“When Will We Know” tells the story of two lovers, out on the road, testing the limits of their love. How deep does love go? How long does love last? These are questions that go through the singer’s mind as he sits by the riverside with his love. Is her presence comfort enough to last him a lifetime? When will we know? It seems like a question at first but by the end of the song, it turns into a realization that we won’t know and that’s ok. The Texas fiddle hook and the traditional country pedal steel guitar bring home the message of the song.