Cassidy and Mike met in Biology class at Winneconne High School. She was a Sophomore and he was Junior. They remained good friends throughout the next 13 years. On January 15, 2022, Mike decided to ask Cassidy on a date. They met up at The Mad Apple Bar and Grill to shoot some pool and catch up on life. After four weeks and a few dog play dates later with their furry friends Zeva, Gibbs, and Atlas, Mike officially asked Cassidy to be his girlfriend.

On July 22, 2023, Mike and Cassidy went to visit the Cana Island Lighthouse in Baileys Harbor. When they reached the top of the lighthouse, Mike got down on one knee and asked his best friend to marry him. She said yes, of course.