Released in May 1989, the power ballad reached #19 on the US Hot 100 and #8 on the US Mainstream Rock chart.

The music video for "Headed for a Heartbreak" was directed by Mark Rezyka and edited by Scott C. Wilson.

Singer Kip Winger was fooling around with his keyboard at the end of a day in the studio, and came up with the riff, which is in D Lydian mode.

He added, "Once I figured out what I had, I rotated the bass notes around the common tones of the right hand on the keyboard stuff, so there was some music theory at play in that song, at the end of it.

"[3] Winger said that for him, the song "exemplifies the band the most because of the way Rod drums and Reb's solo.