This Guy Proposed to his Girlfriend 23 Times in a Row – and It Never Got Old.

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How We Met

We met in an airport.  We were both traveling from San Diego to Denver. I was traveling with a good friend of mine from England, Paul, when I noticed her standing in the boarding area at SAN. She was beautiful, I said to Paul. He replied with, she’s out of your league mate. When we landed in DIA and were on our way to the baggage claim, I couldn’t help but ask her about her purple Volcom slippers. They looked extremely warm and comfortable (which I immediately ordered a pair of my own). We chatted about my snowboarding trips and her horse events. She was a trick rider who cold jump horses through rings of fire, ride two horses at one,and just happened to play teh piano, violin, and harp. I had been waiting till friends flew in from other flights. When they arrived, Cubrina and I said our goodbyes then parted ways. Outside of the airport, I asked my friends to wait as I ran back in to ask for her phone number. We texted and chatted in the following days, and two weeks later we were snowboarding in Vail :)  The rest is history.

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How He Asked

We were taking a hiking trip to Oahu. We had hiked the Big Island in November and are into traveling and hiking to get cool pics, drone footage and take in the moments of being immersed in nature. We had been together just over 2 years. I had a ring made and selected a stone 4 weeks before our trip, and just happened to pick it up a few days before we flew to Hawaii. I wanted to propose on the Haiku stairs, or stairway to heaven, on Oahu. But every morning we went, it was raining, so we’d venture of to a different part of the island to hike.

We were at a lighthouse hike and there was a guy who had a pool skimmer and was trying to retrieve his crashed drone on the cliff side. It was about 40 ft down from safely, and then it was probably another 1500 ft straight down into a set of tide pools. While helping this guy, a strong wind came and almost blew me off the edge of the cliff. When I got back to a safe place, I asked that guy to hold my go pro, then I proposed right then and there. I remember thinking that if I had fallen, I’d never have the chance to tell Cubrina how much she meant to me. It the first proposal in the video.

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While walking down the mountain, the other side had another amazing view. So, I asked that guy to film me proposing again. As the week went on, I proposed over and over, a total of 23 times. We filmed them all and on the fight home decided to see if we could splice them all together. We even flew to Kauai to take a helicopter tour of the island and tube down an old irrigation ditch from a sugar cane field from a time going by long ago.

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It never got easier, proposal after proposal. I was nervous every single time, and she cried for the first 10 times or so, maybe more. I called it, ‘exposure therapy.’ I wanted to make this video so we would have it to watch over and over for the rest of our lives. And to set the bar for any guys that may want to propose to any future daughters we may have.

Plus, Cubrina isn’t any ordinary woman. She jumps horses through rings of fire, can ride standing on 2 horses simultaneously, plays the violin, piano and harp… plus she has her own equine thermography service (delmarir.com). She’s a down to earth Superwoman. On top if all that, she’s only 23. Therefore, she shouldn’t have any ordinary proposal, she deserved 23 amazing proposals.

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I submitted this to show others that they don’t have to follow the rules of a single proposal. You can make it anything you want to make it.

Our Video

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Special Thanks

Nicholas Friedman