Blog Post,  Disney Resorts

A Disney Proposal – A Most Magical Christmas

By the time this post goes live, Ben and I will be enjoying part 2 of our honeymoon, down in Walt Disney World, so it seemed as good a time as any to share the story of our Disney proposal.

On December 26, 2017, Ben kicked off our Disney vacation by proposing to me. Hopefully by now this isn’t a spoiler — I said yes! For months, and I mean months, before the trip, I knew it was coming, so here’s a little peek into the most impatient 8 months of my life. Seriously. I knew for 8 months.

Before the Trip

I feel like I know Ben really, really well (good thing, since I’m, you know, married him, right?). That said, he’s still a very subtle, tricky man when he wants to be. For who knows how long, he was slowly collecting information on what would be the perfect proposal for me. Where would I want it? How would I want it? When would I want it? What kind of ring would be best? Ben would carefully curate conversations to be able to sneak in little one-off comments on which he could gauge my reaction to plan this momentous event.

@castleboundkim

In May of 2016, pretty early in our relationship, actually, Ben and I were in Disney and passed a couple wearing those “Happily Ever After” buttons. Ben asked “Would you want one of those someday? Get engaged here, get married here, honeymoon here, spend an anniversary here…wear the button?” I played right into his hands. “Of COURSE I would! Anything that’s special somewhere else could be more special in Disney.” I should have heard the scratch of the pencil as he made that mental note.



On other occasions, I was extraordinarily NOT subtle about my preferences. I made it clear that I wanted our “couple events” (engagement, wedding, etc.) to be special in their own right. I, personally, didn’t want to get engaged on, say, Valentine’s Day, because I wanted our engagement day to be special simply because we got engaged, even though Valentine’s Day engagements can be incredibly romantic. Somehow, Ben got me to admit that “near” a holiday is completely fine, without me noticing what was happening, even as we planned a Christmas trip back to Disney World. How does that not scream “Disney proposal!”?

Disney Proposal - Button
Kate Michaud Photography

My conscious mind was completely bamboozled as he slowly picked out each detail of our Disney proposal, until one night in April I woke up at 3am — cheesy cinema style — sitting bolt upright and knew, suddenly, without a doubt “Ben is going to propose to me in Disney on the day after Christmas.” The waiting game had begun. I immediately texted my best friend, KJ, because I didn’t know what else to do. I didn’t want to ruin the surprise! If there was one person who couldn’t know I knew, it was Ben.

Obviously, like any sane person would, I began to think of nothing else. Where exactly would he do it? How was he going to ask my parents? How would he know what ring to pick out?! WHAT WOULD I WEAR?!?! I love Disneybounding, but did I really want to be dressed like one of the 101 Dalmatians when Ben got down on one knee?



I started obsessively planning. Suddenly, the only pictures being pinned to my Pinterest board were rings I liked. I’d definitely need to get my nails done before we went to Disney — hand pictures were coming! I was going to get a Disney proposal!! I couldn’t stop playing out scenarios in my head and even came up with a top four list (I know, five would be much cleaner, but I couldn’t think of another possibility) of where he might pop the question in ascending order of likelihood.

4. On a ride. Ben knows Disney rides like the back of his hand. He’d know exactly where the pictures were and would know exactly when to take out the ring. This option was least likely because risk of losing the ring is uncomfortably high.

Seven Dwarfs Mine Train
@castleboundkim

3. PhotoPass photographer in front of the castle. I mean, come on. It’s the CASTLE! No doubt it’d be magical. Not so likely because crowds would be unbelievable around that time of year, and something so public didn’t really feel like “us.”

2. At California Grill. We had a reservation for California Grill on the fourth day of our vacation and I know it’s Ben’s favorite restaurant on property (and really high up on my list, too). Could you see it? Standing outside, watching the fireworks, and listening to Happily Ever After, and then down on one knee he goes. This one felt like a likely choice, but I was personally hoping it wasn’t a winner, because then I’d have FOUR WHOLE DAYS down in Disney for me to lose my mind waiting for dinner. (I joke now that if he hadn’t proposed right away once we got to Florida, I’d be shouting “YES” every time he bent down to pick up a found penny. I was a hot mess.)

