Kailyn and Kyle

Wedding Proposal Ideas in Magic Kingdom at Disney World

How We Met

Kyle and I met New Years’ Eve 2015 through mutual friends at the time. I had seen him from across the room and questioned who he was and was introduced to him as “Dinny”. The first thought that ran through my head was, “What kind of name is Dinny?!”. Luckily, I learned it was a nickname that his buddies had given him and that his name was Kyle. Me, being the awkward human I am, asked him if I could pinch his cheeks…. (I’m really not crazy, please refer to how pinchable his cheeks looked in the attached photos!!). He looked at me like I had 85 heads and responded with “Uh, no?” and that was the end of that conversation. I automatically assumed that I blew it, that he thought I was insane and that we would never see each other again that night.

Marriage Proposal Ideas in Magic Kingdom at Disney World

The countdown had finally come around, I kissed a bottle of champagne and Kyle tells me he kissed a bottle of beer and everyone proceeded to dance, hangout, etc. Later that night while I was dancing around with some of my friends, I felt a hand grab mine and tug me towards them. Lo and behold, it was Kyle!! He asked me to dance and of course, I said yes (I was also internally screaming because this was my second chance and I didn’t want to blow it!). We danced and drank and before I knew it we were upstairs, away from the party, talking for 4 hours about everything and anything under the sun. We talked about how both of our families have the letter “K” for first names, what color our countertops were going to be in our future house and how we were going to have an inground hot tub and a golf course in our backyard. It was amazing how easy it was to talk to Kyle and how natural it was to talk about our future house (!!!) after knowing each other for just 1 night!

Where to Propose in Magic Kingdom at Disney World

We ended up exchanging numbers and I put my contact name in his phone as “Kailyn My Future Wife” with every heart and kissy emoji on iPhones at that time. Little did we both know that I would actually be his future wife!!!!! I still joke about how lucky I am that I didn’t scare him away that night, while he jokes that he didn’t have a pillow and a blanket and I did, so he had stuck with me so he could sleep comfortably that night *face smack emoji*. We shared our first kiss that night and slept as comfortably as we could on a floor with like 4 other people, so safe to say it was as magical as it could get. We didn’t end up seeing each other that next morning (he claims I ran away from him while I claim the same thing LOL) but we had just left the room that morning at different times and never ended up seeing each other again. Later that day, I was texting my friend freaking out that I wanted to text him but was so worried I’d be coming off at clingy, but funny enough he was texting her the same things I was! We ended up texting each other, clearing up that we weren’t running away from each other that morning and the rest is history!!! New Year 2020 is going to be our SIXTH New Years together (!!!) and is definitely one of our favorite holidays to celebrate together.

How They Asked

Kyle is a golf professional at a country club and plays in a tournament in Port St. Lucie, Florida each winter. He had called me in October and asked if I wanted to fly down to Port St. Lucie for 4 days this year, watch him play in his last tournament and then head to Disney World for 3 days before coming back home. Kyle knows how much I love Disney and how I’ve been wanting to head back there so I was SO excited and immediately started planning our trip with him. We had picked out where we were going to stay, our fast passes, food, everything! It was Kyle’s first time and my third, so I was super eager to show him the MAGIC that is Disney World!

When we got to Disney after Kyle’s tournament, I kept thinking that a proposal was coming on this trip or at New Year’s Eve. I was trying to not get my hopes up but I couldn’t help but long for a Disney proposal in front of Cinderella’s Castle! We started out our Disney adventure at Epcot to drink around the world showcase. We had all the drinks, all the food, and were exhausted by the end of the day! We had planned the Magic Kingdom for the next day and I was really worried that we weren’t going to be able to make it through the whole day because we were both beats. We woke up that morning and I was unusually nervous because I was thinking that today may or may not be the day that Kyle asks me to marry him. I told him the night prior that I wanted to get a picture in front of Cinderella’s Castle the moment we get into the park because those PhotoPass lines can get kinda crazy during the midday. He was all for it and was giving me full control of the day, so I figured that it wasn’t going to be happening this trip since I was essentially calling the shots. I thought if he was going to be proposing he would have been telling me where we’ll be going at that time but that was not the case at all. While we were taking the ferryboat over to the Magic Kingdom, I was internally battling my feelings and trying to keep myself from becoming sad that this wasn’t going to be the day and Kyle was secretly holding my BEAUTIFUL ring in his bag and showing NO signs of nervousness or anxiousness.

When we got into the park, we stopped to watch the parade that was going on and then made our way to Main Street after the parade crowds had cleared. I introduced him to the most magical view in the Magic Kingdom and was so excited to get a picture in front of the castle. We found the first PhotoPass photographer (I so WISH I could remember his name because he was absolutely amazing) and waited in line to get our photo. When it was our turn, we put our backpacks down and I went to go stand to pose for the picture. I went to put my arm around Kyle when he said that he needed to stop me for a second because he had to do something. I remember screaming “Oh my god, no!!!!” and then completely blacked out from pure shock and happiness! I didn’t hear a word that came out of Kyle’s mouth because I was too busy thinking “IT’S HAPPENING, IT’S HAPPENING” and I eventually saw him get down on one knee and heard him ask “Will you marry me?”. I shook my head yes but never got the words out because I was crying and couldn’t form any actual sentences. After he put the ring on my finger, I looked up and there was a whole crowd cheering for us! We had people coming up to us with videos and pictures they had taken for us, congratulating us, hugging us, everything. It made us feel SO special while surrounded by people we don’t know, so we couldn’t wait to tell our families. We took some pictures post-engagement, but as you can see I was still hysterical and had NO clue how to process everything that just happened!

Getting engaged to the love of my life in Disney was by far the most special, magical and exciting moment of my life and I can’t thank Kyle enough for all of his hard work and planning that he did to make this amazing moment happen. We now have a place where we can bring our kids and our grandkids to show them where our forever started and that is absolutely everything that I could ever ask for our proposal!