A Private Estate Surprise Wedding

J and C met in college and after being together for 8 years, J proposed on a cross country road trip to New York. While stopping for a visit in Montauk, J set up dinner at a restaurant and while sitting on the beach, surrounded by rose petals and champagne, J proposed to C with a personalized scrapbook of all their photos together with the last page saying ,”We have had so many amazing adventures together and I can’t wait to do more, do you want to do life together?”

J and C knew they didn’t want a traditional wedding and wanted the home they purchased together to be a part of their special day. They started playing around with the idea of having a surprise wedding but they were not sure how to pull it off or where to even start. After being engaged for a year, they reached out to Pocketful of Plans and asked about doing a surprise wedding and on a short timeline, they already had spent a year engaged they didn’t want to spend another 10+ months planning.

I had the honor of working with the bride’s sister for her wedding in 2021, and knew the couple already and was thrilled to plan their surprise wedding. The mantra for this entire planning process was “ If it’s meant to be, it will be and we will find a way.” We all really embraced that and found a way to make a surprise estate wedding happen.

The couple’s home is a traditional home you see a lot of in San Francisco, its narrow, tall, and full of old charms and quirks. And they wanted to keep true to that style, but also make it feel like a colorful garden party. Since we were inviting their guests under the guise of a engagement/house warming party we used a lot of colors and textures in the florals as well as great lighting to make their vision come to life. We also wanted to be true to the laid back SF style by keeping the flowers and rentals feeling earthy and organic.

It goes without saying that pulling off a surprise estate wedding comes with some challenges. The biggest challenge was turning the garage into a beautiful and intimate dining space for the reception, and keeping that hidden as guests arrived. Small city homes are not made to host 50 ppl so we had to get really creative. A lot of time, thought and in-person visits went into making this work and the vendor team came together to make it happen flawlessly and within 90 days start to finish.

The garage transformation took several months starting with filling concrete, checking electrical, moving things and cleaning. Installing the coverings took 2 days alone. Even though it was an intimate 50 person wedding, it was a very involved process. The couple also did a pretty extensive remodel to the back yard in the 3 months of planning to make enough space to have the intimate ceremony. We knew the space would be tight but it also ultimately felt magical, cozy and incredibly personal.

The couple kept the wedding small and intimate only having those that are incredibly important to them attend. J has a small family, and supportive community that helped raise him after his mom passed. A lot of the people attending the wedding have been his friends since preschool.

No one knew they were attending a wedding except for the parents and the bride’s sister. The guests were told that they were actually attending the couples engagement party. How we pulled it off: about half way through the cocktail party I pulled the couple away. We went inside and Caroline immediately started getting into her gown with the help of her mom. After she was mostly ready, Jared went outside and made an informal toast and spilled the secret. Seeing the surprised looks on their friends and families faces was the most memorable part of the day. J’s grandma was so surprised and had the sweetest reaction to all of it, including yelling in shock and tears. Some people suspected that there was something more to the garden party but most everyone was incredibly surprised and honored to be a part of their day knowing that they were truly the most important people to the couple.

In order to pull off this sort of wedding were you can’t actually tell people it is a wedding or to expect dinner you take a leap of faith. We planned a really beautiful family style meal that would work in the small space but also was full of elevated and local touches. The food was hugely important to the couple and the team at Betty Zlatchin Catering went above and beyond to work in a tiny space and still produce an exceptional meal. One thing that C&J completely trusted me on was the importance of a solid vendor team that could pull off tiny miracles to do all this without giving away the surprise. The end result was not only a fun surprise but ultimately a beautiful, memorable experience that will stay with all of them forever.

On the most perfect, sunny day in July, we pulled off an intimate and fun surprise wedding. The vibe was so excited and the surprise element was incredible and one I won’t soon forget. While the wedding was different and a surprise we all agreed after the fact that there was nothing lacking from this day that can be found in a traditional wedding.