Chris was living in Miami practicing law when Kaitlyn moved down in the fall of 2016 to begin graduate school at the University of Miami. Even though Chris was roommates with another student in Kaitlyn's program, they did not meet until nearly a year later in 2017 when they both attended a Memorial Day Weekend beach cookout. Chris asked Kaitlyn on their first date hours into meeting her and they have been inseparable ever since!

After asking both of Kaitlyn's parents for her hand in marriage, Chris decided to propose on a weekend when both his and her parents were planning on being in town for Disney's Food and Wine Festival. Chris was somehow able to keep ring shopping a secret, and Kaitlyn had no idea what was coming, so much so that the week before, she suggested Chris was "really missing a great opportunity to propose with everyone coming to town." Under the guise of a dinner reservation on the Boardwalk and pre-dinner drinks at the Yacht Club, Chris was able to get Kaitlyn out onto the dock and down to the boat launch to "take in the view." Suddenly, Chris pointed into the sky and said, "What's that?" When Kaitlyn turned around, Chris was on one knee, asking her to be his wife! After saying yes through lots of tears, both Kaitlyn's and Chris's parents came running down the dock. For a final surprise, Kaitlyn's sister and Maid of Honor Maggie had also come for the trip with Chris's brother Tommy flying in later that evening. A celebratory dinner at Flying Fish rounded out the evening with a full weekend of Disney fun with family and friends to follow.