Wake up with a Smile

Join our newsletter

Couple Accidentally Proposes To Each Other At The Same Time At Disneyland.

Google “Engagements at Disneyland” and see how many results pop up. Proposals happen every day at the Happiest Place on Earth.

20-year-old Jesse Tober decided to follow suit, and planned a proposal to her boyfriend, Kasey Donovan, in front of Cinderella’s castle.


Tober and Donovan, 24, have been dating since 2016 when Donovan randomly followed Tober on Twitter because her profile included lyrics to a Blink 182 song. The two got to know each other online and bonded over their shared love of Disney.

In August 2016, they took their relationship offline and met in person for the first time. Donovan flew across the country from California to upstate New York, Tober’s hometown, and visited Niagra Falls together. Soon enough, Tober flew to California and the two visited Disneyland for the first time together.


On August 20, 2018, Donovan and Tober ventured to Disneyland again. This time, Tober had plans to propose. She had started planning her proposal three months ago and told Cosmopolitan that she had picked out the ring “forever ago.” When they made their way to Cinderella’s castle, Tober was prepared and even had someone standing by to get a video of the occasion.

Unbeknownst to her, Donovan had the same plan.


Donovan had been planning his proposal for over a month, and even picked out a ring from the Enchanted Disney Jewelry Collection – because what is a Disneyland proposal without a gorgeous Disney-Inspired ring?!


Tober posted the video of the proposal on her Twitter and it’s about as cute as you’d expect. She was so confident when she opened the ring box to pop the question, and so confused when Donovan realized what she was doing and simply said, “really?” before laughing and revealing his own plan.

Tober told Cosmopolitan that it was the “happiest moment at the happiest place on earth!” She has also revealed that she and Donovan hope to have their wedding at Disney.


Since the video was posted 24 hours ago it has garnered hundreds of thousands of likes and shares. People are loving the story, the couples’ reactions to each other, and the visual proof of the true magic of Disney.

Check out the engagement video posted below – and don’t forget to share!

Share your story & inspire the world.
If you have an uplifting story we would love to hear about it! Share it with us here.

Want to be happier in just 5 minutes a day? Sign up for Morning Smile and join over 455,000+ people who start each day with good news.