Olivia and Josh

How We Met

Josh and I met in Mrs. Bays’ 7th grade honors math class. I sat behind Josh alphabetically, and we talked every day. Josh constantly stole my shoes off of my feet when we were sitting in class , although I never put up much of a fight, I was just happy that he noticed me! Our relationship began to grow from flirty in-class banter and shoe stealing to phone calls every night lasting for hours. We talked about anything and everything, until our moms made us hang up to go to bed, but we would still text until we both feel asleep. In high school, we continued to talk, but dated other people, never letting each other knew how we felt. Every time I would date someone, Josh would send me a text or call me, or show me any sort of attention, and I would immediately end the relationship in hopes that something would start between Josh and I! That’s exactly what he wanted, but he had the mentality of “I don’t want you yet, but I don’t want anyone else to have you either!” Our senior year of high school, time was winding down and we weren’t sure what the future held for our relationship. In December 2011, Josh finally caved and asked me to the basketball homecoming dance.

Wedding Proposal Ideas in The Magic Kingdom at Walt Disney World

Engagement Proposal Ideas in The Magic Kingdom at Walt Disney World

I had been waiting for that day for so long, I was absolutely thrilled, and I later found out that Josh felt the same way. That same month, on December 23, we went on our first official date, which was raccoon hunting in the woods behind my house. He should’ve known from the start I was crazy about him, because that was the last thing I would ever do! We started officially dating on February 6, 2012, and we became inseparable. Josh went with my family on a cruise that April over our spring break, where Josh told me he loved me during a late night talk on the ship. We couldn’t be happier, but as graduation approached we were faced with the harsh reality that we would be going to different colleges 3 hours apart in the fall. When school started, we both took every opportunity to visit, and saw each other as often as possible. My mom drove me 3 hours almost every other weekend so that we could visit! Our sophomore year of college, Josh transferred to my school and we saw each other every day! We had every meal, class and free second together, and everything was perfect.

Olivia's Proposal in The Magic Kingdom at Walt Disney World

Marriage Proposal Ideas in The Magic Kingdom at Walt Disney World

Even when we went back home for the weekend, we still made time to see each other. We found out our senior year that we got into different professional schools, and once again, as graduation approached, we were faced with a long distance relationship, with me going 2 hours away for medical school while Josh was staying home for pharmacy school. That summer we didn’t waste any opportunity to see each other, yet again, but this time, leaving seemed so much harder because we had grown used to seeing each other so often. Josh and I went on one final vacation with my family before school started, where Josh surprised me with not only a trip to Disney World, but a proposal in front of Cinderella’s Castle. It was more than I ever imagined! Josh and I went from shy middle schoolers that tried to flirt, to high school students that were afraid of commitment, to college students falling had over heels for each other, and now the days are winding down until we say “I do!”

How He Asked

To begin our story, my parents got Josh and I a cruise for our college graduation. On the trip, we would visit one of my favorite places in the world, the U.S. Virgin Islands, and I was excited to share this amazing place with Josh! Josh, knowing this place was very special place for me, concocted a plan to make the trip even more special. While there, Josh snuck away while I was shopping, and found a jewelry store! After looking at several rings, Josh found “the one” but couldn’t purchase it without one thing- my daddy’s permission! Josh called my dad from the USVI to ask his permission to propose.

With his permission, Josh went back to the store and purchased the perfect ring, and returned to find me still shopping, and clueless as to what just happened! Josh hid the ring for the rest of the trip, and I still had no idea. The Story continues three months later when, Josh, my parents and I went on a trip to Treasure Island, FL. I was upset that I wouldn’t be going to Disney world, because I had been every year, but I didn’t let it affect my trip because I wanted to enjoy my time with family before I moved away for medical school. One night, my dad pulled me to the side, telling me that we were going to Disney the next day! I was so surprised and excited, but was totally blind as to the reason we were going! The next day, on July 18, 2016, we arrived at the Magic Kingdom.

Going through the bag check, I noticed that Josh ended up ahead of me, but I thought nothing of it. Come to find out, he couldn’t let me discover the contents of his bag! We rode some of our favorite rides, and at lunch time, Josh and I separated from my parents to eat at different places. Josh and I got our lunch and were waiting for my parents, who seemed to be taking forever, but they weren’t eating at all, they were planning out the most magical proposal! They finally called Josh to let him know where they were, and we set off to find them. As we were walking across the bridge in front of the castle, I noticed a white box sitting on a bench. Josh said “Why don’t you go open that?” and I didn’t want to because it wasn’t mine but after some convincing, I opened the box to find a pair of Mickey ears that read “Will you marry me?”.

I turned around to see Josh on one knee holding a ring box. I couldn’t contain my excitement as I said “YES” and put the ring on my finger!! It was more than I ever hoped for, from the man I have always loved. There was a photographer there that captured every moment, and the rest of the day was truly magical! We had lunch in Belle’s Castle, had free snacks all day, and a free Christmas tree ornament to celebrate the occasion!!

The proposal consisted of a ring from my favorite vacation spot, while on a surprise trip to my happiest place, while on a vacation to Treasure Island, which I consider my second home! To say the day involved everything I loved would be a major understatement! The day was truly the happiest day at the happiest place on earth!

Our Video

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Special Thanks

Kelli Lynn Photography
Photographer