Lose Again

"Lose Again" was written by Bonoff; one reviewer dates it to 1975. Ronstadt recorded it in March 1976 at The Sound Factory with Peter Asher producing, and it opens side one of Hasten Down the Wind at 3:34. It was issued as the album's third single in May 1977 on Asylum, backed with "Lo Siento Mi Vida", and reached number 76 on the Billboard Hot 100 for five weeks, her lowest Hot 100 single to that point, with number 43 on Adult Contemporary. Cashbox called it one of the best from the album. Bonoff's own version is track three of Karla Bonoff (1977), 3:42, produced by Kenny Edwards, and it also appears on the compilations Premium Best, The Best of Karla Bonoff (1999) and All My Life.

How Ronstadt came to it is told three ways. Wikipedia says Edwards, who played in Ronstadt's band and was dating Bonoff, played her a demo. Bonoff recalled in 2018 playing Ronstadt a tape herself, with Ronstadt answering that it was real good and asking what else she had. In a 2000 interview in Performing Songwriter she said she heard through Edwards that Ronstadt had learned it, that the band played it at sound check and then in the show, and that she heard it at the Universal Amphitheater and thought it was so cool. These accounts are not reconciled.

One review summary describes the song as about the tribulation of keeping a long relationship going after the bloom is gone, but we could not confirm it, and we found no statement from Bonoff about its meaning. David J. Cantor of SoundStage! found Alison Krauss's version peppy and direct and Bonoff's own slow and lumbering, and called the lyrics vague with mixed metaphors; Wikipedia names Krauss as a cover, but we could not verify an album or year. Bonoff played it at The Kent Stage in Ohio on April 6, 2018 and at AMP by Strathmore in Maryland on April 1, 2022. We did not get a setlist.fm play count, and the version of our upload is not known.