Kaylyn and Matthew

Kaylyn's Proposal in Maui, Hawaii

How We Met

It all started on my first day at a new job with a local start-up company. It was my first day of work and I accidentally sat in someone else’s seat for the team meeting – and that someone was Matthew. I was shy and embarrassed, but that quickly turned into becoming close friends with everyone at work. Soon after, we were best friends for the next 3.5 years. He was the person I turned to when the best and worst things happened to me in life and the person who I wanted to talk to every single day. Eventually, my best friend turned into my boyfriend, and I quickly knew he was the person I wanted to spend the rest of my life with!

We went on a trip last year at this time to Maui with my family and witnessed them renew their 30-year wedding vows – celebrating at a restaurant called Merriman’s afterwards. One year later, he got down on one knee in that exact spot and became my fiance!

Marriage Proposal Ideas in Maui, Hawaii

How They Asked

It was a rainy morning and my family talked about dressing up and getting family photos – including the annual Christmas card photo! We ended up all getting ready, then we were on our way to our favorite place – Merriman’s! Since it was closed due to Covid-19, we still wanted to get photos there with the pretty views and figured it would be great since it would be empty. When we got there, I saw a man setting up a drone where I immediately gave him a little wave – I was so jealous he was getting such amazing drone footage since all the beaches were empty and hoped my family wouldn’t ruin his shots! Matthew insisted we had to walk out on the rocks and take a selfie, which he made us do in the same spot a couple days before, but now I know he was just scoping the place out! I got a big splinter in my foot as we were walking to the rocks (just my luck), and proceeded to give him a hard time because it was hard to walk on my foot and walk on the rocks in sandals… little did I know once we got out to the beautiful view, he’d ask me to marry him – in my favorite place with my family all watching from the hill above! I said yes!!! :)

After the engagement took place, Matthew and my whole family started telling me about all of the planning that went into the proposal. I had no idea that Matthew made reservations at Merriman’s 3 months prior, received permission from the General Manager for a large dinner party (their max reservation was for 8 people), had a ring box custom made from Australia, booked a videographer, and planned all other logistics with my mom and dad. Everyone had to heavily improvise when Maui announced that they were shutting everything down on the island due to Covid-19. However, my fiance didn’t give up and made this more than perfect. Looking at the additional silver lining, we got the most beautiful drone shots I’ve ever seen – our special moment on an empty beach!

Engagement Proposal Ideas in Maui, Hawaii

Wedding Proposal Ideas in Maui, Hawaii

Our Video

Special Thanks

Jordan Nagasako
 | Videographer
Jordan Nagasako
 | Photographer