Highlights Along the Way
Family Travel, Treats, Tips, & Traditions

That time some lady stole my free trip to Walt Disney World and why it is totally OK now.


Ever since I was a little girl I have wanted to travel to Walt Disney World, especially Disney’s Magic Kingdom.  To say I was a Disney Nerd as a kid would be putting it mildly.  As a kid I loved art, specifically animation, and more specifically Disney Animation.  I loved Walt Disney’s story, his innovations, his movies, Disneyland Park, and all that it stood for.  My family growing up provided us with all we ever needed, and pretty much everything we wanted – but a Walt Disney World vacation was out of the question, we just couldn’t afford it.  The following is a bittersweet tale of how I didn’t win a trip to Disney World.

cinderellas castle

I remember our little SoCal city once held a promotional giveaway for an all expenses paid trip to Walt Disney World – airfare, tickets, hotel, and spending money.  Dozens of businesses participated and you had to go into at least one business and fill out a form – you could go into as many businesses as you wanted.

cinderella's castle

You guys, at 12 years old I filled out over 100 forms, every single business that had a drop box I filled it out.  Some of the drop boxes had 0 entries when I went in the day before the drawing.  I went to bed that night knowing I had done all the hard work, it was going to happen. There was not one person in that little town that loved Disney as much as me, there obviously was not one person that had as much sticktoitiveness to fill out every single form.  I wasn’t raised in a family that called on divine intervention, but I called on that too.

tomorrowland speedway

It still pains me some 20+ years later to inform you that some lady who was entered by her adult son in one store on a whim won that contest. You read that right, I didn’t win, some lady who didn’t even fill out one form and didn’t know about the contest won.  She was all “Oh, what? I don’t even care but I suppose I will take it. Whateves.”

people mover

Not winning that contest was like the worst of the world. Our family never got on planes, we didn’t do big gigantic trips. *queue dramatic weepy sad music* Door was closed. I knew it was my only shot at Walt Disney World and someone who didn’t even care just straight up stole it from me.  I was so jealous of that lady.  I had no idea who she was, but she was the worst. That lady just went to Disney World all like “I don’t even care that Kate wants this more than me.”  She probably even complained at some point during her trip – can you imagine?


I was the perfect winner and somehow the Universe had failed me. Just writing this makes me want to find some sort of 4th dimension so I can go back, hug that really upset 12 year old and let her know that she gets to go, it’s just gonna be a little longer.

fantasy land

All that to say, while I have grown to appreciate more than just Disney over the decades – Walt Disney World holds a special place in my heart.  When we were invited to the Disney Social Media Moms Celebration I am not ashamed to say there was a little bit of healing for that 12 year old girl.

roller coaster

While this trip wasn’t free (like the one that lady stole from a child all those years ago), it was a conference that gave our tight budget family the opportunity to go to Walt Disney World – and we spent the better part of two days at Disney’s Magic Kingdom Park!  Hear that 12 year old Kate?  You don’t get to go until you are super old (30s), but you get to go to Walt Disney World!


I sure wish that lady would have taken me along with her back in the 90s, but it’s OK.  I got to experience Disney’s Magic Kingdom for the first time with a whole bunch of other first timers that I love so much.  My husband had never been to Walt Disney World either – and this was our first big trip as a family of five.  Our big kids can’t even remember the last time they were on a plane and little Miss C took her very first plane ride to Walt Disney World – not a bad destination if you ask them!

small world

So, to the lady who didn’t even know me that I harbored bitterness toward all these years…. you’ll be happy to know I have forgiven you.  I didn’t win a trip to Disney World, but it is OK. We should probably compare photo albums someday.








I didn’t win a trip to Disney World and my little heart was broken…. but I know now, there was a very good reason why!  Something sweeter was around the corner!

Until Next Time ~ Kate
Categories:  Disney, Disney Parks
  1. Love this post! At 35, I relate to your 12 year old self. My Disney obsession border lines medical help. From tattoos to naming my daughter Alice, Disney finds its way into every crevasse of my life, so when I see others who are (in my eyes) less worthy of winning trips(or being called to DSMM conference, present company excluded of course) I feel a pain, but as you were able to amend for it, I too hope the universe and some Disney Magic evens it out for me (and my family, but mostly me!) 🙂

    • kate says:

      Oh Michelle – I don’t know you but I hope you get to attend some day too =) I wanted to go for several years before getting my first invite last year – I say just keep growing and support other Disney bloggers – follow and respond to the hashtags – sign up for the “On the Road” events and if you are selected for that you get to shake hands with and learn from so many amazing people from Disney! I wish you well!

  2. Sabrina Paul says:

    Great story Kate!!! I am sure 12 year old Kate is all about happy endings, no matter how long it takes to get there 🙂 and something tells me that you will go back to Disney World again someday!! I too am a crazy Disney nerd!! I have been a single mom for many years and an Orlando trip is not on the horizon anytime soon, but I did recently get my son and I DL annual passes! This was a dream come true for me!!! :’)

  3. Sarah says:

    Is this satire?

  4. Settle a bet for me – this is tongue in cheek, right? A humor post?

    I’m so glad you had a great time and I LOVE the pictures!

    • kate says:

      Amy – I did enter a contest at 12 years old where I filled out all the entry forms and some random lady who didnt even know she was entered won and as a 12 year old I was SUPER jealous- I don’t really hold any ill will towards her 😉

      • Thank you for restoring my faith in humanity! I can relate to the devastated little kid. And to the snarky adult writer 😉

        • kate says:

          Haha! I think we all have that ‘oh man, the world has caved in’ moment as a kid that is really not the end of the world but we still remember that pain years later….we were taught that disappointment helps build our character…. I think it is what developed the snark 😉

  5. Kayla says:

    These pictures are KILLNG me. My family is usually taking a trip to the World around this time, and I’m usually double checking reservation times and re-arranging fastpasses right about now. We’re going in December this year instead, but GAH! It still hurts that it’s getting warm out and I’m not packing for Port Orleans! I’m so glad you finally got to enjoy the magic!

    • kate says:

      Awww! You will be there soon enough! If you have never been to Disney during the holidays you are in for a treat! It will be worth the wait!

  6. Jaime says:

    These are awesome pictures! I can’t even imagine the anger you felt as a kid; I’m glad you were finally able to go, haha. =)

    • kate says:

      I was so scowly for quite some time after that lady won – LOL – but I sure love these first photos too! Thank you for reading!

  7. Donna says:

    So cute 🙂 I am glad you got to go in the end! Looks like you had a fantastic time with your little family!

  8. Glad it all worked out in the end! You probably had as much fun going with your kids as you would have as a kid. 🙂

  9. Rachel G says:

    I loved the drama of the story you told, though you had to wait way too long for your happy ending. I ‘finally’ got to go to Disney for the first time last year–my parents were meeting up with my uncle and aunt and they were bringing all the kids…I am no longer really one of the ‘kids’ since my siblings and cousins are all much younger than I and I have a husband of my own…but I asked if I could join in the trip with them, heartlessly left my husband at home since he had to work, and had a grand time visiting Disney at the age of 22. Now I’m hooked.

  10. Carissa J. says:

    Hahaha…this makes me laugh. Though, to be sure, if it was 12-year old me, I, too, would be one unhappy camper scarred for life. 😉

  11. Christina Dominguez says:

    That is a very neat story and I can relate because growing up I dreamed and dreamed of going to Disney but that wasn’t a possibility due to money. So, when I was 29 and I took my family to Disney World I don’t know who was more excited, my kids or me! 🙂

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