The album debuted at number three on the U.S. Billboard 200 chart, selling approximately 69,000 copies in its first week. Its lead-off single, "Watching Airplanes", reached number 2 on the country charts, while "Learning How to Bend" reached number 13. The album's third single, "She's So California" reached number 24. "Half of My Mistakes" was originally recorded by Radney Foster on his album This World We Live In, and by Jace Everett on his self-titled debut album, both released in 2005. "Like It's a Bad Thing" was later recorded by Danny Gokey on his 2010 debut album, My Best Days.
"Watching Airplanes" was the lead-off single. His twentieth chart single overall, the song reached a peak of number 2 on the Billboard country charts in early 2008. It was written by Jim Beavers and Jonathan Singleton.
"Learning How to Bend" peaked at number 13 in the United States. Written by Gary Allan, James LeBlanc, and Matt Warren. The song debuted at number 51 on the Hot Country Songs chart dated April 5, 2008.
"She's So California" was the third and final single, written by Allan along with Jon Randall and Jaime Hanna of Hanna-McEuen. It peaked at number 24.
The song is an up-tempo in which the narrator uses various California-themed imagery to describe his lover, whom he says is "so California." Blake Boldt of CountryUniverse.net gave it a B- rating, saying it was "little more than album filler", calling the production both "modest" and "a bit sterile", but saying that Allan's "gravelly vocal" was of note.