Tiffany & Greg | Sonoma Surprise Proposal Photography

I always love photographing surprise proposals, but this one was an especially fun treat, as the proposal was for my good friend Tiffany. She has long known that she wanted to marry Greg, and she has long said that she would want me there to photograph the proposal. Tiffany and I both travel a lot, so we actually share a Google calendar to keep track of when we’re both in town. The deception started early, when Greg told me two months beforehand to block off the weekend and pretend I would be in Philadelphia. “Oh, it’s just so much cheaper to fly a whole week before Thanksgiving,” I told Tiffany. Greg and I conspired. He sent me photos of the gorgeous ring that was burning a hole in his pocket. I scouted the winery a couple weeks before the proposal date and illustrated the plan (see awesome photo here). But as the day approached, it was apparent it would be raining, and so we tossed the outdoor plan, and I came up with a whole new plan on the morning of. I conveyed it to Tiffany’s housemate Carrie, who conveyed it to Greg. And it all went beautifully. It was such a joy to be able to witness and capture this moment for Tiffany and Greg and then celebrate with them for the whole day too. I’ll let Tiffany take it from here with her perspective on the day.

From Tiffany: I’ve known since our third date that I wanted to marry Greg. Many dates later, we started talking about marriage, which then turned into a topic that frequently came up with more and more serious consideration, so by this point I knew a proposal was coming, but I didn’t know when. On a rainy Saturday morning, we drove up to Sonoma with my housemates, Carrie and Nick, to spend the day together before the holiday season busyness set in. We picked Jordan Winery to kick off our day (significant because Greg and I had enjoyed their wine during a vacation the month prior) and discovered at arrival that our tour was just going to be the four of us. The tour began as any other winery tour would, and we made our way to the private dining room for Jordan Winery members. The dining room had a stunning view of their grounds & vineyard, but Carrie realized that she left her phone in the car and so headed back with Nick, and our tour guide had something urgent come up and excused herself. I was busy taking photos of the view while Greg started talking about us and our relationship. The moments passed as a blur, but forever in my mind is Greg on one knee proposing that we spend our future together. “Yes, of course!” came naturally and enthusiastically. I then finally realized that Anna was in the room with us (which was crazy because she had told me she was going to be out of town!), and that Carrie and Nick barely left the room. Turns out Greg had been collaborating with Anna, Carrie, and Nick to surprise me!

Wine Country Surprise Proposal | Jordan Winery, Healdsburg

Wine Country Surprise Proposal | Jordan Winery, Healdsburg

Wine Country Surprise Proposal | Jordan Winery, Healdsburg

From Tiffany: I eventually remembered that I was promised a day of wine tasting and we were taken to another room where I was surprised again by our friends who had driven from all around the Bay Area to Sonoma to celebrate with us! It was so fun to see our friends immediately, and even better to hear about all the behind the scenes efforts. 

Wine Country Surprise Proposal | Jordan Winery, Healdsburg Wine Country Surprise Proposal | Jordan Winery, Healdsburg

Wine Country Surprise Proposal | Jordan Winery, Healdsburg

Wine Country Surprise Proposal | Jordan Winery, Healdsburg

Wine Country Surprise Proposal | Jordan Winery, Healdsburg

Nice job on the ring, Greg! I think this rainy marble table perfectly commemorates the rainy day.

Wine Country Surprise Proposal | Jordan Winery, Healdsburg

Wine Country Surprise Proposal | Jordan Winery, Healdsburg Wine Country Surprise Proposal | Jordan Winery, Healdsburg

Wine Country Surprise Proposal | Jordan Winery, Healdsburg Wine Country Surprise Proposal | Jordan Winery, Healdsburg

Wine Country Surprise Proposal | Jordan Winery, Healdsburg Wine Country Surprise Proposal | Jordan Winery, Healdsburg

Wine Country Surprise Proposal | Jordan Winery, Healdsburg Wine Country Surprise Proposal | Jordan Winery, Healdsburg

After a few portraits at Jordan Winery, we headed to lunch at Diavola in Geyserville.

Diavola Pizzeria | Surprise Proposal Photography Diavola Pizzeria | Surprise Proposal Photography

Diavola Pizzeria | Surprise Proposal Photography

Then we had a second wine tasting at Bella, the winery where Tiffany and Greg had their second date.

Bella Winery | Surprise Proposal Engagement Photography Bella Winery | Surprise Proposal Engagement Photography

Bella Winery | Surprise Proposal Engagement Photography Bella Winery | Surprise Proposal Engagement Photography

They taught us that everyone has a dominant nostril, which resulted in some shenanigans.

Bella Winery | Surprise Proposal Engagement Photography

So beautiful.

Bella Winery | Surprise Proposal Engagement Photography

But the surprises weren’t over yet!

From Tiffany: With our hearts warm and spirits high, we all headed back to San Francisco for dinner together to wrap up an amazing day, with Greg assuring me that he had no more surprises. Back in San Francisco, we arrived at Central Kitchen for dinner, and upon walking into the dining room I not only spotted the friends that had been with us all day, but also my parents! I thought that my parents were in Michigan and had even spoken to them both on the phone earlier in the day — but they had flown in just a few hours before specifically for the dinner and to celebrate the engagement (and with this, Greg assured me that there were no more surprises)! The dinner was delightful, and it was a joy to fill my parents in on everything that had happened (but of course, following the day’s trend, they already knew it all thanks to Greg!).

San Francisco Surprise Proposal Engagement Photography | Central

San Francisco Surprise Proposal Engagement Photography | Central

San Francisco Surprise Proposal Engagement Photography | Central

From Tiffany: The day was perfection. Thank you isn’t adequate for the immense gratitude I have for Jordan Winery and Bella Vineyards, for our friends who drove to Sonoma on a rainy day, for my parents who made the long flight for a short visit, and especially for Greg, Carrie, Nick, and Anna who coordinated everything and captured it all. I’m so excited for this next adventure with Greg!

San Francisco Surprise Proposal Engagement Photography | Central

So happy. So happy for the two of you and so happy to have been a part of this special day. Congratulations, Tiffany and Greg!

Anna Wu is a wedding and portrait photographer based in San Francisco. She has become quite adept at hiding in unexpected spots during surprise proposals. Contact her to inquire about your own proposal plans.

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