Shelby’s Version 

Let me preface by saying it has always been my dream to be proposed to in front of the castle at Disney World. ALWAYS. I used to joke with my sister that if that’s not how it happened, I would say “no, try again please.” Now that being said, Alex did not know this information. As I grew older and reality set in, I sort of threw that dream out the window because I was going to be happy no matter where it happened. It would just be a major bonus if it was a Disney proposal. So, I never mentioned it to him.

Now, onto the story. For me, I didn’t see it coming. There was a part of me that hoped it might happen because hello…it’s Disney and what I’ve always wanted. But, I wasn’t going into the trip expecting it. The trip was planned spur of the moment in November 2020 for us to go two months later at the end of January 2021. Alex randomly texted me over Thanksgiving break and said “Let’s go to Disney World” and I blew it off for a bit because I didn’t think he was actually serious about going. Then the next day we had the trip booked! 

Next up was making shirts and planning outfits. You know, gotta figure out which ears I’m wearing with each outfit because…Disney. Alex didn’t care about the shirts, so I made him some anyway. Fast forward to the night we were packing. Alex started asking about my shirts and which ones I was wearing on what days. So in my head, I’m like…when has he EVER cared about what I’m wearing?? That was weird to me. But, whatever, I told him which shirts and I had set to wear my “Best Day Ever” shirt on the last day. Not because that was going to be the best day ever, but because I had specific shirts I wanted to wear to specific parks and that was just the shirt leftover for the end of the trip that I didn’t have a specific park for. When I told him I had it for the last day, he started questioning it and convinced me to wear it the first day since that would technically be the best day ever, since it’s the day we got there. So, I changed my shirt plans, again. The day we left I wore my “Disney Bound” shirt. As soon as we got to the resort I went to the lobby bathroom to change into the “Best Day Ever” shirt. We dropped our bags at bell services and went straight to Magic Kingdom!

We walked down Main Street to see the Castle in all its glory. We found a PhotoPass Photographer and had our picture taken right there in the front. It was so bright I could barely hold my eyes open for the picture! So, I wanted a different picture that our faces would look okay. I asked Alex if we could go around to the left side of the Castle and try over there. There just so happened to be another photographer on that side, so we went to have our picture taken with her. Alex started asking the lady if we could move around towards the bridge…I was super embarrassed and told him the lady knows what she’s doing, just take the picture here where she normally does it! I was a little curious about the spot he was trying to go to, so I was turned to look at it and when I turned back to face the camera he was on one knee with the most beautiful ring in his hand! I started crying immediately and he said: “Will you spend happily ever after with me?” And I think you know what my answer was 🙂

Alex’s Version

I first went to Disney World when I was 7 years old. It was a big family trip for Spring Break, 1999. What was my favorite ride? Nothing. I was scared of everything. So, what does a 7-year-old do at Disney World when he is scared to ride anything? You feed that kid and let him meet every character in the parks.

Shelby and I had talked about how fun it would be to go to Disney World at some point in our relationship, but it was never a big, serious conversation. We spent Thanksgiving 2020 with our own families, and to say I missed her would be an understatement. Now, I already knew I wanted to marry this girl. I had known for a while. I was laying in bed Thanksgiving night and decided right then that I wanted to take her to Disney World and propose to her. So, I texted her and asked if she would want to go after Christmas. Well, that was a bit too ambitious, so we decided on the last week of January 2021 and quickly booked our trip.

I was a little nervous that she may suspect something, but my birthday would be that week, so it seemed like the perfect cover story. Once things were booked I called our travel agent, Whitney, to talk about the REAL reason for the trip. She freaked. Well, for more reasons than one. She told me she had actually asked Shelby if she thought I was going to propose. She said Shelby shook it off and mentioned my birthday was that week, so that wasn’t really plausible. Already, this little plan was working.

So, December and January were spent planning every detail to make this proposal happen. How do I get the ring there? Where am I going to pop the question? Will it be photographed? This was stressful stuff. My greatest concern was that I wanted her to suspect nothing because if we were able to pull it off, it would be one of the greatest moments for Shelby.

Sunday, January 24, 2021, we land in Orlando around 11:30 am. The ring successfully made it through security tucked away in my backpack and I was feeling good. We got to the resort to check-in and drop our bags, and Shelby really wanted to change her “plane ride Disney shirt” to her “Best Day Ever” shirt. Of course, you’ve already read how I influenced that decision. While she was making her wardrobe change, I quickly took the ring out of my backpack and tucked it into my pocket. There was no turning back.

We quickly got onto the shuttle to head to Magic Kingdom. She was sitting on my left. Why am I pointing this out? Oh, because the ring was in my left pocket and she set her hand on my leg during the ride and was LITERALLY TOUCHING THE RING! Pretty sure I almost had a heart attack, but we continue on. Yes, my version is WAY longer than Shelby’s because more was obviously going on.

Finally, we made it to Magic Kingdom. Music was in the air. It was the perfect day, about to be made more perfect. We took some pictures in front of the Walt & Mickey Partners statue and were completely blinded by the sun. Yikes. Then we equally wanted to go around to the left side of the castle where there is a bridge. I was trying to be non-chalant about it, but just knew I was blowing it. But, there we were. At THE SPOT. Our travel agent Whitney had been there the week before on a work trip and was scouting locations, and this was THE ONE.

The moment was finally here. After months of preparation, the flight to Orlando, and the ring securely in my pocket, it was time to ask the girl of my dreams to live “happily ever after” with me. Best. Day. Ever.