Kyle proposed to Emily on their cruise in March 2024. The proposal itself, however, did not occur without a few hiccups thrown Kyle's way. The original cruise itinerary included three stops - one in Key West, Florida, another in Cozumel, Mexico, and a final stop in Great Stirrup Cay, Bahamas. When Kyle booked the cruise, he had originally envisioned proposing to Emily at their first stop in Key West. However, shortly after departing from the Miami cruise terminal, an announcement was made that storm was heading for Key West and the boat would be unable to dock. The stop in Key West was cancelled altogether as the boat continued on course to Cozumel.

Finally, after being onboard for two full days, the ship docked in Cozumel. Eager to get off the boat, Kyle and Emily got dressed and ready to disembark. Upon opening their door to leave, they saw that a note had been slipped in their doorframe stating that due to weather conditions, their planned, onshore boat tour excursion had been cancelled.

Fast forward to day 4, another announcement was made again that due to inclement weather, the cruise was being diverted from its final planned stop in Great Stirrup Cay, Bahamas to Costa Maya, Mexico. Eager to make their last stop count, Kyle and Emily headed to the excursion desk on the ship. Unfortunately, other passengers had beat them to it, taking up all the slots on the excursions that they wanted. Being left with limited options, they settled on a beach excursion that took them to a different part of the island. Upon arriving in Costa Maya, they were greeted with a beautiful beach full of lounge chairs, and shade canopies. Kyle wasted no time and after each finishing a margarita, he asked Emily if she wanted to go for a walk up the beach to explore. They eventually reached a secluded spot on the beach, surrounded by palm trees and crystal clear water. Kyle got down on one knee and asked Emily to marry him, and of course she said yes!