Brian and Cailey

How We Met

Brian and I met in seventh grade. We had a first period English class together, and I had the biggest crush on him… I was so shy that he doesn’t remember meeting me until eighth grade. Through junior high and high school we became close friends, spending evenings playing ping pong with friends in my parents’ garage or sitting for hours on end at Dairy Queen (Brian’s first job) while Brian worked.

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All the while I still didn’t have the nerve to make a move. Finally, Brian kissed me, we had an accidental first date when a friend backed out of plans to see a movie at the last minute (Brian swears that wasn’t planned!), and we started dating during our senior year of high school in April 2008.

How He Asked

Brian and I celebrated our ten year anniversary in April 2018, but life and work made it difficult to get away for a celebration until late June. We planned a weekend of wine tasting and relaxing in Yountville, and Brian took it upon himself to make some reservations throughout the weekend as a surprise for me. On the afternoon of Friday, June 29th, after a relaxing morning of sipping sparkling wines while overlooking beautiful vineyards, Brian and I got ready for his afternoon of “surprises”. He told me we had dinner reservations at 8:00 pm at a nice place, so we got dressed up and made our way to our first surprise location – Castello di Amorosa Winery.

Where to Propose in Castello di Amorosa

The winery is modeled after authentic Tuscan castles and is absolutely stunning. While waiting for our 4:00 pm tour to start, Brian told me there would be another surprise location between the winery and dinner (he knew I was a bit suspicious, so he wanted to throw me off – and throw me off he did!). We spent the afternoon on a private tour exploring the castle and its gorgeous wine caves, enjoying barrel tastings, and finishing off with a private tasting of the winery’s best offerings.

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By the time the tour and tasting were done, it was just after 6:00 pm and the castle had closed, so it felt as though we were the only people left on the grounds. Brian casually told me we should get ready to go to our next location. I assumed he planned to pop the question at this mysterious second location, so I freshened up and got ready to go. We made our way out the giant castle door and across the drawbridge when I noticed Brian had stopped walking. I turned and saw tears in his eyes and quickly realized there was no second location. At that point we were both emotional – I pulled him in for a quick hug and told him how much I loved him before he got down on one knee and asked me to marry him. Of course, I said yes!

Brian's Proposal in Castello di Amorosa

Brian planned the most incredible proposal, it was more perfect than I ever could have dreamed. I can’t believe I get to spend the rest of my life with my best friend, and I can’t wait until the day we say “I do”.

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Special Thanks

Lynn Lewis
Photographer