A Fairy Tale Proposal at Walt Disney World

Did I say “Fairy Tale”? Because what I meant was… This is our “I completely ignored all the obvious signs that Roo was going to propose and somehow still managed to ruin his plan” story.

I grew up in Florida and have always been completely wrapped up in the magic of Disney. I have so many great memories of traveling to Walt Disney World for birthdays and family vacations, and during my university years my friends and I were all so close to WDW that we may have made a few day trips to Epcot.


That’s little me in the Mickey ears with my cousin. Gotta love 80’s hair.

But once I moved to Atlanta, I had a 4-year dry spell in the magic department and never made another trip back to the kingdom (or anywhere else inside those walls). Mr. Rooster knew this, of course, because of my incessant rambling about how much I wanted us to take a trip to Disney together. Every time there was a commercial, or a new Pixar movie, or even when somebody said “mouse,” I always mentioned how badly I was dying to take a trip there with him. You see, Roo has always thought Disney was “a kids thing,” and as a native Floridian and unofficial ambassador to Disney World, I had to prove him wrong.

WDWgateWDW Hints

Eventually he realized I wasn’t going to stop nagging him felt really strongly about it, and for Christmas in 2012, Roo got me a 3-day ticket to the parks. We planned the trip for May 2013, and it just so happened to coincide with our 4-year dating anniversary. How perfect! I even was lucky enough to score some bonus park tickets through work. Enough, in fact, to invite my best friend (and future MOH) and her boyfriend to come along on our little vacation.

Did I mention how oblivious I was to this whole plan? Yes? OK. Let’s move on.

So May 15th rolls around, and Roo and I get up early in Atlanta on the morning of our 4th anniversary to start on the 6-hour drive to Walt Disney World.


We’ve done early morning road trips before, so I know the drill. We both convince ourselves we’re going to pack the night before, but then we just end up just watching TV and deciding we’ll get up early to finish packing before we head out on the road. Oh, and Rooster always wears sweatpants. Always. But on this, the morning of our 4th anniversary and the day we leave go to my favorite place in the world, he put on jeans. His good jeans, y’all.

I even noticed he had nice jeans on. I commented on it. And we both laughed. He said it was because we were stopping for lunch in Gainesville (my college town) on the way there. And I just shrugged and believed him. I decided I should put on real pants too.

…But the thing is we always stop in Gainesville for lunch when we drive to Florida. And he always wears sweatpants. See? Me = Oblivious.

Glee Wiki

So, fast forward: We get to Gainesville and pick a quick spot to order lunch from a counter so we can get back on the road to the happiest place on earth. As we’re eating, Roo casually mentions that we should go walk around the football stadium. “Ummmm…. why?” He says that maybe I could walk around and take some pictures. “Um…. I have lots of pictures of the stadium. And I really want to get to Disney World. So let’s just get on the road.”

Roo would later tell me that he planned to propose right there in that there stadium. Oops. We could have added, like, three glorious hours to our total engagement, but dumb old me had to go and squash his plan. Bummer.

Luna Bella Photography via Festive Finds

This could have been us!

Eventually we get to Orlando, and since I am an experienced Disney veteran, I have planned every single detail of our trip itinerary to maximize time in the parks (Extra Magic Hours, y’all) and to coordinate with our friends who are arriving in a couple days. The scheduled entertainment for the night of our arrival was to check in to the hotel, then immediately head out for dinner and drinks at Downtown Disney, since he’d never been there before.


Head out after we take a picture of our Towel Mickey on the hotel bed, of course.

At this point I want to mention that I noticed Mr. Rooster acting super weird the whole night on the way Downtown and as we’re there hanging out. First, he insisted on being on my right all night. He made me switch seats on the bus, and was super clumsy trying to always switch sides as we held hands walking around. Second, Roo was uncharacteristically curious about the whole place. He kept asking me what was down this way and that way, and insisted that we stroll along the quiet little lakefront instead of heading in for a pint and some nosh like I thought we would do.

He persisted in his efforts, despite me being completely obtuse, and spent a while checking out all the spots around Downtown Disney that he might decide to pop the question. There was even a hot air balloon set up when we went, which turned out to be another big clue that I completely ignored. Roo was all gung-ho about paying $20 apiece for 10 minutes in a balloon, and was seriously and genuinely disappointed when they told us it was grounded for the night due to high winds.


The balloon at Downtown Disney. How cool would that have been, right?

Eventually, he found a quiet gazebo off the main path lit up with string lights and got down on one knee. SPOILER ALERT: I said yes and we immediately celebrated with a pint at an Irish pub, toasting to our first vacation together as nearly-weds.


The spot.


The ring. More on that here.


Us celebrating a few days later with our friends and a glass of champagne from France in Epcot.

We also got some sweet swag for celebrating our big moment with Disney. If you’re celebrating anything like a birthday, family reunion or graduation at the Disney Parks, let somebody inside Guest Relations know and they’ll hook you up with a free Celebration Recognition button.


::TV COMMERCIAL FINE PRINT:: Possible side effects include getting your shirt caught in a roller coaster harness, and making every person around you compelled to say “congratulations.”


It was all so wonderful, and so so strange. Did I make note of the fact that my boyfriend of four years—that day—had planned a trip to my favorite place, dressed up from his usual garb and spent the whole night acting so weird? Yep. Did it ever even once pop into my head that me might be proposing, even after we’d been ring shopping together? Nope! But you know what? I’m so glad that I never caught on. Even though everything was stacked against it, the proposal still managed to remain a total surprise, just like we’d both wanted.

I’m telling you. It’s that Disney magic, y’all.

07. February 2014 by Taryn
Categories: Life | Tags: , | Leave a comment

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