Leave it to Penn to move from one amazing woman to another, just as he did when he began dating supermodel Petra Nemcova in 2008 – or at least, that’s what the reports said. At the time, he and former wife Robin Wright were taking some time apart and had mutually decided to see other people. Nemcova is another strong-willed woman, which seems like Penn’s type.
Just ask his former girlfriend Shannon Costello, who actually worked as the director of communications for his Haitian relief charity organization. Penn and Costello were together for a short while after his split with Scarlett Johannsson.
A-List Couple Ups
Sean Penn has been known to romance some of the biggest names in the business. Penn has dated Charlize Theron, Madonna, and Robin Wright, just to name a few.
The star definitely has a penchant for highly regarded actresses and models. Read on to explore the ups and downs of Penn’s personal life and see just what we mean.
Super-speed Superstar
Penn seems to almost have supernatural abilities when it comes to snagging himself gorgeous women. He also seems to move very quickly, as far as hooking them is concerned. Just look at him waiting for swimsuit model Jessica White to leave the car.
When was he with Ms. White? Oh, pretty much right after he split with his former wife, Robin Wright. Apparently, things move quickly in Sean's love life.
Yes, He Can
Even though Penn is notorious for moving through women as if he moves through roles, he actually is capable of committing. Penn decided to tie the knot more than once, along his rollercoaster love life.
The first time Penn would put a ring on someone’s finger, it would make major headlines. But little did the press know that this would be the beginning of a major media storm for Sean Penn and his new bride.
Do I?
Everyone who hasn’t been living under a rock for the past decade or so knows who Sean Penn was first married to Madonna. The couple originally met back in 1985 and dated for just 7 months before they made it official. They were going strong for a while, while they were the “it” couple in Hollywood.
Everyone wanted to see them make it forever. Unfortunately, some life-altering news would hit the stands that would change everything.
Back In The Day
But what was Sean Penn up to before he took the plunge with Madonna? Well, in his past, he was extremely dedicated to his relationship with the beautiful Elizabeth McGovern. When they were together, he really thought she would be the one walking down the aisle with him. The couple fell in love while working together on Racing with The Moon, and he very quickly got down on one knee.
Of course, she was so excited by the thought of being married to THE Sean Penn that she said yes. However, not long after she had a change of heart. She told him that she was “too young,” and she wasn’t ready to make that kind of commitment at that time. Later she would say that she was “lucky,” for making that decision.
Setting the Bar High
Just when it seemed as if Penn was only interested in actresses, he decided to shake things up a little bit and get involved with Australian model Elle Macpherson.
They were spotted canoodling at an Upper Eastside restaurant in NYC, in 1996. One onlooker described the pair as only having eyes for each other, and very physically affectionate towards one another.
Romantic Rumors
In 2009, Sean was spotted with the gorgeous and intelligent Natalie Portman, at the bar inside of the Sunset Tower Hotel. Apparently the two were trying to enjoy a quiet dinner, but they kept being bothered by all of the agents of the press, who were understandably excited about seeing them together.
However, Portman later told E! Online that the rumors about them being romantic were just that – rumors.
Addressing the Gossip
Portman, who admitted that she typically doesn’t even acknowledge, much less respond to, rumors about her romantic life – had something to say about this whole thing. She flat out told reporters that the entire story about their being something between her and Sean was “fabricated.”
But the press just couldn’t let it go, and they kept trying to spin everything to make it seem as if the two were dating. One anonymous source in Hollywood jokingly said that Portman, at 27, was, “far too old,” for a star of Sean’s age (48.)
Sean & Robin
Actress Robin Wright, who is well known for her role as Claire Underwood on House of Cards, started dating Sean right after his split from Madonna. The two actually dated for a long time before he decided to pop the question – undoubtedly because rushing in to things didn’t work out so well for him the first time around.
Luckily, he and Wright ended up having a wonderful stint of marriage, during which they had two beautiful children.
