Jimmy and Anna Grace met on the dating app Bumble (#SwipeRight) and had their first date on March 2, 2018. Upon meeting, they realized that they had several mutual friends and grew up a couple of miles away from each other in Indianapolis. Anna Grace had even been to parties at the Kennedy house throughout the high school and college years! They also realized that they had both lived in Chicago at the same time, and lived close to each other during that time, too. After unknowingly crossing paths numerous times over the years, it was great to finally meet! :)

Jimmy and Anna Grace got engaged on July 5, 2019. The 4th of July is one of AG's favorite holidays but she had to work the 4th so they planned on going to the lake on the 5th. Jimmy came home from work around 2 PM that day and they loaded the car and left. After stopping for gas near their house, Jimmy said that he forgot a case of beer he bought for the lake and headed back to their house to get it. AG waited in the car and a minute later Jimmy came out and said he spilled the beer and asked if she could come inside to help clean up the broken glass. They walked inside and AG saw no spilled beer. She followed Jimmy to the back deck, where a gorgeous floral arrangement and champagne was waiting and the next 5 minutes is a happy blur! Family came over and then we celebrated all night with family and close friends. It was a perfect day!