Kaylee and Trenton met while in college at William Penn University. Trent liked Kaylee's photo on Facebook. Kaylee then liked Trent's photo. After doing that a couple of times, Trent finally messaged Kaylee saying, "You win." The couple started dating shortly after that and the rest is history.
Kaylee had a photoshoot planned with her best friends, Tessa and Bailey, in her hometown of Dubuque, IA. The photoshoot was to take place on a Saturday night. Trent and Kaylee drove up to Dubuque that morning, but before they left Oskaloosa, Kaylee noticed something. Trenton was very dressed up and was not supposed to be a part of the photoshoot. Kaylee asked Trent if he was going to propose today. Trent said "no" very fast and was taken back by how she knew. They drove up to Dubuque, not really mentioning much about a proposal at all. The photoshoot started and Kaylee was taking pictures with her friends. Out of nowhere, the photographer asked if Trent and Kaylee wanted to take any photos together, since it was a friends photoshoot after all. That is when it happened, Trenton got down on one knee and Kaylee said "Yes!" After the proposal, Kaylee stated that she knew it would happen because of the pants he was wearing.