"You Should Probably Leave" is a song recorded by American singer-songwriter Chris Stapleton, it was released on May 17, 2021, as the second single from his fourth studio album Starting Over. The song was co-written by Ashley Gorley, Chris DuBois and Stapleton, who also produced the track with Dave Cobb.
"You Should Probably Leave" describes a story about an on-again, off-again couple who cannot seem to keep themselves from coming back to one another, even though they know their story will not end well.