Haley and Caleb

Proposal Ideas Haleakala National Park

How We Met

I saw Haley for the first time when we had both arrived for a year-long internship on the island of Maui. I’m from Georgia and she is from Colorado, so we had never crossed paths before. We had both been selected to work in different departments at a church called Hope Chapel. The first week was full of surfing, warm welcomes, and getting to know the 10 other people that we were about to spend the next year with. Haley and I never actually formally introduced ourselves to one another, but I started noticing her early on. I would hang out near her office and throw paper airplanes or shoot rubber bands at her to get her attention. Sometimes I would draw pictures or write notes and leave them on her desk. Over the next few weeks we developed a close friendship and shortly after we knew that we liked one another. We didn’t start dating for another six months though, since we lived in close quarters and worked with one another.

In January, about halfway through the internship, a group of us went to Nepal for a humanitarian aid trip. We saw Mt. Everest together and although that was great, my favorite part was when I asked Haley if we could go on our first date when we got back to Maui and she said yes! We dated for the rest of our internship, and even though it held many ups and downs, we always came back together as a team, realizing that we were better with the other by our side. As our internship came to a close we decided to stay on Maui, we had made many friends and built a community here. It wasn’t easy to figure out how to live in Hawaii as a young adult, and sometimes it seemed crazy to think that we could make it here, but the way that we loved one another made it all worth it.

Engagement Proposal Ideas in Haleakala National Park

How He Asked

Caleb had told me that we were going up to Haleakala to watch the sunrise with his brother who was visiting us. It’s a popular thing to do on Maui, and something that we love to do together, so I suspected absolutely nothing. We woke up at 2:30 AM, made coffee, grabbed blankets (because it’s cold on top of a 10,000 ft mountain even in Hawaii), and headed up to the top. It was still dark out as we hiked to the top of a hill that we usually sit on. We found a nice spot and settled in. About 15 minutes before sunrise his brother told us that he had to go to the bathroom and left. What I didn’t know was that he had gone back down to the bottom of the hill to get two of Caleb and I’s best friends (who had also gotten up at 2:30 to take photos and video of the proposal). I mentioned that he had been gone for a while, so Caleb went to go look for him. Caleb came back a little distressed about 5 minutes later (apparently because his brother couldn’t find our friends).

Haley's Proposal in Haleakala National Park

I didn’t think much of it though, we talked nonchalantly for a bit and then right before sunrise he changed the subject of the conversation. He started talking about communion and the covenant that God makes to us to never leave us or forsake us. Then he said, “I want to make that same covenant with you.” I said back, “Thank you!”, because I still had no idea what was going on, thinking that he was just saying something nice. Right after that he stood up and immediately I knew what he was doing. He pulled out the ring, told me that this might be the closest we would ever be to heaven on earth and that he wanted to spend the rest of his life with me. Caleb asked if I would marry him and I nodded my head yes, not realizing I hadn’t actually said yes out loud until he asked me again to make sure. As I went to hug him I noticed people moving behind us. I turned around and saw our friends who had come up to document everything. Loudly I said, “Have you guys been here the whole time?!”. Of course they had. We rejoiced, took more pictures, and then Caleb told me he had a surprise brunch planned with some of our friends.

On our way down the mountain, I tried calling my mom and dad, but they didn’t answer. I know I couldn’t really tell anyone else without telling them first so I just kept calling and calling. Eventually, we got to brunch at one of our favorite spots on Maui, Sarento’s. We walked in and as we rounded the corner I saw my dad in one of his unmistakable Hawaiian shirts. Quickly after, I realized my mom was sitting right next to him. My hands flew up to my face, I couldn’t believe he had brought them out for our proposal! But it got even better, at the same table with their backs to me were three girls. One of my best friends has easily recognizable red hair, so I immediately knew that it had to be three of my best friends from back home in Colorado. They all turned around and I was beside myself. All of these people had flown out for this day and to spend a week on Maui with us. It was the greatest day ever! We rejoiced some more, ate some really awesome food and spent the whole day celebrating and relaxing by the pool. They promised no more surprises too.

That night we were heading to what I thought was a dinner with my family and friends. We pulled up to the restaurant at the hotel and walked inside. They led us to a private dining room and when we walked inside we saw so many of our Maui friends who had come to celebrate our engagement. My parents and new fiancé had an amazing dinner planned and we celebrated again that night. Three huge surprises in one day and it was the best day ever. Caleb and I felt so loved and encouraged in our new adventure. We can’t wait to see what the rest of it holds!

Special Thanks

Anna Winegarner | 
Photographer
Isaac Haaland | 
Photographer