"Looks Like Rain" has been a fan favorite since long before it was ever released. A love song, a goodbye note, a clean start. Peay's songwriting is front and center in this acoustic version. Fans had been asking for the song to be released for purchase for a long time. When "Looks Like Rain" couldn't seem to find its place on an album, Peay decided to release it as a digital single.

Packaged with 2 B-Side tracks, including Peay's commentary on the decline of the middle class in "Paper America" and a cover of Leonard Cohen's "Hallelujah." All three songs on "Looks Like Rain" place songwriting above all else, and were recorded with only acoustic guitars and vocals.