Who Is Sean Penn Dating? Here’s A List Of His Ex-Boyfriends & Girlfriends

Who Is Sean Penn Dating? Here’s A List Of His Ex-Boyfriends & Girlfriends

This Academy Award-winning actor got people asking and searching for Sean Penn dating history when the news went around that he is now dating the youngest daughter of fellow actor Vincent D’Onofrio. The two were spotted several times spending time together and going on dinner dates. For good reasons, the “book” of Sean Penn’s dating history has seen no addition since then which is quite unlike what is typical among celebrities.

Let’s find out who Sean Penn is dating in addition to knowing his ex-girlfriends (and boyfriends) being that he has had a long list of women he had an affair with ever since he became a public figure, this list will also mention women he was rumored to have dated or had a fling with.

Who Is Sean Penn Dating? Here’s A List Of His Ex-Boyfriends & Girlfriends

Sean Penn is not gay and as such is not known to have dated any man.

Stacey Nelkin

Who Is Sean Penn Dating? Here’s A List Of His Ex-Boyfriends & Girlfriends
Image source

Sean Penn’s dating story with Stacey Nelkin started and remained as a rumor. At best, the two had a fling together with nothing more between them. Stacey is an actress famous for works like Manhattan and Halloween III.

Peggy Trentini

Sean’s affair with Peggy Trentini came to put an end to the rumors about his fling with Stacey. The two were reportedly romantically involved with each other at the time before deciding to end their relationship. The reason for this is not yet known to us.

Brigitte Nielsen

We got to know of her romance with Sean Penn after she wrote about it in her autobiography. Brigitte is a Danish actress known for works like Red Sonja, Cobra, Rocky IV, Beverly Hills Cop II, and many others.

Elizabeth McGovern

Between 1983 and 1984, Sean Penn dated Elizabeth McGovern. On-screen, they were both in the 1984 film Racing with the Moon. While it might not be wrong to assume that working on the film project together helped bond their emotions for each other, it will also not be wrong to assume that whatever was between them was totally ephemeral as Sean Penn dated two more women in that same year.

Barbara Hershey

Image source

After Elizabeth came Barbara who took a spot on the list of women Sean has dated. Their 1984 relationship like many others before it also didn’t last long as Sean moved on to another woman.

Susan Sarandon

Susan was the last woman to date Sean in 1984. Their relationship was never expected to last long as Sean has come to be associated with not lasting long in any relationship he goes into.


Madonna‘s relationship with Sean Penn was not just like the others, the love between them was so real that it led them to get married. The two hooked up in February 1985 and married on 16th August 1985. Sadly by 14th September 1989, they were no longer husband and wife.

Jewel Kilcher

After his divorce from Madonna, he began dating Jewel Kilcher in a relationship that lasted just for a year before moving on to his next heartthrob being that he gets them as quickly as he wants.

Sean Penn And Robin Wright Penn

Who Is Sean Penn Dating? Here’s A List Of His Ex-Boyfriends & Girlfriends
Image source

With Robin, everything seemed right in Penn’s life. They first got together in August 1990, dated for 6 years before marrying on 27th April 1996. Their union went on to last for 12 years before it hit the rocks and ultimately succumbed to a sad divorce in July 2010. In the good times when they were together, they had 2 children – Dylan Frances and Hopper Jack – who are now adults.

Emily Lloyd

Following his divorce, Sean Penn became the subject of celebrity gossip when he was reported to have spent a night with Emily Llyod. Beyond this, nothing more was said of the two and it was best to leave it at that.

Elle Macpherson

After his affair with Emily, Elle Macpherson entered the picture as the two began seeing each other in 1996. In the beginning, it looked as if they would take the relationship further but nothing came out of it.

Petra Nemcova

Sean had a brief affair with Petra beginning in January 2008 before they separated from each other. Going by the numerous relationships he had in the past, most people were certain that his relationship with Petra Nemcova wouldn’t last and yes, it didn’t.

Jessica White

Between August 2009 to September 2010, Sean dated American model, Jessica White who is famous for Sports Illustrated`s Swimsuit Issue of 2003 – 2005, 2007, and 2008. Their relationship ended with each moving on with the new partners in their lives.

Valeria Golino

After White, he gave us reasons to conclude that an addition has been made to the dynamic Sean Penn dating list when he was spotted severally going on dates with Valeria. It continued with a few more dates before they went their separate ways or rather people stopped seeing them together and concluded they were now apart.

Sean Penn And Scarlett Johansson

Image source

Scarlett Johansson and Sean briefly dated as it became obvious at this time that Sean Penn knew his way around women. Between February to June 2011, the pair was inseparable till what happened in all of Sean’s relationships happened again. We still don’t know what it is that causes his frequent breakups.

Garcelle Beauvais

Garcelle Beauvais and Sean Penn dating was just a rumor like a few others. However, for every rumor that there is, an element of truth may be found in it. The two were spotted at a dinner date first in 2011 and every other thing that was suspected to have happened in their relationship was within that same year.

Shannon Costello

Sean was all over Shannon Costello between July 2011 through 2013, making appearances with her in several public places as he had frequently done with his other dates but yet again this wouldn’t be his last.

Calu Rivero

By April 2012, Calu Rivero was rumored to have hooked up with Sean Penn and had a thing going with her till his next beau came calling. Calu, like most of his other dates, is an accomplished actress with several works to her credit.

Charlize Theron

Sean met Charlize Theron in December 2013 and got engaged with her for 7 months which saw to their 11 months of dating. It seemed they would go the path of marriage but by June 2015, it was all over.

Minka Kelly

A few records have it that Sean and Mina Kelly began seeing each other in 2015, but it has not been certified whether this was a romantic relationship between the two or they were just acquainted with each other being that they are both actors.

Sean Penn And Leila George

Who Is Sean Penn Dating? Here’s A List Of His Ex-Boyfriends & Girlfriends
Image source

Beginning in late 2016, Sean Penn’s dating adventure rested with the daughter of actor Vincent D’Onofrio Leila George who is also an actress. The two made headlines when they were spotted together at a beach and shared a deep kiss with each other. An age gap of more than two decades exists between the two in addition to Sean Penn being a year older than Leila’s father.