A deep dive into Sean Penn's star-studded romantic past

From Madonna to Charlize, and all the talented women in between

Stars Insider

08/13/19 | StarsInsider

CELEBRITY Sean Penn

Sean Penn's reputation in Hollywood is a mixture of high regard for his profound work in films like 'Milk' and 'Mystic River,' along with some reticence with his eccentrically grumpy persona off-screen. He's gone from strength to strength in acting, and gone from controversy to controversy in headlines, but there has been one constant among it all...

His affinity for talented women. Penn's private life has been more of a hot topic than many of his films in recent years, and there's good reason for it, what with his romantic journey among the likes of Susan Sarandon and Charlize Theron leading to dating someone one year younger than his own daughter. 

The actor, who turns 59 this year, has cultivated a wild, experimental nature over the years, and yet has proposed to four different women. Click through this gallery to see all the women Penn has romanced, or has been rumored to romance, over the years. 

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