You Should Probably Leave

This bluesy, rootsy song finds Chris Stapleton talking to his former partner in a messy relationship. They have met up for a reunion and Stapleton realizes the attraction is still there. He tells the girl she should step away before they give in to temptation and do something they will later regret. 'Cause I know you and you know me And we both know where this is gonna lead You want me to say that I want you to stay So you should probably leave

There is a twist in the third verse when Stapleton reveals they spent the night together. It is now the next morning, and the singer hopes when his ex-wakes up, she doesn't think it was a mistake and tell him he should leave.

Chris Stapleton wrote the song with two fellow Nashville songwriters: Chris DuBois and Ashley Gorley. It is the oldest track on Starting Over with various performances of it from the mid-2010s uploaded to YouTube, including one from Musicians Corner in Nashville in October 2014.