Four Seasons Maui Candlelit Proposal

This proposal was months in the making and included so much amazing talent here on Maui that I feel nothing but blessed to have been a part of it. Back when I launched Engaged on Maui, I tried to imagine what the most romantic proposal I could think of would be – I mean, sky’s the limit right? Maui is one of the most beautiful places in the world and there are so many amazing places here, it was tough to pick a spot.

Often I have guys ask me “If you were to be proposed to again, what would it look like? Where would it be?” And I always struggle with this. A proposal at sunrise would be beautiful. But I also like cliffs. Oh – and the ocean. The ocean is amazing, of course. But there was this one idea buzzing around in the back of my head that wouldn’t go away.

Maui is amazing, indeed, but there is something about the calmness of post-sunset, the breeze whispering through the palm fronds, and the ambient glow of candles that sets my heart on fire. That one scene from Friends always sticks out in my mind – the one where Monica proposes to Chandler – where they fill their living space with candles and proclaim their love for one another. That is what I wanted to create: something romantic, intimate, personal, and over the top. And I knew that the Four Seasons Maui was just the place to partner with.

Kayla and Laura really are the best of the best. Kayla and Laura plan events and weddings at the Four Seasons and truly exemplify the fine line between creative genius and planner extraordinaire. They coordinated flowers, the amazing tree swing, hair and makeup, and the breath-taking candlelit walkway where the proposal took place. They dotted all the i’s and crossed all the t’s – I couldn’t have done it without them. Follow Four Seasons Maui Events here and the Four Seasons Maui here to see what they’re up to!

So I had Kayla, Laura, and the Four Seasons on my team, I just needed to find the right couple. And then I thought of Josh and Heather. They are two of my dear friends that I have watched fall in love over the last two years. We met at a local coffee shop and together we hatched a plan.

A week before the proposal, I called Heather with an “emergency”. I told her that my model for this shoot with the Four Seasons had canceled last minute so I needed someone gorgeous to fill in. I have photographed Heather multiple times so she knew how to pose for me and I felt comfortable shooting her – she was in (thank GOODNESS!).

The amazing gowns she was wearing were from Rent the Runway – one for the “bridal” portion of our shoot and one for the proposal itself. There was a trunk show that week for Kimberly McDonald Jewelry, so Heather got to wear some incredibly gorgeous jewelry from her collection.

We began our shoot up at Plumeria Point with a swing adorned in flowers and lilikoi vine. As we did our bridal shoot up there, Josh, Kayla, Laura, and a small group of our friends assembled at the Serenity Pool to help set up. Because after the proposal, our friends had another surprise in store for Heather!

We finished our shoot on Plumeria Point with Heather, my assistant Amber, and Caleb from Areca Film Company (make sure you watch the video on the bottom of the post) – and headed down to our room to change for the grand finale. I told Heather that we wanted to show the ambient light of the after-dark scene at the Serenity Pool and I just needed to check in with Laura and Kayla before we moved forward. I ran upstairs, made sure everything was good to go, and then called for Amber to bring Heather up to the pool area.

I’m pretty sure I was the most nervous person there. Truly. Heather was completely in the dark, Josh stood confidently at the end of the pathway, and everyone else was cool as a cucumber. We turned the corner and Heather peered down the lit walk way. She stared for a moment, looked back at me with a confused look and I responded “You should probably go.” With that, she began to walk toward Josh.

When she reached the end of the candlelit path, he said some words to her, none of which I could hear myself, but she that smile on her face was so big it could have lit the room. Together they chatted for a moment and laughed together before Josh got down on one knee. I’m pretty sure everyone watching held their breath – it was like something from a dream. She said yes even before he asked!

Post-proposal we stayed at the Serenity pool and got some shots before heading down to our lower lawn for “more photos” – really, our friends were waiting at a beautifully styled dinner at Ferraros. We rounded the corner, and once again, she was totally caught off guard. Their son and six of their closest friends were waiting to celebrate and toast to the new chapter in their lives.

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Josh and Heather: thank you for allowing us to be a part of this monumental moment in your lives. It will be a night I’ll never forget.


A huge thank you to our amazing vendors for making this day possible:

Photography: Engaged on Maui Photographer Angie | Storyteller Package

Venue: Four Seasons Maui

On Site Coordination: Kayla McCracken and Laura Creider

Lighting and Flower Swing: Rio Event Design

Dresses: Rent the Runway

Videography: Areca Film Company

Jewelry: Kimberly McDonald Jewelry

Dinner: Ferraro’s

Flower Headpiece: Manutea nui e

Calligraphy: Ocean Ink Calligraphy

Flowers: Country Bouquets Maui


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