Much like most other millennial couples you know, Caitlin & Jack met on a dating app in February 2018. Although the two didn't know each other during their overlapping time at Miami University, they quickly bonded over a shared love for the school, their many mutual friends and Chicago.

After messaging for a couple weeks, Jack & Caitlin went out with friends for drinks and dancing at Stanley's Lincoln Park, located just around the corner from Caitlin's first Chicago apartment. They consider this night to be the start of their love story when they knew there was something special there. The following week, Jack swept Caitlin off her feet with a first official date to see Hamilton in downtown Chicago. For weeks afterward, Caitlin would recount this first date to friends and family, remembering fondly the moment they laughed so hard at the theatre that Jack spilled champagne all over Caitlin's lap. As far as first dates go, this was one to remember.

The weekend of July 28, 2023 started like any other. Caitlin & Jack had plans to lay low on Friday night before grabbing brunch with friends on Saturday morning. When it came time to choose a movie Friday night, a historically difficult task for Jack & Caitlin, Caitlin was thrilled when Jack included Hamilton in the list of movie options for her to choose from. It had been quite some time since they'd last seen the play/movie, so they watched and sang and reminisced about that first date more than five years prior.

The next day, Jack & Caitlin made their way to Lincoln Park for brunch. The plan was to meet the other couple at Cafe Brauer, a restaurant located just outside Lincoln Park Zoo. As they neared their destination, Jack took Caitlin on a detour to the nearby Lincoln Park Nature Boardwalk, a place Caitlin loved and frequented during her three years living in Lincoln Park at the start of their relationship. There on the boardwalk, just steps away from Stanley's Lincoln Park (where it all began) and Caitlin's first apartment in the neighborhood where they fell in love, Jack asked Caitlin to marry him.