Sean Penn is an American actor and filmmaker with an impressive dating history. He has been associated with a number of high-profile women over the years, including pop star Madonna, actress Charlize Theron, and model Petra Nemcova.
Penn began his career in the mid-1970s, appearing in films like Fast Times at Ridgemont High and Taps. During this time, he began dating singer-songwriter Madonna, who was in the early stages of her career. The couple had a tumultuous relationship and eventually split in 1989.
The actor then moved on to actress Robin Wright, with whom he had two children. The couple married in 1996 but divorced 15 years later in 2010.
In 2013, Penn began dating South African actress Charlize Theron, who he met while filming The Last Face. The couple was engaged in 2014 but split by the end of that year.
In 2015, Penn began dating model Petra Nemcova. The couple split in 2016 but remain good friends. The actor has since been linked to a few high-profile women, including Emma Stone and Scarlett Johansson, though none of the relationships have been confirmed.
Overall, Sean Penn has had a successful and exciting dating history over the course of his career. He has been linked to a number of high-profile women and his relationships have kept the media abuzz for years.