By 1993, Bolton was spotted with another of his video girls: Paula Barbieri, who starred in his music video for "Completely" (via Alchetron). But a truly Earth-shaking romance for the singer came in 1996 with actress Ashley Judd, who "credits him with helping her out of a deep depression" (via Snakkle). Judd also starred in Bolton's music video for "The Best of Love" in 1997, which was the end of their relationship.
Soon enough, the crooner might have struck a fling with "Baywatch" actress Pamela Anderson, with the two possibly meeting in 2001 at a party in the Bahamas (via Famous Fix). While their time together only lasted about a month, Bolton quickly moved on to American dancer and actress Deborah Yates, dating from 2001 to 2002. There's no doubt the "Go the Distance" singer is quick!
Bolton reportedly dated Malta-born actress Valentina Agius in 2003, who later married Olympic gold medalist Mitch Gaylord (via Who's Dated Who). The soul singer had a brief fling with "Entertainment Tonight" host Nancy O'Dell in 2003 (via Famous Fix), possibly meeting in an interview, but Bolton's most publicized romance didn't come until 2005.