Far from a Fairytale
Dylan Frances was the first of two children of Sean Penn and Robin Wright. After having their first daughter, the two then brought Hopper Jack in to the world. Everything seemed like a fairytale, like it would last forever. They seemed so happy and it just seemed like all was well – but all good things must come to an end.
Things just started to happen, and little things turned into big things. The happy couple’s dream life would soon come crashing into a harsh reality that would shatter everything.
Harder Than It Looks
Although Wright put on a happy face for the world, when it came to her marriage to Penn, she eventually told reporters that not everything was as wonderful as it may have seemed. She was quoted as saying that the marriage was, “difficult,” at times. Soon after the two tied the knot, things just started to spin entirely out of control.
Bad At Love
One of the worst things about breaking up with someone, and especially getting divorced, is reflecting on the relationship and having all of these distressing thoughts about if the other person really ever even loved you. Apparently, this is something that keeps Penn up at night.
He has been quoted as saying that he feels as though no one he’s been with in the past really loved him. This kind of self-destructive thinking can really do a number on someone’s mind. Penn told Esquire magazine that he considers this to be a, “fantastically strong humiliation.”
Playboy Lifestyle
Penn’s superstar status means that whenever he gets out of one relationship, he can pretty much jump right into another any moment he chooses. So, when he got back out on his own, he was understandably playing the field. And what better place to pick up women than at the bar? Penn started going out and drinking for, “nights in a row.”
A Change of Heart
Penn started to make some serious changes to his life, ultimately beginning with himself. After his divorce, he started searching for anything that might make him feel like his life had some meaning. He said that he was tired of just lying in bed being upset all of the time, and he was watching everyone around him get involved with philanthropy.
One day, he happened to turn the TV on to a story about a major earthquake in Haiti. Learning about this disaster, coupled with good timing, led Sean down a path into becoming involved as a philanthropist.
Journey For The Self
An anonymous source that is close to the superstar told one reporter that Penn, “used to drink a lot,” and that the drinking “got him in a lot of trouble.” Sean was searching for something that could fill a void that was left from his divorce, and he got really involved in disaster relief in Haiti. Once he did this, it really seemed to provide a good outlet for him.
He got more and more involved, and people around him started to notice a lot of positive changes. Penn actually started up his very own non-profit organization – the J/P Haitian Relief Organization. He was even able to begin a slight friendship with Madonna once he began to turn his life around.
Still Searching
Penn put a valiant effort into looking for someone to make a real connection with. He felt as though he kept taking a swing and missing, so to speak. He wore his heart on his sleeve during an interview with Esquire magazine, in which he said that he had “no shame,” in admitting that everyone just wanted “to be loved by someone.”
He even went so deep into his feelings that he referred to some of his past relationships as being full of “fraud.” Once he felt that he’d been cheated out of true love one too many times, he started searching for his soul, instead of his soulmate.
The Crown Jewel
Penn and his former wife Robin Wright seemed to be on a romance rollercoaster, which was full of ups and downs. This means that there were periods of time during which the two wouldn’t see much at all of each other. They ended up coming to the conclusion that it would be beneficial for both of them to date other people.
During one of these “off,” periods with Wright, Penn was reportedly dating singer and musician, Jewel. The timing of this just so happened to line up with when Penn directed one of the star’s music videos. Later, Jewel would publish a book in which she describes falling head over heels in love with Sean.
Ulterior Motives
When Jewel was a rising star and was only about twenty years old, she was living with her mom and dad when her house phone started ringing. Her dad answered and, apparently hung up in disbelief as Penn asked to speak to his daughter. “He hung up on him several times,” she told Access Hollywood.
When he finally got through to her, it was to ask her to write a song for his movie, The Crossing Guard. Things really started to escalate from that point for the young Alaskan beauty, as she grasped the incredible opportunity that had just come her way.
