How We Met
Katie and I both attended the same university in California but never actually met there. I graduated one year earlier, then moved back home to Hawaii to launch my company. During her senior year, Katie and her group of friends visited Hawaii for Spring Break. A mutual friend asked if I would show them around for a true local experience. I gladly obliged, and I’m so glad I did! I met up with Katie and seven others and led them on a sunrise hike and other activities around the island. It was the dawn of our friendship and journey together.
After that trip, Katie went back to school in California. We stayed in touch and continued growing our friendship, including Skype conversations lasting up to nine hours! Several months later, I boldly invited her to return to Hawaii to spend more time together and see if we could be more than just friends. She accepted and three days into the trip, we decided to make a go for it and committed to a long distance relationship. That was one of the most incredible and romantic weeks of my life and the blossoming of our love.
Over the next five years, we built our long-distance relationship Facetime call by Facetime call, text by text. Then it was “like Christmas” several times a year whenever we reunited! No doubt we faced struggles (just like any couple does!), but especially when going for months apart without seeing each other (we calculated that in our nearly five years spent together, just 14% was in-person). Most of all, we always put gratitude at our core and stayed strong knowing we were setting the invaluable foundation to a relationship that could last a lifetime.
how they asked
I wanted to “pop the question” to Katie in an epically awesome, uniquely creative, and relevant-to-our-relationship way. Words just wouldn’t suffice, so I thought maybe action in the form of an elaborately planned proposal would get me just a little closer to expressing how much I love her.
I gathered inspiration and ideas by watching YouTube proposal videos and reading stories here on how they asked. After brainstorming a long list of possibilities, I decided on a surprise proposal adventure, up a mountain in Hawaii, at sunset supported by family and friends.
The entrepreneur in me went all out in the prep for this “most important project of my life.” I put together an extensive project plan, then recruited a core team of people, from professional video/photographers, and two friends who I gave the roles of “Uber Driver” and “Inception Consultant.” We met almost weekly to plan and figure out logistics.
During the two months of proposal preparation, Sara Bareilles’ “I Choose You” played constantly in my head. No joke… I listened to that song every night before bed just imagining the proposal moment. Working intense 60+ hour weeks while also planning this project, the song helped calm my nerves and kept me motivated – positive visualization!
Knowing Katie is a smart cookie (I failed at throwing a surprise party for her before), I knew I would need to execute every detail perfectly to pull off this surprise. So, one week before Katie’s trip to Hawaii, the inception process began: I told her I needed to attend an all-afternoon professional retreat for a nonprofit I volunteer for (allowing me to break away from Katie and coordinate the proposal setup). I also made up plans for a “very special dinner reservation” at a fancy restaurant that evening after the “retreat”.
With the “dinner reservations” and “retreat” scheduled back-to-back, I told Katie I would have to arrange for Scott, my Uber driving friend, to pick her up to meet me at the restaurant. Luckily, she bought the whole thing!
On the day of the proposal, Katie and I enjoyed a sunrise hike at the Makapu’u Lighthouse Trail (where we first met!), enjoyed a delicious breakfast, and relaxed at the beach. The perfect day was unfolding.
Then, I left for my fake retreat while Katie kept busy at home. Over the next couple of hours, I was able to set up the proposal site, coordinate everyone involved, record the surprise message video, and change into my suit.
Scott picked Katie up from the house in his car rigged with GoPros (which he told Katie was for a new Uber security policy). Midway into the drive towards the restaurant, Scott told her, “Sorry, I need to use the bathroom” then pulled into a public beach park. There, he changed from beach clothes into a suit and returned to a confused and surprised Katie.
He handed Katie a red rose and an iPad with my surprise video message revealing what was really happening, then proceeded to drive her up a stunning mountain.
At four stations along the mountain ascent, close friends and family patiently waited to surprise Katie. At each station, there was a tablet with pre-recorded greetings from dozens more friends and family from across the globe (everywhere from Thailand, Taiwan, Japan, California, Minnesota, Oklahoma, New York, to Paris!) and a video of me narrating from a handwritten journal sharing our relationship journey. By flashing up photo posters, friends and family helped to enliven the story as it was told.
After ascending up the entire mountain and strolling up a garden pathway, Katie finally reunited with me at the top. I gave my proposal speech (fortunately she wasn’t bawling as I had imagined but instead was so incredibly at peace and happy, otherwise I wouldn’t have been able to hold it together to remember the words!), got down on one knee, and asked the big question.
Katie said “Yes, definitely!” We then shared our first dance as an engaged couple to “I Choose You” while taking in a picturesque Hawaiian sunset.
Afterwards, friends and family rushed in to join in celebration!
Everything was perfect on what I truly consider the best day of my life.
Katie and I are so humbled by and appreciative of all the overwhelming care and kindness surrounding our relationship and the proposal. We decided to “go public” after privately sharing our story and video with family and friends and seeing the incredible positive ripples of impact it was making. We may not personally know you, but we hope our story will shine that same life-affirming love and light we cherish so dearly into your life and your relationships.
We thank everyone who has supported our journey, and especially ALL those who helped pull off this truly unforgettable proposal. A special shout out to Small Hour Films for the unbelievable job with the video. And finally, a huge thanks to Stacy and HowTheyAsked.com for helping us share our story with you!