Eldredge told The Boot
that the "what if?" story of parting ways is based on a real person, but he didn't disclose if his ex is actually named Gabrielle.
Said the singer: "It's kind of a breakup song, but with the bittersweet, kind of happy, wishing the other person well within their life, wherever they are, but you still kind of look back and wonder, you know, at a certain point in your life, or often, what that person's up to and where they are now, and what it could have been and what if, you know? It's one of those kinds of songs, and the nostalgia of that."