It's Personal

How I Planned An Epic Proposal For My Boyfriend at Walt Disney World

March 11, 2018

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I'm Helena!

A sunny gal from Cali living in the south of France. I adore slow living, magic, and celebrating the simple joys of daily life. I’m a self-proclaimed Disney nerd (as is my husband!), obsessed with cats and cocoa, and you can often find me swimming with the fishies in the salty sea. Come along and enjoy the magic, the simple joys of life with me...



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When Alex and I sat in front of his parent’s house in September and decided to get married the following summer, I told him it was important to me that I be doing the proposing. But when it came down to begin the preparations, I had no clue how I would plan it.

Planning the Proposal at Walt Disney World

I started brainstorming proposal ideas that seemed meaningful and personal to us: a camping trip, hiking a mountain, a last-minute trip to somewhere exotic – maybe a rainforest? But then it hit me: we had flights to Walt Disney World in a mere 3 months. And both of us being huge Disney nerds, I couldn’t think of anyplace more perfect than the happiest place on earth. With Disney World set at the destination, next came where in Walt Disney World.

Picking the Proposal Spot

I researched articles and watched Youtube videos on different planned Disney proposals, but none of them fit us. They were too stereotypical, obvious and all had been done a million times before. It was also imperative that it was done in private with no people surrounding us. I finally narrowed it to three choices: aboard the Mark Twain riverboat as we sailed around the Rivers of America, hiking the Swiss Family Robinson treehouse and finally – my chosen spot – a secluded, tucked away cove on Tom Sawyer’s Island, surrounded by lush Floridian trees, sparkle river water, and Cinderella’s majestic castle far in the distance. After an hour of watching Tom Sawyer Island tours on Youtube, I found it and immediately declared it as the spot I would ask the love of my life to marry me.  It was perfect. And everything about the location described us: childlike goofballs who loved to roam and explore the great outdoors, just like in the adventurous stories of Tom Sawyer. I loved how one had to trek off to the quieter Fort Wilderness off the main island and venture into a dark “No Escape” tunnel before discovering the hidden gem, and I loved how hardly any people wandered into this tucked away area.

Or so I thought.

This is the part where I give the marriage proposal advice that I wish was given to me:

Always have a Plan B.

With our 5 day itinerary mapped out, scheduled overpriced rose petals and champagne delivered to our hotel room by Disney, and a custom made compass locket in my pocket (the item I chose to propose to him with) – we flew off to Walt Disney World. I was beyond giddy and excited, despite him knowing I would propose to him at some point during the trip, and on day 2 of our 3 day of park-hopping, we made a dash to Tom Sawyers Island. With time would come more crowds, and we both can’t deal with the attention. On the raft over to the island, I sensed swirling butterflies and tangled knots in my stomach. Growing silent, I pulled out my vlogging camera and began documenting our journey while I calmly dealt with my nerves. But the crowds were large. The children were whining. And I had this feeling that what I had chosen was all wrong. By the time we had exited the dark tunnel and basked in the glowing view of the views and river surrounding us, and as I began to get down on one knee and pull out the ring box, a child bombarded past us, screaming and crying to his parents. A few families followed close behind, and I realized that maybe the Magic Kingdom wasn’t such a quiet and peaceful place to propose marriage after all.

Game over for Helena.

Alex and I left the island. And I silently mulled the whole thing over in my head, wondering why I hadn’t thought of a backup plan. Why hadn’t I thought of alternatives? Why didn’t I plan this correctly? We sat on the shaded sidewalk in my favorite hidden alley along Main Street, right across from the voice studios. Silently, I began thinking – maybe…here?

Allowing the Universe Decide

I had to propose that day. The overpriced gift basket and rose petals would be in our hotel room that evening, and it was already paid and delivered by now. But I decided at that moment to give it up to the universe, to let it decide, instead of me. The day passed. Opportunities never came. Hollywood Studios seemed more appealing as the very popular (and crowded) Magic Kingdom began rubbing me the wrong way. So, we left and we vlogged and ate way too many Mickey Mouse ice-cream bars at Hollywood Studios. Alex giddily gawked at the Star Wars characters as they passed, and I persuaded Alex to ride Tower of Terror twice in a row. As the night wore on, as we waited in line for Aerosmith’s Rock ‘n’ Rollercoaster, we began singing our favorite Aerosmith songs. Alex and I have often described our relationship as a rollercoaster: the excitement, fun and multitude of changes in the past 3 years have made us both fired up to want to keep riding it over and over again, despite the ups and downs and twists and turns of sharing a life with another human. The sharing and compromising, the arguments and resolutions…we are a rollercoaster of love and a rollercoaster in life. In that moment, I decided to ask the kind Disney cast member if we could wait and request the front car of the coaster. As the red light steadily shined, preparing to turn green, I turned to my joyful boyfriend of three wonderful years, and opened the ring box, “Alex, will you marry me?”


We instantly shot from 0 to 60mph, through pitch black tunnels and neon donuts, singing along to Aerosmith’s Sweet Emotion, holding hands and Alex holding tightly to the white ring box.

Looking Back

Walt Disney World, and our now beloved song by Aerosmith, holds special memories in our hearts as we move forward in our marriage together. I realize that life doesn’t go as planned and despite having had organized and prepared every moment of our proposal to a T, I couldn’t have expected things to go exactly the way I wanted to. Sometimes you just have to surrender. You have to throw up your hands and surrender to love and spontaneity. And it turned out to be better than my original plan. Our proposal captured our relationship far more better than the relaxed and quiet spot on the island. Screaming children were nowhere near around, rock ‘n roll music was playing in the background and a high speed rollercoaster experience was just ahead of us. Our life is not quiet, and our love isn’t either: it’s exciting, electric, untraditional, uncomplicated-ly simple (yes, I know that’s not a word) and intuitive. But most of all, it’s fun. We embrace fun, and my proposal to him couldn’t have been more fun than a rollercoaster ride. With Aerosmith blasting in our ears.

To read more about why I decided to propose to him and why he’s taking my name, check out this post!

Helena Woods I Proposed to my boyfriend and he took my last name! Robyn Middleton Photography

Engagement Video


Let’s Encourage More Women to Propose – Pin This!

i proposed to my boyfriend...and he took my last name

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  1. Alex says:

    This blog post is so amazing! It’s so true that life can throw you curveballs, and all you can do is adapt with what life gives you. Love this 🙂


I'm Helena, your new kindred spirit.

Sunny free-spirit, writer and creator in love with documenting the simple joys of life. I am passionate about noticing light and truth around me and reflecting it back to others.

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