In 1986, Richie released Dancing on the Ceiling, his last widely popular album, which produced a run of five US and UK hits, "Say You, Say Me" (U.S. #1), "Dancing on the Ceiling" (U.S. #2), "Love Will Conquer All" (U.S. #9), "Ballerina Girl" (U.S. #7), and "Se La" (U.S. #20). He made his return to recording and performing following the release of his first greatest-hits collection, Back to Front, in 1992.
In 1986, while still married to Harvey, Richie began a relationship with Diane Alexander. He later separated from Harvey, who in 1988 allegedly discovered Richie and Alexander together in a Beverly Hills hotel room by saying she was "room service." In June 1988, Harvey was arrested and charged with corporal injury to a spouse, resisting arrest, trespassing, vandalism, battery, and disturbing the peace after she found Richie at Alexander's Beverly Hills apartment. Richie and Harvey divorced on August 9, 1993, after nearly 18 years of marriage. Richie married Diane Alexander on December 21, 1995. They have a son, Miles Brockman (born May 27, 1994), and a daughter, Sofia Richie (born August 24, 1998). The marriage ended in 2004.