New York City-based documentary filmmakers Holly Siegel and Tom Denison first met at work, where they sat about ten feet away from each other every day.“We had assigned seating that had us back-to-back all day long,” recalls Tom. “That sparked a running conversation that would begin in the morning and lasted until we packed up at night.”
The two discussed everything except for their dating life. “I used to joke to my friends that despite spending all of my time with him, and having fully developed a crush, I still didn’t even know if he had a girlfriend,” laughs Holly.
Finally, one night in January, he invited her to meet him at a bar near her old apartment. “It was one of those beautiful New York snow storms and the entire city was quiet and freshly covered with snow,” she remembers. “At some point, I realized that deep in my purse I had a box of sparklers Tom had given me months ago after a Fourth of July vacation, and we decided to go down the street to my roof and light them. The rest is history!”
The two had been dating for four years when Tom proposed. It was a Sunday evening in mid-December and because they were planning on traveling for the holidays, they decided to celebrate Christmas and Hanukkah early. They lit all of the candles on the menorah and placed all of their gifts under the tree. After exchanging presents, Tom went over to his closet and pulled out a bouquet of flowers. “He said he had one additional thing,” remembers Holly. “And, of course it was the best of all! I was stunned and overjoyed. We both just stood on our living room floor with so much emotion that we were crying and laughing.” They then went to their favorite neighborhood restaurant where Tom had arranged for them to be greeted with champagne and seated at their favorite table.
About a month after they got engaged, they started planning and discussed a lot of possibilities, but ultimately settled on Napa; a place close to Holly’s hometown and where they’ve spent a lot of time together. They spent a day with Holly’s parents and their wedding planner Laurie Aarons visiting venues and decided on a beautiful private home overlooking the valley.
“We wanted the wedding to be intimate and have the same feeling as one of the many dinners Tom and I have hosted at our place—not overly fussy or overdesigned,” explains Holly. “Overall, I was drawn to the climbing roses that grow throughout the Napa region. Our amazing florist, Mindy Rice, quickly jumped on-board with this idea and sketched a tent that would be enclosed and filled with rose-covered trellises. It was straight out of my dreams!”
One week before their October wedding, Holly traveled home to San Francisco. “On the first night, my dad and I both woke up to the smell of fire and turned on the TV to learn that wildfires were spreading throughout Napa,” says Holly. “Of course, it wouldn’t become apparent until later in the week how devastating the fires would be to this region, a place that’s so close to our hearts.”
They were optimistic the fires would improve the following day. “[But,] on Monday, it was only getting scarier and more destructive,” remembers Holly. “It was heartbreaking to watch. Earlier that day, my mom mentioned a message she had received from a dear family friend offering up her home in Atherton. We were so touched by her generosity and what an incredible gesture this was. That afternoon, we decided to relocate our wedding and felt very lucky to have such an incredible alternative.”
They quickly visited Atherton, and their family friend welcomed them with open arms and guided them around the property in search of the perfect nook for the ceremony. “Thinking back to those few days of relocating is a total blur—so much happened so fast,” says Holly. “During this time, my mom was an endless source of strength, creativity, and laughs.”
Within days of the change, the entire first floor of Holly’s childhood home in San Francisco was cleared out and set up for the rehearsal dinner and welcome party. “We had fun with Mindy digging through my mom’s vintage linen collection for the table settings,” says Holly. “Merrell, one of my bridesmaids and Tom’s old friend, painted the most adorable menus for everyone in just a few days! Jesse, another one of my bridesmaids, owns the most delicious pie shop in San Francisco, Mission Pie, and they catered dessert.”
The actual rehearsal took place on the stoop and spilled onto the street, followed by a dinner in the living room. The welcome party spread throughout the home and up to our roof deck. “It was the best way to kick off the weekend—at home, warm, and packed full with love,” says Holly.
Amidst the chaos of moving the wedding, persistent messages from our families and friends kept reminding Holly and Tom of how excited everyone was to be with them and how amazing it would be no matter what. “There was a clear moment during that whirlwind when I realized all that mattered was that I was going to marry Tom, surrounded by everyone we cared about deeply, and everything else was just the icing on top,” says the bride.
The bride’s stellar wedding weekend wardrobe was part of that proverbial icing on top. She saw her Oscar de la Renta dress online, and it instantly caught her eye. “My mom came to New York, and it was the first dress I tried on and after a very long day of shopping, it remained my favorite,” says Holly. Around that same time, Holly’s grandfather presented her with her grandmother’s wedding dress. She had boxed it up to share with Holly one day.
