In September 2018, Whitney and Matt's good friends from college got married in Half Moon Bay, CA. Whitney was a bridesmaid and Matt served as the emcee of the wedding. To make sure he was pronouncing the bridal party names correctly, Matt spoke with each member prior to the reception to confirm how they’d like to be introduced. According to Matt, the moment he locked eyes with Whitney and she smiled at him, he was a goner. But it wasn’t really until Matt took the stage with the band to sing Montell Jordan’s “This is How We Do It,” that Whitney felt the same. They danced all night, eventually making a wager on what the last song of the night would be. Whitney picked “Sweet Caroline,” which often closed the night at their college bar The Tombs (where their two college friends had met). Matt, an experienced wedding guest, went with “Don’t Stop Believin',” which would turn out to be the correct guess. However, no stakes for this bet were ever established.

Because Matt had won the bet the night he and Whitney met, every time he heard a Journey song, he reminded Whitney of his win. It didn’t even have to be “Don’t Stop Believin'", it could be “Open Arms,” “Faithfully,” “Separate Ways,” “Lights”...you get the idea. It became a running joke in their relationship that Matt was overdue to collect his winnings. Matt knew he wanted to incorporate “Don’t Stop Believing” into the proposal, but went back and forth deciding whether or not to propose in front of friends. So he turned to the 80s music gods. While preparing for friends to come over that afternoon, Matt put on an 80s music playlist to decide his fate. If a Journey song came on – which, of course, it did – he would propose with just the two of them. As this was during the pandemic, the friend group was planning a rooftop gathering. Under the guise of helping to move patio furniture around prior to their friends arriving, Matt lured Whitney to the rooftop of their apartment with a speaker in his pocket. He queued up “Don’t Stop Believing” and when it came on, Matt made a comment about the bet and Whitney began her usual protest that he had run out of time to cash in. This time, Matt got down on one knee and asked Whitney to marry him.