Diana and Matt were introduced by their mutual friend, Stephanie. Diana went to high school with Stephanie and Matt worked with her at the Jewelry Exchange. Stephanie had noticed that both Diana and Matt were constantly quoting The Simpsons, so she decided to introduce the two. Diana and Matt went on a double date with Stephanie at the Cheesecake Factory where they shared a white chocolate raspberry truffle cheesecake slice.

On Friday, March 31, 2017, Diana and Matt were having dinner at home. The night before, Matt had picked up a slice of white chocolate raspberry truffle cheesecake from The Cheesecake Factory, the restaurant that Matt and Diana had their first date. Diana asked if Matt wanted to split it, he said yes, but he would get it, despite the fact that Diana was closer to the fridge. When Matt brought the slice, Diana's engagement ring was sitting is in the whipped cream. Matt asked Diana, on bended knee, to marry him and she said yes. They celebrated by splitting a slice the flavor of cheesecake they had on their very first date.