Head over Heels was released after Abdul's four-year hiatus while battling bulimia. The album was considered Abdul's comeback album, intended to bring her back into the limelight, but it would be the last album Abdul would release before her second hiatus from music.
Head over Heels showcased a new direction and style of music for Abdul, including a more R&B and "sensual" feeling to her songs. The first single released from the album, "My Love Is for Real", was a taster of her new-found sound, however reviews were mixed.
Head over Heels received mixed reviews. Many reviewers claimed it diverted from Abdul's pop music roots, however some reviews said the album was Abdul's most creative and exciting work to date. The iTunes review of the album was mixed, saying that Head over Heels included songs which "lack strong hooks" yet praised the album for being "more mature and seductive than previous efforts". The review mainly concentrated on the length of the album and how it "spends too much time on lesser songs".
Head over Heels did not do as well as Abdul's previous albums in terms of chart performance and sales. It was Abdul's weakest selling album to date, only going gold; it was also Abdul's lowest peaking album on the Billboard 200 to date, peaking at #18, and it quickly fell off the charts soon after. The album managed to become her lowest selling studio album (in terms of international sales) in her career. After the relative failure of the album, Abdul left the music scene and ventured into acting and returned to choreographing.
Three singles were released from Head over Heels. The first single, "My Love is for Real" peaked at #28 on the Billboard Hot 100. It was Abdul's first single to not reach the Top 20 and was considered a flop. However, the song went to #1 on the U.S. dance charts (her only song to do so). The following single, "Crazy Cool" peaked at #58 and was considered another flop, probably due to bad publicity about the song and its video. The last single from the album "Ain't Never Gonna Give You Up" tanked and failed to chart. However, it did peak at #12 on Bubbling Under Hot 100. A fourth single, "If I Were Your Girl" was due to be released, but was cancelled after disappointing album sales and the failure of "Ain't Never Gonna Give You Up".