We were so excited when John first reached out to us about his plan to propose to his girlfriend, Cassie. They were going to be visiting Kentucky and staying at the Kentucky Castle in Versailles, KY. John and Cassie met on Tinder. John sent her a message with a cheesy pickup line about how he wished he could say Cassie had a great personality, but he, unfortunately, didn’t know her yet. Cassie thought it was sweet, and clearly, it worked! Their first date was in downtown Naperville, Illinois. Cassie and John met at a bookstore, then grabbed ice cream at a cute little place with an arcade in the back. Cassie beat him at darts despite never having played before. To this day, John claims it was beginners’ luck, but she’s beaten him since then, so she’s not so sure. They ended the evening at a coffee shop before John walked Cassie back to her car. When they got to Cassie’s car, they leaned in to kiss each other, but they both went the wrong way and ended up kissing each other right on the corner of their mouths. It was the most adorably awkward first kiss. John and Cassie are foodies, so they love going out to eat together. They also love going to the gym and lifting weights together, seeing movies, and hanging out with their cat.


John knew he wanted to spend the rest of his life with Cassie. So he decided he would propose on their trip to Kentucky. They were staying at the Kentucky Castle in Versailles, Kentucky. On a Tuesday night, Cassie and John had dinner reservations at 7:30. He told her he wanted to take some pictures before dinner and that they had to be ready at 5:00. Cassie didn’t think much of the big gap between pictures and dinner because John had told her there was another event at the Castle, and the concierge wouldn’t be able to take photos of them during that time. So at 5:00, when they were both ready, Cassie and John went out front, and the concierge took a couple of quick pictures of them before going back inside. John started talking about how special their trip and been so far and how much he loved her, and then suddenly, he was down on one knee, asking Cassie to marry him. Cassie said yes (while crying, of course), and after he put the ring on and they hugged and kissed. John said he had one more surprise for her. The surprise turned out to be us (Kevin and Anna), who had been secretly taking photos of their proposal. We celebrated by taking photos around the Kentucky Castle and also at Keeneland Racetrack. It was such a joy to capture Cassie and John’s proposal. They are both the sweetest, and we can tell just how perfect they are for each other. Congratulations, you two! We hope you have a lifetime of love, happiness, and adventure.

Proposal Location: The Kentucky Castle

https://www.thekentuckycastle.com/

Second Photo Location: Keeneland Racetrack

https://www.keeneland.com/

Engagement Ring: Jared

https://www.jared.com/

Proposal and Engagement Photos by: Kevin and Anna Photography

https://kevinandannaweddings.com/