“It was an absolutely perfect gown, equally as spectacular as the stories I heard growing up of their garden wedding in 1950,” says Holly. “I knew I wanted to incorporate it somehow so we decided that I would use the lace to create a veil.” Holly, however, had no idea how to go about doing this. Thankfully, she was connected with wedding stylist Cynthia Smith of Cynthia Cook Brides, and she had all of the answers. “Cynthia introduced me to the most talented tailor/dressmaker, Bill Bull, who also worked with me on all of my dresses ensuring they fit perfectly,” explains Holly. “We had so much fun crafting the veil from my Grannie Annie’s dress, and it was such a sentimental process. There was a moment, just after I got situated under the chuppa, when the wind blew and swept my veil up in the air. We all felt her presence throughout the ceremony, and I am forever grateful to have a piece of my grandmother’s dress that I can continue to pass down.”
Throughout the wedding planning process, Holly felt especially connected to the women in her family. “[Because of this,] my mom and I decided that all the jewelry I wore would be family heirlooms,” she explains. “We chose a pair of delicate diamond earrings that belonged to her mother, and on our wedding day, she passed them down to me.”
The morning of the wedding, Holly and her bridesmaids got dressed at home. Over the summer, her mother had purchased all of the girls vintage linen dresses from the market in Provence to get ready in. They did hair and makeup in her childhood room and her parents’ bedroom. “It was such a comfortable and relaxing way to start the day,” she notes.
That afternoon, Holly and Tom were married by her family Rabbi. “We met with him several times, independently and together, to discuss our relationship, marriage, and the ceremony,” says Holly. “This was the most enjoyable and grounding part of wedding planning.” There was a curving aisle leading up to the chuppa. “The second my dad and I turned to go down it, and I saw Tom up there I felt pure happiness,” says Holly. “I loved walking down the aisle with my dad—there was something about participating in that tradition that I adored, and it felt even more special to be wearing a piece of his beloved mother’s dress.”
Tom was dashing in a deep navy Thom Sweeney suit. “It fit him perfectly,” says Holly. “He looked so handsome!” Each bridesmaid picked her own dress with Cynthia helping to curate by pulling inspiration and possible choices. “I imagined it as soft tones and flowing materials,” says Holly. “And, my best friend actually wore the same dress I wore as a bridesmaid at her wedding!” Mindy created all of the bouquets with the dresses in mind.
“Once I was standing up there with Tom, I didn’t look anywhere but at him,” remembers Holly. “I didn’t even notice the spectacular chuppa until nearly five minutes in. After such a crazy and unpredictable week, it felt as if time had suddenly stopped, and we were able to be fully in that moment. It was entirely overwhelming but unforgettable.”
The two each wrote a bit about each other in advance of the ceremony, and their Rabbi shared their thoughts out loud. “I loved hearing what he said and remember it exactly,” says Holly. “While planning the wedding, we thought a lot about which Jewish traditions we wanted to incorporate, especially since Tom is not Jewish. I felt strongly about having a chuppa because, as somebody who cherishes ‘home,’ the meaning of it has always resonated with me. I loved how our Rabbi articulated this on our wedding day:”
“We begin married life under the chuppa because it is a fragile impermanent structure that is only the promise of permanence. It is a reminder that the strength of a home comes from the people who inhabit it, and who love and choose to be together. The chuppa does not keep out inclement weather or avert catastrophe. It serves as a reminder that your anchor and strength will come from holding onto each other’s hands as you do now. It is a reminder that marriage involves a great deal of hard work, of open communication and sharing and building, and always with good humor and an ability to laugh at yourselves.”
“The ceremony was a moment of incredible happiness,” remembers Tom. “As we held hands on the altar, with our parents behind us and all our family and friends looking on, I felt so excited about our future together.”
Afterwards, guests gathered in the reception tent. “The first thing I noticed when I stepped into the tent was how heavenly it smelled!” remembers Holly. “I still cannot get over how Mindy Rice transformed that space. Our incredible caterer, Paula Le Duc, was able to keep our original menu despite the location change, and we served a salad along with the choice of steak or fish. The endlessly talented Stephanie Fishwick designed our stunning menus, and the florals complemented it all in every way.”
During dinner Holly’s parents, and three of the couple’s, dearest friends gave toasts. “Each of them was so heartfelt, funny, and loving,” says the bride. “To this day one of the first things our family and friends bring up about our wedding are those speeches.”
The dancing started after dinner. “Our band, James Gang, was fantastic and the dance floor was fully packed through the night. I have never danced that much in my life, and when we finally stopped, I couldn’t believe it was all over!”
After we cut the cake, the newlyweds gave a short speech together. “It was such an amazing feeling to look out at everyone in that moment,” remembers Holly. “There are no words that can describe seeing all of the people you love in one place! Sweeter than the cake itself, was Tom’s speech. He had written something on paper but midway decided to speak directly to me instead. It was such an overwhelming feeling of emotion—complete and pure happiness. Because of the circumstances of the week prior, I think there was an extra feeling of gratitude that filled our wedding and you could feel that energy the entire time,” says Holly. “I would have happily stopped time and moved into that tent forever.”