Disney Proposal - California Grill
@castleboundkim

1. At the Wilderness Lodge. Ben and I both adore the Wilderness Lodge, it’s our home resort for DVC, and we would be staying there on our first DVC trip for Christmas. Often, after the parks are closed and we drag our feet back to our hotel, we love to walk around those beautiful grounds and just enjoy the quiet. I could see some secluded place on that piece of property, on one of those late-night walks being the perfect place to agree to spend the rest of my life with Ben.

Wilderness Lodge - Christmas Lobby Disney Proposal
@castleboundkim

I could go on and on about the lead-up — I do have 8 months of crazy-brain thoughts after all — but I think it’s time to get to the main event.

Down in Walt Disney World

Ben and I took the first flight out of Providence, Rhode Island the day after Christmas. We woke up at some ungodly hour and headed off through the snow (wearing flip-flops like crazy people because we knew Florida would be warm) to the most magical place on earth. Our flight, mercifully, went smoothly and everything was on time.

Ben seemed unusually anxious, but I guessed I knew why and pretended not to notice. (Little did I know, he had a plan for everything. For example, if they asked to search his suitcase, he was going to tell me he got a notification on his phone that our gate changed and send me over to the board of departures to double check.)



We hopped on the Magical Express and we were off! We got to the hotel between 10 and 10:30 in the morning. With check-in not until much later in the day, it was not at all surprising that our room wasn’t ready. We were going to have a 6th floor room with a view over Bay Lake.

Alternatively, they had a first-floor room looking out on a quiet walkway available immediately. In a very un-Ben-like fashion, he seemed to want to take the move-in-ready room. I did not protest at all. Man had a plan and I wasn’t going to mess it up.

Wilderness Lodge Pool
@castleboundkim

Since we had flown in from a sub-zero, snow-laden winter wonderland, we both quickly changed into Florida-appropriate attire and took off. Ben suggested we walk around the hotel because it was my first time at the Lodge without it being under construction for Copper Creek. I really did want to see all the new stuff without tarps and scaffolding all over the place. We walked outside first before getting back to the lobby.



If you haven’t seen the Wilderness Lodge lobby during Christmas, make it a to-do. This massive, seven-story lobby was made for Christmas. The log-cabin feel and smell are perfect for the enormous, glittering Christmas tree looming over twinkling lights, wreaths, and the coziest fireplace ever. It’s breathtaking.

Ben made a beeline for the stairs and began the climb to the top balcony overlooking the lobby. The view would be best from above, he assured me. His adrenaline-fueled muscles seemed to teleport him up those stairs, while I huffed and puffed my way up like somebody on the last leg of an uphill hike. Man, I needed to work out more. At each landing, he glanced around, and moved on. No comments, no savoring the moment. Ben was booking it. Eventually, we made it to the tippy top and the space was deserted.

A Disney Proposal

Wilderness Lodge - Disney Proposal Location
@castleboundkim

He waved me over to the balcony railing, centered with the Christmas tree and I had no words. He asked me where we were. I said, “We’re home.” (Insert private, sentimental sweet nothings.) Then, Ben put his hand in his pocket, and I realized, “OH CRAP! THIS IS HAPPENING NOW!!! My Disney proposal!!!” With classic traditionalism, he got down on one knee, popped open a little brown box, and asked me if I would marry him.

Thankfully, I was able to remind my brain to make words to actually say, “Of course I will!”

We each called our Moms (his started immediately screaming and mine burst into tears). Then, we moved on to calling our Dads, at which point we began walking toward the busses. We had a FastPass for Test Track to catch, after all. Completely in a daze, this was when I walked right off the ground at the top of a flight of stairs and nearly threw myself through glass doors at the bottom. It was all in all the best day ever.

Hi everyone; I'm Kim. It'll come as no surprise that I'm a huge fan of all things Disney. I'm also a crazy cat lady (currently without cats), spastic crafter, and amateur Disneybounder. Living up in New England, I don't get to the parks as often as I'd like, so I try to bring Disney into my life at home, and hope to show you how to do the same!

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