About A Boy
In her interview with Access Hollywood, Jewel describes Penn as being, “all about the business,” when they first made contact. But of course, Jewel was a young woman in L.A and Penn was, well, he was Sean Penn. She couldn’t help but to develop a crush on him, even in the beginning. She admitted that she had always admired that he was very, “sharp and sweet.”
It also doesn’t hurt when you feel like someone that you admire sees your potential and encourages you to follow your dreams, and that is exactly how Sean was with her. Not to mention, he was flying her out to all kinds of exotic locales and introducing her to other mega-stars.
Big Dreams
At a time in Jewel’s career when she was just starting out, she was understandably a little nervous and was reaching out to Sean for support. She felt very lucky to have this incredibly talented star in her corner. The relationship that these two have may not have been a life-altering or extremely impactful relationship for him, but it meant a lot to Jewel to have Sean believe in her when “no one else did.”
Jewel apparently really did love and look up to him, and he felt that which is why he enjoyed spending his time with her.
The "It" Couple
In 2011, things in Penn’s love life got ramped up a couple more notches when he started dating superstar Scarlett Johansson. Penn was photographed with Scarlett many times, including one picture of the pair where Johansson played footsie with him while dining at an upscale restaurant.
Each of the photographs seems to portray a pretty intense, yet laid-back romantic vibe going on between the stars. Penn and Johansson even accompanied one another to the White House Correspondent’s dinner that year. But things didn’t exactly end up going very far between the two, and Penn reportedly cut things off with Scar-Jo not too long after.
Freeze Frame
Sean is no stranger to the way things work around Hollywood. He obviously knows that the press loves to spin stories, especially ones that put A-listers together in the world’s view. But Sean started taking steps to actually avoid Scarlett when the pair’s casual romantic episodes came to a halt.
One time on the red carpet, a photographer was lucky enough to catch them in the same vicinity and asked them to take a picture. Scarlett happily agreed, much to Sean’s dismay, and they were portrayed as being an item once again. Apparently, Sean’s efforts to avoid Scarlett that night by sneaking in the exit didn’t really pay off as he’d hoped.
Master Actor
Acting is a profession that requires its dedicated servants to wear a million masks. A good actor will portray their character so believably that the audience feels like they truly know the person in whatever movie or show they’re watching.
Unfortunately, this often means that when a fan gets to meet the “man behind the mask,” their hopes and dreams are shattered. This is basically what happened when Sean started to have all sorts of episodes in the public eye – especially when it came to light that he’d been physically abusive towards Madonna.
Jail Time
Penn’s hateful attitude towards the paparazzi is definitely no secret, not even from his biggest fans. In one of the most famous outbursts that happened in 1987, he was on set when he violently attacked a photographer.
This crazy, but not uncharacteristic, event landed him in the slammer for a little over 30 days – half of his court ordered sentence. Not too long after this, Madonna would file for divorce, but would withdraw the papers before they were pushed all the way through.
Questions Abound
In early 1989, a tabloid newspaper called The People, would put out an article that shocked the public to their core. Not only did the piece claim that Madonna was brutally beaten by Penn, but that he did things that made him sound like a complete sociopath. The article claimed that Penn tied Madonna to a chair, in the midst of the abuse. This type of information being linked to Penn truly confused his fans.
The behavior being described seemed so far away from anything they’d seen from Penn before, and they really didn’t want to believe that he had it in him to act this way. But according to the article’s author, Peter Kent, the reports were verified by law enforcement officials in Malibu.
The Breaking Point
The way assistant staff described freeing Madonna from that situation in the report didn’t make matters any better for Penn. The article portrayed Madonna as being seriously distraught, with horrible marks all over her face from where he had hit her. One staff member claimed that poor Madonna’s mouth was actually “frothing,” when they found her.
According to Kent, Penn’s publicist pushed the incident under the rug, attributing it to “regular young couple stuff.” Even though it was all very far from the truth, it would prove to be the breaking point.
