The Women Whose Hearts Were Broken By Sean Penn

Sean Penn and Charlize Theron at the Oscars

When songstress Jewel, known for her soft ballads and lovely voice released her memoir, the world was shocked at some of her revelations, to say the least. Perhaps the most shocking revelation in her book was that when she first began her career as a singer, she fell in love and secretly dated actor Sean Penn. Her sweet, kind demeanor and her very subtle personality do not make her seem much like the type that would fall for a man like Penn, especially after what it was that he allegedly did to Madonna during their marriage in the 80s. However, she goes on and on about their relationship, which lasted much of 1995.

During this time, she was given her first big television break and Sean Penn was recently separated from Robin Wright, whom he would later marry and then divorce. He made it his mission to track her down, calling her at home to eventually end up hung up on during several calls. Jewel’s father did not believe that the man on the phone when he picked it up that 1995 day was the real Sean Penn, but it turned out that was precisely whom he was speaking with.

Sean Penn wanted Jewel to write a song for a movie he was working on, and he asked to meet her anytime, anywhere at her choosing. The two met at a salon in California, and from there they became secretly inseparable. They went to premiers together, they traveled together and they spent much of their time together. Jewel writes that she spent her time not giving him the time of day, not looking to be just another conquest for the famous actor. She said that part of her stipulation was that he had to be completely sober during their time together, and she goes on to say that the two fell madly in love during their courtship. Sean Penn pursued her heavily and then left her on her own.

Jewel describes Sean Penn as completely romantic, persistent and very flirtatious. She says it was difficult not to fall for a man like him – after all, he is the Sean Penn. However, their lives did not work out quite like they thought they might, and he eventually went back to Robin Wright, married her and the couple had two children together. It turns out that she was merely another cog on his wheel of women, and just one of the many women that Sean Penn went on to hurt throughout his long career in Hollywood.

He’s the man accused of beating his first wife, famous singer Madonna, in the head with a bat and then tying her to a chair for more than 14 hours while he tortured her during the 80s. She had him arrested and then she refused to press charges against him, but she did divorce him. He’s the man who recently filed a lawsuit after another person called him an abuser, and his reputation is not very good. We don’t know if it’s true or not; all we know is that many people seem to believe it is true.

That leads us to this; what is it about Sean Penn that seems to make the ladies fall so madly in love with him all the time? He’s not your classically handsome man, like George Clooney or even Brad Pitt. He’s certainly a wonderful actor, but what is it about Sean Penn’s personality that makes him so irresistible to women all over the world? What is it about him that causes so many of Hollywood’s leading ladies, the most beautiful leading ladies, to fall for this man?

He’s broken a string of hearts around Hollywood, many of them very famous and very beautiful. Throughout the course of his long career, he’s been with many women and rumored to be with more. He was married to Madonna in the 80s and Robin Write for 14 years from the mid-90s to 2010. He was rumored to have dated and left women such as Brigitte Nielson and Barbara Hershey before his marriage to Madonna. He even dated Elizabeth McGovern before he married Madonna. There is a rumor he dated supermodel Petra Nemcova for a while during the time in which he was still married to Robin Wright, and he was accused of cheating on her on more than one occasion throughout the course of their marriage.

In the time that he was recently divorced from Robin Wright, he dated Scarlett Johannson. She was 26 at the time, and he was 50. Their relationship lasted all of five months and friends of the actor and the actress say that he was not interested in being tied down to the young actress, so he left her behind. She was allegedly desperate to be in a relationship with him to the point that she would made a fool of herself in front of other Hollywood heavyweights and he would sneak into and out of events so that he did not have to see the young actress. If that’s not heartbreak, I don’t know what is.

His next high-profile relationship came in the form of Academy Award-winning actress Charlize Theron. While it might not be true that he broke her heart, he certainly did something that caused her to give up on their two year relationship and their year-long engagement. The couple began dating in 2013 and became engaged in 2014 and she merely stopped answering his calls and texts with no reason, answer or story to give in 2014. Sean Penn appears not to have cared all that much, though, because he’s moved on. His latest conquest seems to be model Minka Kelly, as the two have been spotted out and about in recent months.

Sean Penn might not be the world’s most handsome man, but there must be something really amazing about his personality because he’s got a long list of broken hearts in his past, and all of them from beautiful, talented and very amazing women who have careers and lives of their own.

Photo by Getty Images

Basketball Wives Big Brother Dancing With the Stars Keeping Up with the Kardashians Love and Hip Hop Hollywood Married to Medicine Million Dollar Listing Mob Wives Real Housewives Shahs of Sunset The Voice Top Chef Vanderpump Rules WAGS
Getting to Know the Cast of Going off the Menu
Getting to Know the Cast of Don’t Be Tardy
No Preview
Getting To Know the Cast of Below Deck
Celebrity Gossip Entertainment
Sarah Harding
20 Notable Celebrities Who Died in 2021
Isla Fisher
20 of Our Favorite Aquarius Celebrities
Amy Schumer
20 of Our Favorite Gemini Celebrities
Charles Barkley Net Worth
Don King Net Worth
Five Under the Radar Celebrities With Huge Net Worths
Brad Pitt Net Worth
Daisy Ridley Confirms Talks about Starring in Lara Croft Reboot
No Preview
10 Great Actors Who Appeared in Cheesy 80s Comedies
No Preview
10 Actors Who Cry All The Time In Movies
No Preview
Whatever Happened to All the Actors from the Movie Parenthood?
No Preview
The 10 Best Jon Stewart Daily Show Moments of All-Time
No Preview
Whatever Happened to The Cast of Beverly Hills 90210?
No Preview
Where Are They Now? The Cast of One Tree Hill
No Preview
10 Reasons Why Kaitlyn Bristowe and Shawn Evans Will Never Make It