The first woman Sean Penn ever proposed to got cold feet before the couple could walk
down the aisle.
The actor mended his broken heart in his first marriage to pop icon Madonna, but sadly their
romance was full of controversy and endless scandals.
Jealousy, violence, and betrayal are just some of the things headlines reported about
their relationship.
But over the years, Penn's rowdy reputation slowly turned quiet.
And soon, he was rumoured to be engaged to none other than Hollywood's fierce bombshell,
Charlize Theron.
After confirming his lockdown wedding to his new twenty-nine-year-old wife, we couldn't
help but wonder how he scared all the other women away… and is this one here to stay?
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Just last year, when the pandemic hit, it also landed a few blows for couples who hope
to get married in grand celebrations.
But for a reclusive actor like Sean Penn, this couldn't have been more perfect.
When reporters asked for confirmation on whether he truly had entered his third marriage, the
actor flashed his ring to the camera, showing off his wedding band.
Sean and his third wife, Leila George, daughter of DareDevil actor Vincent D'Onofrio tied
the knot quietly during lockdown.
While everyone else was focused on stocking up on the toilet paper, these two were on
a zoom call saying, "I do".
YES, the couple tied the knot over a zoom meeting, with Sean's children and Leila's
brother's in the room with them as their witnesses.
Although sharing such a special day with loved ones or a big crowd is beautiful, the actor
did not seem disappointed at all about his little intimate get-together.
"Let's say there are socially-liberating factors under COVID." he shared on Seth Meyers Late-night
show.
The couple seems to be going strong, with George attending most of her husband's charity
events and supportively getting involved in his non-profit organisation.
However, there's no surprise there because that's how all of Penn's relationships started.
It's always glorious and beautiful in the beginning until it's not.
When Penn fell in love with his Racing With The Moon co-star, Elizabeth McGovern, he couldn't
imagine not spending the rest of his life with her.
And after just a short time together, he proposed and the actress said yes.
But soon, the 23 year old actress realised that she was too young to get married and
had her whole life ahead of her, and instead chose her career over Penn.
Thinking back to whether she would've been Penn's wife, the actress responded,
"Married Sean?"
rolling her eyes.
"I think I was the lucky one to do what I did."
The dazzling actress went on to land several films, including a role in the celebrated
hit show Downton Abbey.
But, while Mcgovern found love and started a family in what is now her twenty-ninth year
of marriage, Penn moved from one relationship to another, with two divorces to his name.
You'll hear the words, "It's not a wedding without a little drama", being tossed around
casually when something unexpected happens at the celebration.
Maybe someone dropped a plate, or some cousins got into a fight, but you never expect to
hear that the groom fired a shotgun at someone.
The day Penn and Madonna said I do, the actor fired a shotgun at a helicopter that night.
"I would have been very excited to see one of those helicopters burn and the bodies inside
melt."
Penn allegedly shared.
Although Penn was infuriated with the press that kept invading his privacy, this became
a reputation of Penn's behaviour in and out of his marriage.
His marriage to Madonna was said to have been full of jealousy.
Although the actor is also in showbiz and should understand how it works, he would lose
his temper anytime men surrounded the singer.
The constant attention Madonna would get eventually got to Penn and left him feeling insecure.
He didn't trust his wife anymore and believed that she was cheating on him.
Although the star denied the allegations, it did not change Penn's mind.
When Madonna's fellow singer and friend was leaving, he didn't make it to the door before
Penn reportedly assaulted him for trying to kiss his wife.
After endless assault charges and landing in prison twice, once for attempted murder,
Madonna tried to flee their marriage.
While Sean was still being held, the actress filed for divorce, but it never stuck.
Following that, the pop star tried to leave the actor again, and well… let's just say,
"I want a divorce" were not the words Penn wanted to hear.
Penn allegedly tied his then-wife to a chair while verbally and physically assaulting her.
For hours he reportedly beat Madonna while she was bound tightly to the seat and even
threatened to chop off her hair.
However, after their divorce, the actress made the record clear claiming that their
separation was not the cause of any abuse she had endured.
She also denied ever being physically assaulted by her ex-husband.
With stories of Penn picking fights in bars and trying to strike a photographer with a
rock, it became very hard for people to not believe the abuse allegations that swarmed
around his marriage.
The constant drama surrounding them even led to the couple's nickname, the "Poisonous Penns".
In contrast to their relationship, the public was shocked to hear that the actor planned
to settle down with a certain Mad Max actress.
Sean and Theron's plus-minus one-year relationship was confirmed in 2013.
Soon there were speculations that Penn was so in love with the actress that he was ready
to propose.
There was even word of them being secretly engaged, which the actress flat out denied.
"No, I did not 'almost get married to Sean,' that's such bullshit."
Theron responded to the rumour, "We never moved in.
I was never going to marry him."
The actress may have denied their union, Penn did not have anything to say on the matter.
However, looking at the star's stack record of marriages, he tends to fall quite quickly
in love.
He proposed to Elizabeth shortly after meeting her, and Madonna said I do after just seven
months with the actor.
So the chances of him having asked for Theron's hand in marriage are quite high.
Theron left many thinking Sean was not ready to have more children, as he was aware that
the actress was ready to adopt her second child the whole time they were together, but
he did not get involved.
"He knew that I was thinking about filing for another adoption but that we weren't filing
together."
Before the almost- marriage to Theron, Sean, who had garnered a rebellious reputation,
had now quieted down.
He met House of Cards actress Robin Wright , and it wasn't long till the two hit it off.
But after fourteen years of marriage and over two decades together, the couple couldn't
stay together for much longer.
"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.
If you've got kids, it's a family, and you try again, and you try again.
We did that for a long time."
the actress shared.
Though the two were constantly on and off, It was clear that Wright had moved on when
she immediately fell in love with someone else.
Although she and Sean had been together for years, there was a whole other world that
she had never experienced, and a then-thirty three-year-old Ben Foster was just what the
actress needed.
Foster was full of adventure and all things new to Wright.
"I'd never, ever been asked out on a date before," she said.
"Never.
I was frickin' married my whole life, and even before that I hadn't been asked out."
And while the actress was on a new adventure, so was Penn.
They both found healing in caring for others, but Penn's love was for the nation of Haiti.
After their devastating split, the actor travelled across the world to help the people of Haiti.
The actor took some time away to help others, and by doing so, he also helped himself heal
in many aspects of his life.
After allowing Oprah to sit down and chat with him in Haiti, the actor seemed to be
done with his rebellious life.
He did not see his divorce as a passport to jump back into his bachelor lifestyle.
Referring to the work in Haiti, the tv host asked how the single life changed him, saying,
"I read that if you weren't doing this, you'd probably be out chasing women or something,
is that true?" which Penn took with a grain of salt, responding, "I am not in the state
of chasing women."
The actor admitted to his past days and acknowledged that it was never a pretty picture when he
had too much time on his hands—eluding to the fact that he would chase women out of
boredom.
Fortunately, after his break-up with Theron and the much-needed healing from his previous
relationship, Penn has finally found someone who makes him happy and who he feels the same
way about too.
But the big question is, will this marriage last?
What if Leila still wants to have children like Charlize?
Will that be a deal-breaker?
Or is he in it for the long haul with this one?
There's only one way to find out, and that's to keep your eyes peeled for more Rumour Juice
news because we'll do our best to keep you updated with the hottest celebrity news.