Sean Penn has had a number of high-profile relationships. Here's a deeper look at his love life.

Charlize is no Casper! In a candid new interview with WSJ magazine, Charlize Theron opened up for the first time about her failed romance with actor Sean Penn. When the pair split over the summer, ...

In a candid new interview with WSJ magazine, Charlize Theron opened up for the first time about her failed romance with actor Sean Penn. When the pair split over the summer, there were rumors going ...

Boyfriend on duty! Sean Penn joined girlfriend Charlize Theron on a trip to the grocery store with her 2-year-old son, Jackson, in L.A. on Wednesday, Jan. 22. The 53-year-old actor helped keep Jackson ...

“There is a need to sensationalize things. When you leave a relationship there has to be some fucking crazy story or some crazy drama. And the fucking ghosting ...

Charlize Theron has called off her engagement to Sean Penn after a year and a half relationship and here's why A close source to the 'Mad Max: Fury Road' star tells HollywoodLife on June 17, ''To be ...

Charlize Theron confirmed that she is on dating app Raya while sharing rare comments about her dating life. The Old Guard 2 actress opened up about why she's struggled to find love on the popular app.

Are Angelina Jolie and Sean Penn dating? One of this week's tabloids claims the actress is hooking up with the actor to get revenge on Brad Pitt for supposedly moving on with Charlize Theron. The ...