Songfacts®:

• It was hoped that this single about a troubled breakup would become a single ladies' anthem. Consequently to promote its release, Trina's record label ran ads on Internet dating sites and sponsored blind-date contests on radio stations. However it performed disappointingly only reaching #125 in the Billboard Hot 100.
• Rap-Up magazine asked Trina if any of the song's on the album would surprise the listener. She replied: "I think definitely the first single ["Single Again"] with me singing on the hook. That was so different. I was in the studio like, 'Okay, I'm not a singer so what am I doing?' But I went from humming along in my head to making it a reality out loud. And when I sang the hook, everybody was like, 'Oh that's crazy!' It was a lot of fun for me.'"
• The official remix featured Lil Wayne, who dated Trina in 2005-06. He told Rolling Stone that he was surprised to be asked to help out on this track. Weezy explained to Rolling Stone: "She asked to jump on 'Single Again' when clearly [our breakup] was the subject of the song. That was kinda weird, but I did it."