A Mountaintop Proposal Doesn’t Go as Planned

Everything was perfect—a mountain summit, dramatic clouds, the love of his life. But where was the ring?

There’s a diamond-flanked sapphire ring on top of the Grand Teton. You’ll get $500 and good karma for life if you find it and tell me or Richie. He certainly wasn’t planning for the ring to stay on top of the Grand, nor was I planning to witness an insanely emotional, shocking, and costly moment on one of the world’s most iconic peaks.

It started when my wife, Katie, challenged me to climb the Grand Teton for our one-year anniversary. Neither of us is an experienced climber, especially me. I’m a horseman, conservationist, and filmmaker who’s logged thousands of trail miles, but I trust the two feet underneath me and the four feet of my horses much more than a dangling rope the width of my pinky. But I wasn’t about to say no to my wife wanting to climb the Grand Teton, nor was I surprised.

The climb started with two days of practice with Exum Guides, who slammed home safety and trust in your equipment and partner. The practice mountain was at the base of the Grand Tetons overlooking the beautiful Jenny Lake. We learned the basics of how to climb safely and got to meet our fellow climbers, Richie Jones and Ashley Allen. Richie is the state director of The Nature Conservancy in Delaware and Ashley is an advisor for conservation finance projects in the West. Climbing the Grand has been a 30-year dream for Ashley.

After two days of training we headed up the Grand Teton. Day one was a seven-mile hike with about 5,000 feet (1,524 meters) of elevation gain. The route was insanely beautiful and started in a sage flat, went through a spruce-fir forest, and wound into Garnet Canyon, a high alpine cathedral with twisted white pines, glaciers, lichens, and rocks. Lots of rocks. The Teton Range is the youngest range in the Rocky Mountains and the rocks are honest in the sense they rarely dislocate from the mountain.

We made camp on the lower saddle below the Grand Teton and feasted on freeze-dried meals. Hunger is the best seasoning, so they tasted great. The sunset was ridiculous, and Richie asked me to take some photographs of him and Ashley.

After a few portraits, Richie took me aside and told me he was going to pop the question the very next day on top of the Grand. Ashley had no idea, and he could barely contain his excitement. He asked if I could photograph the proposal, which was an obvious yes! It was Katie’s and my one-year anniversary, so I knew exactly what he was feeling, how important it was for him, and how much he’d treasure the photos. No pressure on me getting the shots right!

None of us slept well, and we got up at 2:45 a.m., slammed some coffee and oatmeal, grabbed our backpacks, and started up the mountain. A 30-minute uphill trudge turned into low-risk but high-consequence steeper slabs, boulder gardens, and mild walls. We roped up a few times for safety and to put the skills we’d been practicing to work. Brief rain and snow showers pelted us with winds going 15 to 40 miles (24 to 64 kilometers) an hour as we worked our way up. It was the first time I had ever been tied to a cold rock wall in the snow and wind while the sun peeked over the horizon and lit the tips of the distant mountains into fiery red cones. Now, I totally get how climbing junkies turn into climbing junkies. It’s awesome.

Katie was ahead of me and belaying my clumsy, non-climbing self up a massive mountain. Although I never actually fell and put my life literally on the line, it was really cool to put so much trust in someone whom I’m married to and love deeply. I tried not to think about the newlywed who shoved her husband off the cliff in Glacier National Park in 2013. (Just kidding, Katie.)

Katie, our guide, Jed, and I made it to the summit about 7:30. It was a feast for the eyes and undoubtedly worth the effort. You could see three states, Yellowstone and Grand Teton National Parks, and the headwaters to the Snake, Green, Gros Ventre, Yellowstone, and Shoshone Rivers. As we soaked in the view, I set up my camera position to photograph Richie’s proposal to Ashley when they reached the summit.

Thirty minutes later they made it to the top. Richie was a nervous, sweaty, sleep-deprived, exhausted mess running on adrenaline and Clif Bars. I winked at him that I was in position. He slipped the ring box out of his backpack and into his pocket.

Meanwhile, Ashley stepped up to the summit, threw her arms out, beamed in happiness, and cried emotional tears that glistened in the morning sun. She was so happy about summiting and had absolutely no idea what was in store for her. She gestured to Richie to join her on the summit rock.

“Now was the time, Richie! Do it!” I thought.

Richie stepped onto the rock and embraced Ashley in a big hug. He whispered in her ear, "We supported each other up this mountain the same way we've supported each other in our lives over the last two years—emotionally, physically, and spiritually—and I want us to do that for the rest of our lives.”

Richie stepped back, took a knee on the summit of the Grand Teton, and looked deep into Ashley’s eyes.

“Will you marry me, Ashley?”

She threw her hands in the air, screamed in obvious delight, and with tears of joy streaming down her face she reached toward the ring box as Richie held it out and opened it.

She gave Richie a puzzled look.

Richie returned the puzzled look. He slowly rotated the box and an expression of utter astonishment swept across his face.

The ring was gone.

No one said a word. Even though Richie was 10 yards (nine meters) away from me, his expression of surprise and horror told the entire story. Time became stagnant, the wind stopped, and there was a three-second pregnant pause before everyone sprang toward them in a valiant effort to find the ring and salvage the Grand proposal.

An incredibly awkward minute passed as all hands on deck scoured the mountaintop for the lost ring. Not a sound was made except the upturning of rocks in search for the ring. Some of those rocks revealed cracks and crevasses that may or may not have had a bottom. When it became apparent that it wasn’t to be found easily, Colby, one of the guides, broke the awkwardness by saying, “Well, what’s the answer?”

“Yes!” Ashley screamed. She embraced Richie and the tense moment immediately turned back into ecstatic happiness. She had a “screw-the-ring-we’re-engaged-and-on-top-of-the-Grand” look on her face, which immediately lifted everyone’s mood.

I looked at Katie, my wife. She was smirking really hard. Someone let out a small chuckle. Somebody else chuckled a little louder. I couldn’t help it, and I burst out laughing. We all burst out laughing, even Richie and Ashley. The absurdity of it all was just too much to contain.

Eventually, as the clouds built along with the risk of an electrical storm, the Exum guides wisely called an end to the search and we began the 10-hour descent.

Richie may have failed at giving Ashley a ring, but it’s possible the mountain gave back more than it swallowed up. Climbing makes you depend on each other to overcome hardships and pull each other’s weight when the other falls, and to face exhaustion, fear, and uncertainty together. Mountains bind people close, leave them with indelible memories, and make them realize that overcoming hardships often depends on solid relationships. Money can’t buy the lessons that mountains freely give, and gifting experiences can be a greater sign of love than the shiniest jewelry.

As Ashley later put it, “We have gracefully accepted the ring's fate as a permanent fixture in the rocks at the top of the majestic Grand, with a reminder always to place spiritual matters above material.”

And in the words of Richie, a self-diagnosed Deadhead, “I showed Ashley a video of the Grateful Dead’s ‘Fire on The Mountain’ right before we began the climb. That energy propelled us through the ascent. It seems fitting, although a bit painful and embarrassing, to leave a sapphire on the mountain.”

That being said, I’m personally giving a $500 reward to the person who finds it and gives it to Richie and Ashley. You should go look for it. Even if you get to the top and don’t find it, the worse thing that can happen is that you climb the Grand Teton.

Follow or contact Ben Masters on Instagram at @BenCMasters.