Disney World Proposal & Engagement!

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This is our Walt Disney World engagement story from November 2007. We got engaged on the beach of the Polynesian Resort during the Holiday Wishes! fireworks. If you’re planning a surprise proposal at Walt Disney World, hopefully this story can serve as some inspiration for you!

I began planning how I would propose to Sarah prior to our August 2007 trip. I knew I wanted to do it at Walt Disney World, and I knew around Christmas-time would be perfect (as that would mark being together for two years). Not wanting her to suspect anything, I suggested a Christmas Walt Disney World trip on our return from Walt Disney World in August to see whether she’d be receptive to the idea (of course, she was). While such a return visit would stretch our budget as students, I wanted to propose the right way, and I knew that would be it.

After the trip was set, I wrestled with some ideas in my head, but had nothing fully solidified. I decided to post in the WDWMagic forums. Since Sarah commonly lurked the forums, I went all out, creating an alias and soliciting feedback on some of my ideas. Based upon that feedback, I devised a plan, and set it into motion.

The process started the night before we left for Walt Disney World, when I voyaged into the one place no man should ever go: a woman’s closet. There, I sought to find a dress for Sarah to wear to dinner the following evening. I located what I needed, but left it there, knowing she would head into the closet again before we left and would suspect foul play if any of her clothing was misplaced.

The following morning right before we left, I went back upstairs to grab my backpack which I had “accidentally” left behind. While grabbing my bag, I slipped into her bedroom and quickly grabbed the dress and threw it in my bag. We were living in Valparaiso, Indiana at the time, so we had to take a series of our car, and trains and buses to get from Valparaiso to Chicago’s Midway airport. From there, we were off to Walt Disney World!

After arriving at Port Orleans Riverside resort (my first time staying there since it changed from Dixie Landings), meeting our friend, and checking in, we went to Dowtown Disney. During our trip planning, I had told Sarah we would mini golf that night. I could tell she wasn’t thrilled by the prospect (which was good, since I didn’t want to plan something too fun so she would be disappointed by the eventual change in plans) but she agreed to go anyway. The boats on the Sassagoula River should be one of the most relaxing experiences at Walt Disney World. Not for me. My nerves were boiling. When we arrived at Downtown Disney, we grabbed some sandwiches at Earl of Sandwich, then wandered around for a bit before taking the boat back.



After we returned to the resort, we wandered around some more, before leaving to go mini golfing. Our friend, Nick, who was doing the Disney College Program left for “work” after having secretly given me a couple bottles of champagne and wine, and we returned to our room. Not wanting Sarah to see the bottles and get suspicious, I hid them at the edge of the bed.

Then I informed Sarah of the ‘bad news.’  I unfortunately had to change the plans. At first she was taken aback, but I informed her that we were going to dinner instead of mini golfing. When, after asking what I was wearing, I responded “suit”, she was taken aback yet again. She had not packed any ‘dressy’ clothes. I pulled out a black dress, and asked if that would work for her. Surprised and elated, she responded affirmatively.

We got dressed and prepared to leave. I told Sarah I was going to take the tripod so that we could take pictures after dinner. So I put in my backpack, along with the ring (which was the true motivation for taking the bag, since the ring stuck out like a sore thumb in my pocket), however, I intentionally left the bag in the room when we left the room.

About halfway down the stairs, Sarah noticed that I “forgot” the bag. I told her I would run upstairs and get it, and that she should just wait. I rushed back to the room, threw the champagne and wine in the fridge, and grabbed the bag. Off to dinner we went, with about half the plan going perfectly.

Having had no failures thus far, I knew something in my extremely precise plan was about to fail…I just wondered what. After a bus ride from Port Orleans Riverside to Magic Kingdom of Sarah trying to guess where dinner would be, we headed for the monorail. Sarah kept guessing, and I got up from our seat at every monorail stop, only to sit right back down. I’m not sure how amused she was by this, but she laughed throughout the journey. After heavy delays, we finally arrived at the Grand Floridian 1 minute after our reservation time. We quickly made our way to Narcoossee’s.

The hostess informed us our table would be ready shortly. This precise plan relied heavily on us seeing the fireworks, and I hadn’t thought of any contingency plans, so this had my worried. My brain started to scramble as I quickly thought up a backup plan in case dinner took too long.

About five minutes later, my buzzer went off. Phew. We enjoyed dinner (at least I think we did–I was so nervous that I don’t think I tasted any of my food!), although towards dessert, I informed the waitress we would like the bill with dessert, as we were in a hurry. She kindly obliged, and I thanked her.

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After dinner, we headed out to the dock to take the ferry over the Polynesian. We got there 10 minutes before the fireworks started. The night was chilly by Florida standards, so I gave Sarah my coat to wear.

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I set up the tripod, as I thought it would be nice to get some pictures of us with Christmas Wishes in the background–at least this was how I explained it to Sarah. I had watched a video of Christmas Wishes several times on YouTube, so I knew exactly how the dialog corresponded with the grand finale, which was when I planned on concluding my proposal.

Right before the grand finale was going to start, I told Sarah that then would be a good time to get a picture of us with fireworks in the background. So I set the timer up, and went by her side (she didn’t know I set the camera to take 10 pictures with a 2 second lapse between). This is when I planned on proposing.

Unfortunately, I forgot to press the shutter. I ran back over to the camera pressed the shutter, and hoped things would still time perfectly. The first shot fired, so I knew it would work this time. I ran back to Sarah.

I stood next to Sarah for what felt like an eternity but was probably only a second or two, planning our “pose”. Then I dropped to a knee, and began. I planned on delivering a long and meaningful proposal, explaining how important she was to me, but I was incredibly nervous, and I have no idea what I even said now. I am pretty certain that it was anything but well-spoken. I don’t think she really heard or remembered anything I said anyway, and after getting over the initial shock, she said yes.

The pictures lined up perfectly, for the most part. I took these well before I knew anything about photography (they were all taken with a cheap point and shoot camera), but to date they are my favorite pictures that I’ve ever taken, and probably will be until we have kids. I think they speak for themselves:

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And that’s the story of our Walt Disney World proposal! Afterwards, we went to the lobby, called our families, etc. We then returned to the resort, where we enjoyed chilled champagne while I spilled the details I had so difficulty kept from her for the past months.

The rest of the trip was an amazing time as we basked in the after-glow of the engagement. Since I originally wrote this post (shortly after returning) and shared it, we’ve since gotten married, taken our Walt Disney World honeymoon (click here for the trip report), taken our first trip to Disneyland together (click here for the trip report), and shared multiple other Disney trip experiences.

Did you enjoy this Walt Disney World engagement report? If so, please share the post on Facebook with a “Like” or “Share” through the buttons at the top of the post, on Twitter by clicking the “Tweet” button, or by sharing it through the random assortment of buttons below! As always, please leave your thoughts about this post in the comments!

45 Responses to “Disney World Proposal & Engagement!”
  1. Dean Lewin January 8, 2017
  2. Sara Hendrickson September 16, 2016
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