Molly & Oliver | Golden Gate Bridge Surprise Proposal Photography

Surprise proposals are one of my absolute favorite things to photograph. The excitement! The thoughtful planning! I loved working with Oliver to help him capture his surprise for Molly. I’ll let them tell the story below.

From Oliver: Molly and I met online (this was really my first time ever trying this). After a wonderful first lunch date I was quite intrigued by this person full of energy and a constant smile on her face. We also came to find out pretty quickly that we have a lot in common: big skiers, swimmers, and we both love to spend much time with friends, family and outdoors. So with that we decided to go on another date the next night since I was going to Greece for work the day after. Molly and I are convinced that if that second date had not happened, we probably would not be where we are today. Over the next months our relationship intensified and I came to realize soon that: when you know, you know.

By early December, I had picked out the stone and knew that I was planning on doing this “one knee thing” in San Francisco. I kept the ring hidden in my house until I departed for China on Jan 8. I was going there for work and this ring was burning a hole in my work bag. I can not tell you how often I looked in it, double checked, changed the codes on the safe in the hotel.

From Molly: I’m not great at being surprised, and Oliver isn’t great at keeping secrets. So this proposal took me off guard!

Oliver and I spent the week driving the Pacific Coast Highway from LA to San Francisco. It was a wonderful trip. I’m not typically a car person, but honestly (even though this sounds cheesy), being with Oliver, talking with him and joking around with him was perfect. We knew our game plan once we arrived in San Francisco was to go to a show that his sister had gotten us tickets for as a Christmas present. Oliver had said a couple times that he knew the venue and that there was a little walk we could take if we got to the venue in time. He wouldn’t tell me what the show was because his sister wanted to keep it a surprise.

Once we arrived, we went for the walk that Oliver had been mentioning. We looked at the beautiful view of the Golden Gate Bridge and the many boats on the water (Oliver loves boats, and I like the waves). And that’s when he handed me a card. Words of affirmation are my love language, and he and I do a lot of writing notes to one another– whether he’s going on a business trip and I leave a bunch in his suitcase, or he writes me one and sticks it to my bathroom mirror for me to find in the morning. In fact, every morning of our PCH trip Oliver wrote me a note so when I woke up I could read it and start the day off feeling loved. So when he handed me the note on our walk, that’s when I finally realized that something was up. As I was reading the note, Oliver got down on one knee and asked me the question. I was surprised, and excited, and so thankful for Oliver’s thoughtfulness, his amazing planning and his love for me and for our future. The best part? The words he used to propose are in the card, so we both can remember exactly what he said forever and ever. Well done, Oliver.

Cavallo Point Golden Gate Bridge Surrpise Proposal

Cavallo Point Golden Gate Bridge Surrpise Proposal

Cavallo Point Golden Gate Bridge Surrpise Proposal

Cavallo Point Golden Gate Bridge Surrpise Proposal

Cavallo Point Golden Gate Bridge Surrpise Proposal

Cavallo Point Golden Gate Bridge Surrpise Proposal

Cavallo Point Golden Gate Bridge Surrpise Proposal

Oliver even made sure to thank some of their friends who helped pull off the proposal, and we had Brown Fox Calligraphy help with the thank you cards.

Cavallo Point Golden Gate Bridge Surrpise Proposal

Cavallo Point Golden Gate Bridge Surrpise Proposal

Cavallo Point Golden Gate Bridge Surrpise Proposal

And just because these two are the sweetest, here are a few of Molly’s favorite things about the proposal:

  • The fact that Oliver proposed and I get to spend the rest of our lives together.
  • The fact that he wrote his proposal in a card– I can’t wait to re-read that card over and over again.
  • How much thought he put into the proposal– he hired a photographer!!, he planted the little white lie a month ago as a gift from his sister, the setting of the Golden Gate Bridge was so beautiful, the thank you cards that Oliver created to be sure to thank everyone who was a part of the proposal.

How I should have known what he was up to:

  • The whole week, Oliver was so concerned about the weather! He looked at his phone’s weather app every ten minutes the entire week. Thank goodness it stopped raining for two hours at the exact right time.
  • He wouldn’t let me navigate for him . He’s not great at navigating and driving at the same time so I typically navigate. But he refused to let me do it, because he was texting with Anna throughout the day and I would have seen the texts.

Why I love Oliver:  There are so many reasons to love Oliver, but here are just a few…

  • He is so kind. He always things about others especially about me. He’s one of the kindest people I’ve ever met and I’m excited to watch him spread his kindness to others.
  • He is smart. Oliver challenges me in my thinking, encourages me to keep up even more than I already do with current events, and our conversations are in depth– sometimes to the point of arguing:)
  • He is a little bit dorky. I love that about him. He’s goofy and laughs a lot and doesn’t care what people think about him. It makes me feel comfortable being dorky too.
  • He’s driven. He doesn’t give up on anything. He keeps chugging along with whatever his goals are and it always makes me so proud of him, weather it be training for a race, or getting a new client, or building a relationship– he doesn’t give up.

Cavallo Point Golden Gate Bridge Surrpise Proposal

And Oliver’s favorite parts of the proposal:

  • When she said “yes” ! How can you top that or write anything else?  But sure there were some other parts :
  • Changing in a YMCA to get ready before the proposal: that was just purely hilarious.I remember thinking to myself, once I had the new clothes donned : “wow, I am really doing this, ahhhhhh, I want to call someone right now.”
  • Reading the card with her on the walkway at the breakwater. It was a funny card and interestingly enough I had made a mistake since I had not read the inside. The outside said “surprise” and the inside said something along the lines of happy birthday, which I crossed out and changed to happy engagement. That is when I told her to please look at me and got down on one knee

And a few of Oliver’s favorite things about Molly: She is caring, compassionate, loving (unconditionally, despite whatever difficult situations there are, she has proven this to me a number of times), and kind. And she is always friendly, unselfish, always wanting to help and do what is right, incredibly conversational, and interested in listening to others more than telling her own stories. 

Cavallo Point Golden Gate Bridge Surrpise Proposal

Congratulations, Molly & Oliver!

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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