Surprise Marriage Proposal and Engagement Session at a Scenic Overlook in Breckenridge, Colorado
Every once in a while, a proposal hits a little closer to home — literally. This one was for my cousin Nolan and his now-fiancée, Audrey. He asked me to fly in from San Diego to photograph his surprise proposal during their one-year anniversary trip to Breckenridge, Colorado. The answer was an easy yes. Family, the mountains, and a love story? My favorite!
I’ve known Nolan for most of my life, so being behind the camera for this moment felt surreal. We grew up jumping on the trampoline in my aunt’s backyard, running around at family reunions in places like Yellowstone and Sequoia, playing Sonic the Hedgehog on GameCube, and having nerf wars in the basement trying to spot his twin, Ben, cheating for the hundredth time. We went through hell and back when he and Ben were in a car accident. Our whole world shattered when Ben didn’t make it.
Nolan is one of the strongest people I’ve ever met. He healed from his injuries, graduated college, trained for an Ironman in Ben’s honor and has since traveled all over the world to compete in a dozen more. To see Nolan in love, grinning ear to ear, and planning a proposal for the woman who brings out his best self brought out the sappy cheeseball in me.
Behind the Scenes of a Surprise Mountain Proposal
The day of the proposal, we planned to meet at a scenic overlook in Breckenridge that could easily double as a postcard backdrop—mountains, evergreens, and that crisp Colorado air that smelled like pine and nostalgia. I showed up early, bundled in a scarf and hat to disguise myself (very stealth), and waited for their arrival. The overlook was perfect and intimate until Nolan and Audrey parked and suddenly, half the town showed up, too!
They took in the views while Nolan stalled like a pro while waiting for the crowd to disperse. Finally, the moment arrived. He got down on one knee, and Audrey’s reaction was everything. Shocked, teary, and saying “yes” over and over again. I finally revealed myself, tried to hold back tears, and hugged them both so tight. After the ring was on and the moment sunk in, we wandered around the overlook for a mini engagement session. We laughed, climbed the rocks, and enjoyed the fall colors.
The night before, my aunt organized a dinner at her house with more of our family. we all went around the table saying one word to describe Audrey. Bubbly, kind, effervescent — basically a ray of sunshine. Nolan has always been more on the quiet side, the thoughtful one who observes and saves his words for when they really count, but Audrey brings him out of his shell. Together, they joke around, soak up all of life’s experiences, and support each other’s endeavors. She’s officially part of our wild, loving family now, and I couldn’t be happier about it.
The Fastest Minute of Your Life
Proposals happen fast. There’s no script, no redo, and that’s exactly what makes them beautiful. My responsibility as an engagement photographer is to make sure you get to relive it — the nerves, the surprise, the joy. Whether we’re planning a proposal in the mountains of Colorado or along the cliffs of San Diego at sunset, I am here to help with everything — location scouting, timing, and how to make it all feel natural and true to you and your partner.
Watching these two together reminded me why I do what I do. Whether it’s photographing proposals in Colorado or sunset sessions on the cliffs in San Diego, it’s about documenting that in-between space—the moment when life changes and you realize you’ll want to remember it forever.Nolan and Audrey’s proposal is one I’ll hold close for a long time. It’s not just because they’re family, but because it is a once in a lifetime moment that I get to not only witness, but capture for them to remember forever.
Reach out here and I will document your own love story.
Click here to read about Ben and learn more about our family’s annual Benjamin Ollada Foundation Golf Tournament. We raise funds for a scholarship fund granted to deserving engineering students at the University of Colorado at Boulder! Cool, huh?
