Isabelle only had one requirement when John proposed: she wanted to be surprised! John really pulled it off. In April, Isabelle broke her arm, which put her in a cast for 2 months. Seven weeks into the recovery, on May 24th, the doctor approved for Isabelle to take off the cast and to begin introducing "normal and routine activities" to build strength back in the arm. John encouraged Isabelle to go to a winery with him that weekend to celebrate no longer needing the cast and getting it off earlier than originally expected. The weekend prior to John proposing, Isabelle's brother Tim proposed to his then girlfriend, Madison. Additionally, Isabelle's bridesmaid Gabi said she thought her boyfriend Justin was going to propose (to trick Isabelle) and needed to get her nails done with friends. With just receiving the news she can take off the cast, her brother’s engagement the prior weekend, and thinking her best friend was getting engaged, Isabelle did not think John would propose that weekend. John proposed on May 27th, 2023 at the Hillsborough Vineyard in Purcelville, VA. John planned the proposal with a photographer and gathered our families and closest friends to travel and celebrate. It couldn't have been pulled off without the help of family and friends. It was a wonderful day of surprises and love.