Jon and Kelsey were set up in October of 2014 by Lynn Doty! She is a family friend of the Hunters and a colleague of Jon from Otis Elevator. She gave Kelsey his number and a few weeks later Kelsey finally worked up the courage to set up a date... by this time Jon forgot he agreed to be set up. They were set to meet up at a restaurant near Kelsey's office. Kelsey arrived a few minutes early to find out the restaurant was closed or more technically shut down. A last minute text to meet at Classics, a local sports dive bar, changed the first date location! For the first few months of dating Kelsey's luck with restaurants did not change, as she somehow managed to pick two additional date locations that were similarly shut down. Jon now picks the restaurants!

Jon and Kelsey got engaged while on vacation with Jon's family in the Bahamas at the Atlantis Resort. Jon took Kelsey to dinner at Joe Andres' Fish, where they had a wonderful meal and walked the beach at sunset. Jon proposed at a beautiful secluded location on the beach! Jon's memories of this evening consist of the meal which included a full lobster, conch fritters, and a caramelized cream banana with mojito lime sorbet. Kelsey realized something was fishy when she accidentally felt the ring in his pocket while they were waiting to be seated at the restaurant. Needless to say they have different memories of the evening but still share the most important event, agreeing to spend the rest of their lives together!