before the entertainment switched to a hybrid of a band and a DJ. “We wanted to have original songs with electric violin, saxophone, and full percussion flair,” Karen says. “The electric violinist and saxophone player hopped off the stage and danced with the guests to keep the dance floor moving and grooving all night.”
The couple shared their first dance to “I Choose You” by Sara Bareilles, the song they got engaged to. They ended the night with “Wannabe” by the Spice Girls—and then Karen and David jetted off to spend 10 days exploring in Antarctica. To couples planning a wedding, Karen and David recommend hiring a wedding planner. “Specifically Tobey Events, who was amazing!” they say.
Wedding Team
Photography Tiffany Kelly of TRK Photography
Videography New Rez Media
Wedding Planning and Event Design Tobey Events
Invitations and Day-of Paper Products Luster Designs
Flowers Tom Trovato
Bride’s Hair and Makeup Simply Sapphire Beauty
Catering Crave Culinaire
Wine Matthiasson Wines
Rentals Plithos; Exclusive Affairs Party Rentals; Party Time Rentals and Special Events
Music Jade Strings
Lighting Opulent Lighting & Design