Written by Go-Go's Kathy Valentine and Charlotte Caffey, this song is about a girl who has gotten caught up with the day-to-day challenges in life and now realizes that she should follow her heart and let her emotions lead her. In a Songfacts interview with Valentine, she talked about the meaning of the lyric. "This is one where I had a lot of phrases I'd written down, and they started connecting. Things like 'One hand is reaching out, and one's just hanging on,' and 'Seems like my weaknesses just keep going strong' were really about self reflecting and a dawning awareness that the band and certain areas of life were getting kind of out of control."
In our interview with Charlotte Caffey, she said of writing this song: "I played piano and I had never utilized it, really, in the Go-Go's and I thought, Well, maybe it would be a cool idea to try something with the piano, just get a little different tonality happening other than just guitars. I sat down and came up with the hooky part in the beginning, the 8th note-y part. I wrote it, and I asked Kathy if she wanted to finish it with me. I started on something and worked on it for a while, and then we worked on it together, and then we finished it. I had maybe ¾ of the song written, and then Kathy came in and helped me finish it."
The Go-Go's had to cancel their 2010 tour when Jane Wiedlin fell off a cliff while hiking and injured her knees. This event made #9 on Entertainment Weekly's "Hit List" in their June 25 issue, where they wrote: "Probably wasn't the best idea to rehearse 'Head Over Heels' on the trails."
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