Surprise Proposal at Powell Butte: Ben & Lyndsey’s Story

I’ve worked with Lyndsey at my day job for just over a year. She and her now-fiancé, Ben, came to one of my fall mini sessions in October, where we took some sweet couples photos.

Fast forward a few months—and even though they were already planning their wedding for August—Ben still hadn’t officially proposed yet! One day at work, I casually mentioned to Lyndsey, “If you want proposal photos, just have Ben text me.”

Spoiler alert: he did.

Planning the Perfect Surprise

A day or two later, Ben reached out on Instagram. He wanted to pop the question soon, and we needed a location that felt meaningful but also wouldn’t be a muddy Oregon mess in late February.

His top pick? Powell Butte, which was perfect. It’s a place Lyndsey runs frequently and holds a lot of sentimental value.

His backup was Angel’s Rest, but I quickly vetoed that—because no one wants to be sweaty and windblown mid-proposal.

How We Pulled It Off

Lyndsey had no idea. Her sister planned a little “spa day” with pedicures and manicures, then casually suggested they stop at Powell Butte on the way home to “scope out a future proposal spot.”

Meanwhile, Ben and I were hiding behind a tree near the trail entrance.

That is… until Lyndsey spotted Ben’s car in the parking lot and instantly knew something was up. (Busted.)

The Proposal

We timed it just right—Ben and I positioned ourselves so that Mt. Hood was in the background, and let Lyndsey and her sister walk past us to get to the perfect spot.

The weather was unreal for February—sunny, clear, and warm. The moment he dropped to one knee, she was glowing. And yes, she said yes!

Afterward, we asked if she was surprised. Her answer?
“I saw Ben’s car and figured it out!”

From Proposal to Engagement Session

After the big moment, we hiked up to the summit and took some engagement photos. First, we wandered through a quiet grove of trees, then made our way to the western viewpoint to soak in the full Mt. Hood view.

One of my favorite moments was toward the end of the session. I gave them one of my go-to prompts:

“Pretend I’m not even here.”

Lyndsey and Ben slow danced in the grass as a newly engaged couple, and I just stood back and captured the sweetness of it all.

Why This Session Meant So Much

This was my first surprise proposal session—and I got to do it for a friend. As of writing this in June 2025, I’ve now photographed Lyndsey three times: their fall mini, her proposal, and branding photos for her fitness business.

Moments like this remind me why I do what I do. I love photographing real life—big and small. The joy, the nerves, the laughter, the love.

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Ready to Plan Your Own Proposal?

If you’re planning a proposal, engagement session, or just want to document this season together—I’d love to help you capture it.

📸 I’m offering $75 off all couples sessions through September!