Courtney and Keith's Disneyland Caricature Proposal

How We Met: My wonderful fiancé, Courtney, and I first met while we were in an Anthropology class together in Germany. During that first class period, we locked eyes and wanted to know more about each other. After a couple weeks passed, we decided a first date was in order. After that first date, we got along great and almost immediately fell in love with each other. I was getting ready to move back to the states due to the military, so I asked her to come with me. Four months after that first date, we packed our things and moved to Oklahoma.

how they asked: The years that followed were very special, and our relationship only got better. When I felt I was ready to propose to Courtney, I knew I had to do it in a unique and extraordinary way. It took me a few weeks to finally come up with the perfect proposal, and I wanted to do everything I could so that she wouldn’t suspect a thing. For that special moment to come together as I had hoped, I knew right away that I would need help from my parents. My mother and father love going to Disneyland, and have remained annual ticket holders for as long as I can remember. Courtney and I had been in our relationship over four years, so it was a matter of time before she adopted the love for all things Disney. A few times in the past she had even told me she would love to get engaged at Disneyland.

Several months before we were set to leave on our trip, I called my father and let him in on my plan to propose to Courtney while we were at Disney, and that I wanted him involved. He was overjoyed and couldn’t wait until the big day! When December rolled around, I hid the ring deep in my suitcase so she wouldn’t be able to find it, and then we were on our way to California! Upon arrival, I snuck the ring to my father because I knew there was a chance Courtney may look for it. Fortunately I did, because there was a moment when she checked my pockets! Because we were at Disneyland, she had high hopes that I would “pop the big question”. To get her mind off of the idea, I continuously told her that we would look at rings when we arrived back in Oklahoma. I had to do whatever I could to throw her off of the scent! I even tricked her at the end of our first night in Disneyland. We were at the park standing in front of the beautifully lit Sleeping Beauty Castle, when I grabbed her hand and said “Courtney, we had a wonderful day and are standing in front of this gorgeous castle, so I would like to give you something.” She turned to me with a somewhat confused, but excited look on her face. I reached into my pocket and handed her a Disneyland collector’s pin that I had been given earlier. She was angry with me, but we laughed about it. I explained that I had only fooled her because she would not stop pestering me about a “proposal.”

The next morning (the big day), she no longer had engagements on her mind. As we walked through the Disneyland entrance gate, I pointed out a caricature booth and asked what she thought about them. She had really liked them, and I acted as though I thought they were dumb. My parents overheard us talking and encouraged us to get a portrait done. We quickly went over to the caricature booth to schedule an appointment for a later time. Little did she know that this was where I planned to propose. My mother and father already knew about my secret plan, so as they were setting up the appointment they whispered to the artist that I wanted to propose in the illustration she was to draw. Courtney and I stood about ten feet away from my parents as they talked with the artist. While we waited I tried to talk Courtney out of wanting a caricature done because I felt they were tacky. Again, this was all a ploy to get her from getting any ideas or assuming anything. Our appointment was set for the evening, so we immediately went for the rides and attractions. Four o’clock finally rolled around, and we went up to the booth to get our picture done. We sat down and our artist, Kim, began illustrating our coupled portrait. Several people started circling around Kim as she drew us. I was beginning to get nervous as some children gleamed at the photo. I didn’t want anyone to ruin my plan. Luckily there was a large sign that we were unable to see, that read “Shhh! Proposal in Progress”. As she finished the last little details of our portrait, I noticed the several people standing around the artist had multiplied to about fifty people. I was very nervous with this big crowd watching.

Image 1 of Courtney and Keith's Disneyland Caricature Proposal

Finally, Kim stood up and turned the photo around for Courtney and I to see. It was a large illustration of me kneeling on one knee in front of Courtney with a large ring in my hand, and a quotation bubble that read, “Will you marry me?” Courtney turned to me with a big smile, assuming that the artist was giving me a hard time, and asked why she drew that. As she turned and looked toward me, I got on one knee and said, “Courtney. We have been together for over four years, and I could not see myself living without you. I love you so much. Will you marry me?” She immediately started crying and said “yes!”. Seeing her so emotionally happy brought tears to my eyes as well. The large crowd was clapping, cheering, and some were even crying as well.

I know it’s cliché, but the moment really was magical!

Image 4 of Courtney and Keith's Disneyland Caricature Proposal

Image 2 of Courtney and Keith's Disneyland Caricature Proposal

Image 3 of Courtney and Keith's Disneyland Caricature Proposal