Sherilyn and Josh met in the fall of 2006 in high school and dated for 2.5 years. They parted ways before Sherilyn went off to college. In the fall of 2016, they reconnected and have been together since. In the last 5 years, they have moved to Chicago, adopted their pup (Chase), and supported each other throughout this pandemic.

In September 2019, Sherilyn and Josh were on a day trip to Versailles as part of a trip to Paris with Josh's family. After lunch, Sherilyn and Josh decided to rent a row boat. After taking a rest from rowing, Josh literally rocked the boat by trying to get down on a knee. Forgoing that, he asked Sherilyn to marry him. Her response, "Yes! Wait, are you serious?!"