• Caitlin McAninch

The McAninch Proposal

Updated: Feb 16, 2019



Because it’s Valentine’s Day week, I thought it would be fun to tell the story of Dylan proposing. I wanted to tell the story mainly because it’s not really told anywhere, but also because I love looking back at this day. I’ll never forget how badly my cheeks hurt when I went to bed on this night from all the smiling I did.

Let’s start way back though. Like way back.

Dylan and I started dating summer of 2011. It was very unexpected because I wasn’t really looking for anything at the time, and Dylan was about to move to Arizona! But we met, we clicked, and it just worked.

Fast forward a few years later, after a few rounds of long distance (him in Arizona, me in D.C.), and a year of living together… it was almost Christmas, December 2015. And Dylan casually asked what kind of ring I would want. So, I went to the jewelry store and I designed the ring of my dreams.

But, no lie, that’s when I sort of started expecting it! We went to Disneyland in January; I thought Dylan was going to propose. Then we went on a few other trips, went to family gatherings, all different events. Yet, it never happened. But then! We planned a trip to Disney World, so I definitely thought it was going to happen at Disney World.

During the summer of 2016 Dylan decided we needed to go on a cruise. He wanted to go on vacation and he liked cruising. So we booked a cruise to Mexico. Since we were going out of port in LA, we decided to do one day in Disneyland!

I thought maybe, just maybe there was a chance. But then no. It wasn’t going to happen because I packed Dylan’s bag for that trip. And I thought I would know if he had been planning something. No one keeps secrets from me!

Our one day in Disneyland was going as perfect as any Disney day could go. We were rushing around the park trying to get as much in as we could. Dylan had been glued to his phone most of the day because Pokémon Go spots were everywhere and he was getting a lot of great catches.



We were right near the castle so I was like, “let’s get a photo!” And so we took this photo. But, no proposal. I knew if Dylan was going to propose obviously it would be in front of the castle. But nope. So yeah. Not happening.

We were headed towards the Matterhorn, and Dylan was like, “hold on go this way.” But he had his phone in hand so I knew we were making a Pokémon detour.

We were right by Snow White’s Wishing Well when out of nowhere he stopped, grabbed my hand, and started speaking all these sweet words. Dylan then dropped down on one knee. I instantly yelled “no way!” I couldn’t believe it.




Even though it had been something I had been waiting for, I still was just shocked. The ring was gorgeous, the moment was perfect, and it had happened. Dylan had proposed!

We of course immediately sent the photos above to our families. But then, we went and rode the Matterhorn. Because what else do you do after a Disney proposal?


Oh, and I also got many amazing shots of my ring around the park...


The rest of the day was just as wonderful. We were both so cheery and everything was just going well. We were actually in the parks during the time of Tower of Terror Late Checkout, which was where they were letting people ride the Tower of Terror in the complete darkness. A special thing they were having up until the ride closed. Anyways! While we were waiting in line the group of ladies in front of us bought us Tachos (tater tot nachos) as a engagement present! It was our first engagement gift, and such a sweet gesture. I'll never forget it!



Of course the very next day we set sail for our cruise. I honestly don’t think there’s any better way to celebrate an engagement than a seven day cruise to Mexico! But that morning before we boarded we stopped in Santa Monica and we wandered around on the pier. I was so overly obsessed with my ring! I don’t think I’ve ever shared these photos, but I kept taking photos of my ring against the water. Ah it was gorgeous!


It’s crazy to look back. I mean even if you can expect something, you’ll never realize how amazingly happy you can be once it happens. Dylan proposing made me happier than I could ever realize.

Thanks for reading a chapter of our love story! To see how this proposal turned into a beautiful wedding, check out all of our wedding posts.


#Disneyland #Disney #McAninchWedding

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