Cyndi has noted that her relationship with Dave was largely ruined by their differing views on where her career should go. "Once the business snuck into our relationship, it ruined it", she said in 2002`s Behind the Music. He wanted her to record pop hits and stay with her current image. Cyndi was not happy with this, being more concerned with artistic efforts and making a statement. In 1988, while working on Lauper`s album, A Night To Remember (1989), they met in his New York office and agreed to end it. (it is implied by his comments that she was the one who officially decided they should no longer see each other).
The split was hard on Lauper; she was close to ending her career, and the album flopped with only one #1 hit, I Drove All Night. She took time off and went onto making movies (Off and Running) in 1991. She and co-star David Thornton fell in love and married later that year.