Carissa and Steven

Proposal Ideas Walt Disney World

How We Met

I had already been working at Old Navy for about a year when Steven was hired for the holiday season. It was Black Friday and I was assigned to the fitting room. My friend and I were busy folding clothes and hanging them on racks this way when the store closed they could quickly be put away and we could leave. While I was talking to my friend, these two guys kept coming in to the fitting room to procrastinate and “hide” from their work (they weren’t the greatest of workers). I introduced myself to them and being the annoying person that I am, I began to ask them the most random of questions (what’s your favorite color, what do you do, do you like cupcakes, do you have a car, what’s your favorite christmas song, etc.) That’s how it all began. We continued to talk and found out we had a lot in common. We loved country music, being outdoors, trucks, Disney, etc. One thing I always wanted to do was to go mudding and off-roading and he promised to take me. After work, he asked if I wanted to go see his truck which was in the parking lot. I agreed, so we went across the parking lot and I hopped in. Being the nosey person that I am, I went through his things, turned on the radio, looked around, etc. I tried to see if there were any signs of him having a girlfriend (there wasn’t). I was impressed. He asked for my phone number in case we needed to exchange shifts and that was it. I hopped in my car and headed home, not expecting to hear from him. To my surprise, I got a text the next morning from Steven asking if I had slept well and if I wanted to go off-roading with him the next day. I agreed. So, the next day, we went off-roading and out to breakfast…. which then turned in to me meeting the family, moving furniture, buying the family christmas tree, and going out to dinner. From then on we were inseparable!

How He Asked

I was hoping that Steven would propose during our next trip to Disney World. I am a huge Disney-nerd and always dreamed of my proposal taking place in Magic Kingdom. We booked a trip during New Year’s Eve and I thought that this would be the most magical time to propose. So, I dropped hints. Lots of them. We looked at rings, talked about our wedding, and I even sent him thousands of youtube videos of Disney World proposals. I made sure he knew what I wanted. Although we talked about getting engaged, I wasn’t 100% sure he would propose. He was giving mixed signals. Once we landed in Disney on Friday, December 30, I knew it was going to happen. I just didn’t know when or how. Steven was acting strange and kept asking me questions about how much I loved him, if I really saw a future with him, etc. He never asked questions like that. We spent our first day shopping in Disney Springs and looking at all the Christmas decorations in the hotels. I grew excited as the day went on, knowing that the next day we would be in Magic Kingdom.

We got to Magic Kingdom before the park opened so that we could see the opening show (one of my favorites). The second we got inside the park I knew that he would be proposing and how he would be doing it. The first thing we always do when we visit the parks is take a picture in front of Cinderella’s Castle. Well, he wouldn’t even let me near the castle. We just kept walking right down Main Street and straight into Fantasy Land. Throughout the day I kept asking Steven when we could take a picture in front of the castle and he kept coming up with some excuse as to why we couldn’t do it. When he did say, “Ok, let’s go take our picture” he would chicken out. We would get to the castle, but then he’d find some excuse to leave. Either he wanted to look in a gift shop, go to the bathroom, get food, take a picture after the next parade, etc. Before I knew it, it was 5:00pm and we still hadn’t taken our picture and I was getting annoyed. At this point, all I wanted was my picture. The sun would be going down soon, and I wouldn’t get my picture with the blue sky in the background.

Finally, after what seemed like forever, he agreed to take a picture in front of the castle. We got in line for one of the Photo Pass people so that they could take our photo, and I was keeping my fingers crossed that he wouldn’t chicken out again. A parade and castle show was about to begin, so Main Street was super crowded. Thousands of people were sitting on the curb and walking on the sidewalks waiting for it to begin. Knowing what was about to happen, I began to get nervous because so many people would be watching. I don’t do well being the center of attention. After taking some photos with my phone, the photo pass person picked up her camera. I turned to Steven and said, “Let’s take a kiss picture!”. That’s when he responded, “Sure, but after I do this.” He got down on one knee and everyone on Main Street began to clap and cheer. I don’t remember anything that happened after that, but according to Steven all I could say was “Oh my God, I hate you” and I cried. He put the ring on my finger, we kissed, and then went to dinner inside Cinderella’s Castle to celebrate.

Carissa's Proposal in Walt Disney World