49. Pamela Anderson and Jon Peters
American actress and model Pamela Anderson, 52, and film producer Jon Peters, 74, date back more than three decades. The two have met in the eighties in a Playboy Mansion party, through their Hollywood careers, and dated briefly over 30 years ago. After their first separation, the Bay Watch star had a turmoil of relationships: she was married to singer Tommy Lee in the late nineties, and had two sons with him; after their separation, the actress was married shortly to rapper Kid Rock, and in the mid-2000s, she was married to producer Rick Solomon, while the Batman producer was also married two times, to actress Lesley Ann Warren and later producer producer Christine Forsyth-Peters. In 2019, after more than 30 years apart, the couples reunited, but this reunion wasn’t meant to be.
In January, 2020 Anderson and Peters tied the knot in a secret Malibu ceremony, but as it turns out, they weren’t yet ready to make this commitment. Only 12 days after exchanging vows, the actress revealed they had decided to break up, taking time apart to rethink this decision and what they want in life. Rumor has it Anderson was the one who proposed to Peters, and the marriage was meant as a way to pay off her debts.