Caleb took Jaden by complete surprise when he proposed. He began his plan in October 2025 after speaking with her parents, slowly letting family members know as time went on. Caleb worked closely with the owner of the Preacher's Son and staff at Crystal Bridges to ensure the proposal was perfect. A week before the proposal, he told Jaden of their plan to visit Crystal Bridges and then eat dinner at the Preacher's Son to celebrate Caleb's graduation and new job. She thought how this would be the perfect time to propose with his family coming into town soon, but convinced herself it was not happening. Jaden was so clueless that her dad handed the ring to Caleb while at Nona's for a family event. Thursday night finally came and after walking through the gallery, Caleb got down on one knee and asked Jaden to marry him. Of course she said yes!