After meeting at a bar and playing reverse cash cab in a shared Uber ride home to Miami from Ft Lauderdale, Missy insisted Kyle come up and hang out with them. At the end of the night she insisted Kyle get Chrissy's number and the rest is history.
After a few audibles, a lot of help from Chrissy's family, a poor innocent berated receptionist at Barry's, and a passed out trumpet player, Kyle proposed at home in the new house they had just bought together. Knowing that Chrissy is a "morning person" he was able to catch her off guard and at her best. MacGyver, man's best man, was there by Kyle's side in his tuxedo the whole time. Although not to MacGyver's liking, he planned to have a jazz band pop out of the bushes and play "All You Need is Love" as in the movie Love Actually, one of Chrissy's favorites.