In the same year, Anderson started seeing entertaining American singer, rapper, and record producer Robert James Ritchie, better known as Kid Rock. They met the previous year at the VH1 Aretha Franklin Tribute Show. Kid Rock became the third guy to propose to Anderson.
In the year 2002, he popped the question; he thought it was appropriate to call up her ex-husband Tommy Lee to tell him the news before he the tabloid does; Lee was furious. They called off their engagement within the year.
Pamela and Marcus Schenkenberg
Soon after, Anderson met Calvin Klein model Marcus Schenkenberg in Monaco. His modeling and acting career aside, Schenkenberg also made magazine covers from his 10-month relationship with the actress. This attractive couple had kept their privacy and rarely made appearances in public, apart from the Iceberg ad they did together.
They broke up in 2001 because of their busy schedules, he wanted to focus on his career, and she wanted to focus on her kids.
Shortly after breaking up with Schenkenberg, Anderson was invited to Michael Jordan’s Celebrity Golf Invitational Opening Party in Paradise Island, Bahamas. There she met and challenged American songwriter and ballad singer to a tequila drinking contest.
She went on to win the contest against Bolton. He helped her get over the breakup with Schenkenberg. That being said, it was a short-lived romance.
Anderson had a small fling with American lead singer and lyricist of Limp Bizkit quite soon after splitting with Kid Rock in 2003. William Frederick Durst had a successful career with the nu-metal band, Limp Bizkit.
These two were seen out for a few dates but ended up going their own way. The rocker has since moved on to direct independent films.
Taking a break from the Rock & Roll scene, Anderson got close with her long-term friend and fellow American actor Stephen Dorff (Stephen Hartley Dorff Jr.) for five months. Stephen, born on July 29th in 1973, is known for his role as Roland West in HBO’s "True Detective."
Their relationship didn’t end in flames; they just naturally parted – and reconciled in 2008 for one crazy night in Miami.