Our Engagement Story

I’ve been wanting to write this post ever since my sweet Loss proposed but I figure with Valentine’s Day here, it’s the perfect time to share it. 


Loss and I knew that we were going to get married from early on in our relationship. We dated for a little less than two years and, when talking about the possibility of a proposal, I hinted that one at Disney World, my ultimate happy place, would be beyond amazing. It just so happened that in May of 2014 we went on a trip to the Happiest Place on Earth with my aunt and cousins with a proposal as the goal.

We were just babies doing Rapunzel & Flynn Rider costumes for Halloween 2013

Planning a trip to Disney involves a lot- money, planning, time off work, etc. So yes, while I knew we were going and Loss was going to propose (I knew the day too, since members of our family came down to help out with it), it was still as magical and special as if it’d been a full on surprise. I wasn’t sure how he was going to actually do the proposal, I just knew that my parents, his mom and sister and grandmother and my aunt and cousins we were staying with were taking part in the big day.

It was May 30, 2014 and we were at the Magic Kingdom (my favorite park) at rope drop. I met up with my parents for a few minutes- there was something magical about seeing them there in that happy place where we made memories growing up. My dad wasn’t as thrilled about trekking down to Orlando for the proposal at first, but I’m convinced being there that day made it worth it- plus they had such a blast getting to play, not having kids to keep up with, just riding the rides and taking it in as they wanted. Seeing how happy they were at the end of the day, it reminded me why you should marry someone you’re friends with, almost 30 years into the marriage.

My parents split off and I was on my own for a little bit. I hopped on the trolley down Main Street and was serenaded by the Dapper Dans all the way down to the Castle Court (that was pretty magical all in itself). Not long after arriving to the center of things, Loss showed up with his family and we meandered a little bit, taking a ride on the Mark Twain riverboat and a little bit later, Loss set off to get the proposal ready. Meg (sister in law) and I grabbed a Nutella waffle at Sleepy Hollow and got ready to start on the adventure.


Meg led me to the Carousel of Progress, where we found her mother, Vicky, waiting with a riddle and a charm for a necklace. After realizing, ‘oh wow, this is really happening, I’m going towards getting engaged now’, I read the riddle that answered which attraction to find next. I was super sweet, made me cry (spoiler: they all did) and each riddle talked about our past or future and linked to the attraction we were in front of. There was a charm with each stop as well, making reference to the riddle/area. It was all super in depth and meticulously though out.

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This one is probably one of my favorite photos of us together ever


Next up was my mom, Vicki (yes, two Vicki/ys!) in front of Small World. She handed me the riddle and charm and we both tried not to cry, knowing how special this moment really was. I’ve always been super tight with my mom and I can’t imagine what she was thinking as her first born was on her way to being engaged (and she probably didn’t know how much her sewing skills would be appreciated when it came time to hem my wedding dress!).


After my mom, we (Meg stayed with me the whole journey) found my dad, Jeff, in front of Haunted Mansion. As I mentioned before, he wasn’t as super stoked to travel down for this proposal, at first, but I know, in hindsight, he wouldn’t have had it any other way. I was certainly very thankful and appreciative that he and my mom made it a priority to be there for this big moment in mine and Loss’ relationship and life together (spoiler: I might be crying a little writing this).


From the Haunted Mansion and Dad, we moved along to Big Thunder Mountain (my favorite of any Disney roller coaster, by the way). At that stop was Loss’ grandmother, Shirley. Loss spent much of his childhood very close to Shirley and they are still close to this day. In getting to know his family, I also have spent much time with her and am glad that she was able to be there for our special day. You could tell she was so happy for us and that did nothing but put a smile on my face as well.


After seeing Shirley, the next to last stop was in front of Pirates of the Caribbean (if you know the spoke and wheel model that Disney World was built with, you’ll notice we’ve been going in a circular motion, from right to left). My aunt Gina and cousin Nolan met us and passed along the last riddle and charm. It was fun having them there and I know that Gina had been someone that Loss had picked her brain when planning the day. I really appreciated having them not only let us stay with them but helping make these magical moments happen.


From Pirates, it was on to the Partners Statue for my last stop. I knew what awaited me and if it hit earlier that ‘holy crap, he’s proposing’, this moment was it. It was going down.

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This photo stays on the wall at home, forever and always

And it happened, with Walt and Mickey, our loved ones and some families and groups getting photopass photos taken watching. It’s crazy because there are few moments in my life when a has faded away, but it happened here. Even with all these folks watching, I didn’t feel like anyone else was around. Loss spoke sweet words that I know he meant every syllable of and I said yes.


When the people around us started clapping and cheering, I was brought back to where we were. In front of Cinderella’s Castle, in my favorite place in the world where I had made so many memories in my life. It’s my place of escape from the crazy world and where I can always feel like a kid, regardless of how old I am. I can dance around and smile and sing along and cry with happiness. And by proposing right there, it showed that Loss not only recognized but respected and let me know that wasn’t the end: we would have more of those moments at the Magic Kingdom and beyond.



The sweetest thing happened after I said yes and I composed myself a bit: this sweet little girl who (I assume) had seen what was happening came over and gave me a big hug. She didn’t let got for a good minute. It was yet another magical little moment that wouldn’t have happened anywhere but Disney and it made everything even better.

Afterwards, we got some photos taken with our new ‘just engaged’ buttons around the castle. This was the day, if not before,that I truly saw how magical and amazing the Photopass crew can be, too. Loss talked to the photographer in front of the Partners statue before I showed up and let her know what was about to take place when I showed up. She was sweet and well trained enough to know to shoot away and we had so many photos loaded up on our My Disney Experience app not long after the proposal happened (not an ad, just sharing something that I love- I truly believe if you have a special trip/event happening when you’re going to be at Disney, Photopass is something you should invest in).


One of my most favorite photos of the day is the one of the whole crew that helped make the day possible, in front of the castle. Every time we visit Shirley, she has it framed in her guest room and it makes me smile and think of that sweet day.


After the proposal and some photos were done, we headed up to the Chapeau and I got the pair of ears I’d been dreaming of: a simple, classic pair with the words “Just Engaged” written on the back. We told the cast member what had just happened and she even gave us the embroidery for free and I put those ears on so happy. I had my man and my ears- I didn’t need anything else.

So this is love. ❤
Don’t worry, those ears were worn everyday the rest of the trip.

One fun thing that we did was get photos with some of my favorite characters and they would always ask about our ‘Just Engaged’ buttons. My favorite was Rapunzel (who also happens to be my favorite Disney character) and telling her all about how it happened. She was so sweet and animated and hung on every word. This is why I love Disney.



We also closed down the park, staying til close that night, enjoying all the time we could with our families. It was super fun to spend time with our loved ones who we don’t always get park time with.


I know this tale might sound a little crazy and out there for someone who isn’t a huge Disney nerd but it worked so beautifully for us. It meant so much and the fact we had our families travel down to spend the day with us, it was simply magical. That was almost 4 years ago now that Loss proposed and we spent our honeymoon in June 2015 at Walt Disney World as well. We haven’t gone back since then but it’s my goal to make that happen this year (or very early next year), so I’m working on it. I love knowing that anytime we go back to that magical spot in front of Walt, Mickey and the castle, it is where we had our special moment and promised forever. I know that this spot will be a place we return every visit and reminisce what happened that day in May 2014.

Thanks for letting me share our story- I knew I had to get it down, even if it’s just a few years later. My wish for you is that you have magical moments in your life, just like we did that one day, regardless of where you are.


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