Winnie and Greg first met in the second grade at Dewitt Elementary School. Both attended Bolich Middle School and Cuyahoga Falls High School where they graduated in 2006. In December 2014, nearly a decade after their high school graduation, a small group of Winnie and Greg's graduating class met at Darby's in Cuyahoga Falls. The two, hugged, said hello and began a conversation that would last for the remainder of the night. Just a few weeks later, Winnie and Greg went on their first date. They talked and laughed for hours and have been inseparable ever since. On February 25, 2017, Greg proposed to Winnie near a secluded waterfall in the Hocking Hills forest.