Reagan and Matthew first met when Reagan was in eighth grade and Matthew was in tenth. He was the brother of Kait, one of Reagan's best friends. They first bonded over their love for Harry Potter. He asked her out at homecoming the following school year, and she responded with a yes two days later. Four and a half years later, he asked her to marry him while they were dressed as Rapunzel and Flynn Rider from Disney's Tangled on a family trip to Disney World.