From Madonna to Leila - a look at Sean Penn's marriages

Divorce after 1 year of marriage
The pandemic brought them together
Sean and Leila had a COVID wedding
Sean and Leila worked together during the pandemic
Was the age difference the issue?
Madonna was Sean Penn's first wife
They met on the 'Material Girl' set
Love at first sight
After one year the marriage was on the rocks...
Madonna and Penn are still friends
Sean started a family with Robin Wright
The couple had several issues
A devastating divorce in 2009
Not an amicable parting
Will Sean marry again one day?
Divorce after 1 year of marriage

According to TMZ, on October 15th, Senn Penn's third wife, Leila George, filed for divorce. The Australian-American actress and Penn were married for just one year, having tied the knot in July 2020, following four years of dating.

The pandemic brought them together

People Magazine reported that Leila and Sean had been having an "on and off" romance for several years. However, it seems that the extra time spent together in isolation brought the pair together and prompted their decision to get married.

Sean and Leila had a COVID wedding

Sean Penn confirmed that he had indeed had a "COVID wedding" in August of 2020 during an interview on 'Late Night with Seth Meyers.'
"We did a COVID wedding. By that I mean it was a county commissioner on Zoom, we were at the house, my two children and her brother, and we did it that way," Penn said during the interview.

"Leila pushes me to be better"

Later in August 2020, Penn gave an interview on the podcast the 'Armchair Expert with Dax Shepard.' When asked about his new wife, Sean said, "Leila certainly pushes stuff to the surface that has to be understood for me to be better at stuff — a better person, better communicator."

Sean and Leila worked together during the pandemic

It seems that Leila George encouraged Penn not just to be a better communicator but also to help out in the community. According to a source that spoke with People magazine, Sean and Leila not only isolated together during the height of the pandemic but also worked side by side to set up COVID-19 test sites in Los Angeles.

Was the age difference the issue?

Leila George is just twenty-nine years old and has a 31 year age difference with Sean Penn, who is currently 61. Perhaps a generational clash was the cause of the split? Leila is the daughter of Australian actor Greta Scacchi and American actor, Vincent D'Onofrio. Leila's father is just one year older than Penn....

Madonna was Sean Penn's first wife

It certainly appears that Sean Penn has terrible luck when it comes to making marriages last. His first marriage was in 1985 to the QUEEN of Pop, that's right, Madonna.

They met on the 'Material Girl' set

According to Showbiz Cheat Sheet, the pair met on the set while shooting for Madonna's 'Material Girl' music video. Penn had stopped by to visit Meegan Lee Ochs, his former assistant who was working there.

Love at first sight

The story goes, Madonna and Sean locked eyes, and it was love at first sight. After dating for just six months, the couple got married on Madonna's 27th birthday.

After one year the marriage was on the rocks...

Unfortunately, after just one year of marriage, things were not going very smoothly. According to various media outlets, Sean had difficulty dealing with Madonna's extreme fame and became very jealous and insecure. According to People Magazine, Sean was so jealous he believed that Madonna had cheated on him with singer Nick Kamen.

Madonna and Penn are still friends

These issues led to a very public and dramatic divorce by 1989. According to Marie Claire, sources accused Penn of domestic abuse. However, Madonna called them false claims and defended Penn. Surprisingly, despite all the drama, Madonna and Sean are still close friends.

Sean started a family with Robin Wright

Following his disastrous relationship with Madonna, Penn had better luck with his second wife, Robin Wright. The couple were married from 1996 to 2010 and had two children together.

The couple had several issues

Even though they had a relatively "long" marriage, it was not without its tensions. Media outlet The Things reported that Robin was unhappy that Sean expected her to hit "pause" on her acting career to care for their children while his career continued full speed ahead.

A devastating divorce in 2009

In August of 2009, the couple filed for divorce due to irreconcilable differences. Robin told People Magazine that the divorce was "devastating."

"....trying to keep the family together..."

Robin Wright also spoke about the divorce with Penn to The Telegraph in 2014: "Divorce in and of itself, and with children, is devastating. Worse than that. One of the reasons why we got back together and broke up so much was trying to keep the family together."

Not an amicable parting

Unlike with his divorce with Madonna, Sean Penn and Robin Wright did not remain friends. Penn told People that he does not have frequent communication with Robin and that they maintain "separate relationships" with their children.

Will Sean marry again one day?

Now, with his divorce from Leila George, Penn finds himself heartbroken yet again. Will the actor give up on the institution of marriage, or will he try again and get luckier on his fourth marriage? Only time will tell!

Más para ti