Celebrities Sean Penn's Loves & Hookups  

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Who is Sean Penn dating? Who Sean Penn dated; list of Sean Penn loves, ex girlfriends; marriages and breakup rumors. The loves, exes and relationships of Sean Penn, listed by most recent. Now that Sean Penn's no longer has a wife, it'll be interesting to see what Hollywood starlets he links up with. Will he fall for the roster of famous babes that end up in celebrity "tapes?" Not to say anything about Sean Penn, but his celeb tape would probably be something you watch out of curiosity as opposed to it being hot. Who knows if he'll end up on the list of celebrities with such tapes anytime soon...

Which of Sean Penn's exes is the hottest?

1

Leila George D'Onofrio

Leila George D'Onofrio is listed (or ranked) 1 on the list Sean Penn's Loves & Hookups
Photo: Brad Barket/Getty Images

Sean Penn began dating actress Leila George, daughter of actor Vincent D'Onofrio, in late 2016. 

Leila George D'Onofrio is the daughter of Vincent D'Onofrio and Greta Scacchi. ...more on Wikipedia

Age: 26

Birthplace: Sydney, Australia

Charlize Theron is listed (or ranked) 2 on the list Sean Penn's Loves & Hookups
Photo:  Fuzheado/Wikimedia Commons

Sean Penn started dating Charlize Theron in 2013, but the pair split just over a year later.

Charlize Theron (born 7 August 1975) is a South African-American actress and film producer. She is the recipient of several accolades, including an Academy Award, a Golden Globe Award, and the Silver Bear for Best Actress. Theron came to international prominence in the 1990s by playing the leading lady in the Hollywood films The Devil's Advocate (1997), Mighty Joe Young (1998), The Cider House Rules (1999). In 2003, she received critical acclaim for her portrayal of Aileen Wuornos in Monster, for which she won the Academy Award for Best Actress, becoming the first South African to win an Oscar in a major acting category. Theron has since starred in several top-grossing action films, ...more on Wikipedia

Age: 42

Birthplace: Benoni, Gauteng, South Africa

Also Ranked

#16 on The Most Beautiful Women of All Time

#26 on The Best American Actresses Working Today

#92 on The Greatest Actors & Actresses in Entertainment History

#10 on The Most Beautiful Women In Hollywood

see more on Charlize Theron
Calu Rivero is listed (or ranked) 3 on the list Sean Penn's Loves & Hookups
Photo:  Gobierno/Wikimedia Commons

Rumor has it that Sean Penn linked up with Calu Rivero in 2012.

see more on Calu Rivero
4

Shannon Costello

Shannon Costello is listed (or ranked) 4 on the list Sean Penn's Loves & Hookups
Photo:  Sachyn Mital/Wikimedia Commons
Sean Penn dated Shannon Costello from 2011 - 2013.

Shannon Costello is a film producer. ...more on Wikipedia