“Stay a Little Longer” was written in 2011 and originally released on their 2014 self-titled debut EP, but the Brothers Osborne re-recorded the tune for the official single release in 2015.

T.J. Osbourne told Rolling Stone:

That song gives them everything that we are. It starts off, and the verses are really emotional and fragile. You don’t want to be alone, you’re making the phone call [to an on-again, off-again lover], taking the trip to the house, and then you’re tearing T-shirts off, and it’s this electric thing. But then, boom, you’re by yourself again, ‘I’m lying here wishing you could stay a little longer.’