Private Affairs
After the alleged incident involving the chair, Madonna appeared to give Penn another chance. They carried on the relationship for a short while after, until Madonna filed for divorce again. But unlike the last time she had filed, when she withdrew the papers, she put her foot down and made sure everything went through.
Several reports speculate why the marriage was ended, but Madonna never really cleared things up for the public. She told reporters that there were some things the pair would like to keep private.
False Reports
After the lengthy and very graphically detailed report put out by Peter Kent about how Penn had allegedly beaten Madonna, their relationship did in fact come to an end. But Madonna would later come to Penn’s defense when she told Entertainment Tonight that Kent’s report, and any reports that stemmed from it, were “entirely outrageous.”
She would go on to say that the reports were completely false. The two may have ended their romantic relationship, but they would later be able to cultivate a friendship after putting their troubled past behind them.
She's The One
When the holidays rolled around in December of 2013, Penn set his eyes on a new leading lady, and entered into a romance with the beautiful and talented Charlize Theron. This pairing seemed much more serious than some of his previous endeavors, such as his fling with Scarlett Johannsson, and rumors began to circulate about the two A-listers tying the knot.
But was there any truth to those rumors? Apparently, yes, as Sean confirmed the two were in fact, engaged. Penn very much wanted things with Theron to work out and was quoted as calling her the, “love of his life.”
Broken Hearts Club
Just as Sean felt that Charlize Theron was “the one,” she publicly went on record to say that she felt the same way, and that she was “lucky,” to have him. The two had been dating for 18 months when they announced they were engaged to be married, but things didn’t exactly pan out the way they were hoping for – at least, not for Sean.
Things between him and Theron started to become shaky, and eventually, the superstars went their separate ways. There were no hard feelings between the two, at least according to the public. Charlize brushed the entire thing off, saying that their relationship just, “didn’t work anymore.”
Sean's Side Of Things
Charlize may have been able to just brush her relationship with Penn under the rug when she was over the whole thing, but Sean was devastated by the split. Sean reported that Charlize basically just ghosted him and stopped answering his calls.
Apparently, the two were on much different pages about their relationship, as Sean seemed like he wanted to make things work and Charlize just wasn’t having any of it. Sean was quoted after the breakup as saying that she simply “cut him off.”
Mixed Feelings
Even though the marriage between Sean Penn and Madonna didn’t last for an incredibly long time, doesn’t mean the two didn’t grow extremely close while they were together. So close, in fact, that rumors of the couple planning to get remarried started swirling around.
What surprised everyone even more than that fact itself, was that it was indeed Madonna who vocalized the want to remarry. Madonna is known to have quite a mind of her own, but this was really just shocking – even for her!
Money, Money, Money!
Madonna has been known to be very involved with charity, including attending all sorts of galas to show her support for various causes. One of these gala’s happened to be the Miami Art Basel charity gala.
Madonna and her former husband took to the stage, when Madonna turned the room upside down with a very unexpected announcement. She told everyone who was in attendance that she would definitely date Sean again.
Sweet Memories
This announcement shocked all of the A-listers in the audience at the charity event. Celebrities such as Leonardo DiCaprio were left with their jaws on the floor. The shock level continued to rise as Madonna auctioned off all sorts of her items to raise money for the charity.
Patrons Of The Arts
Madonna was extremely passionate about the Miami Art Basel gala. She was so excited for the evening that she kept hyping it up to everyone as an affair of art, music and “mischief.” She had really hoped that by doing all of this, she would light a fire under the A-list guests to spend all of their money towards charity that evening.
Belle Of The Ball
Madonna has long been admired for her bold fashion choices. She was having a hard time choosing just one outfit for the gala and instead, brought along several to change in to throughout the evening. For her explosive scene with former husband Sean Penn, she opted for a short, puffy skirt and a shimmering corset that really accentuated her beautiful features.
The moment between the two stars really pulled on the heart strings of all of those who wanted so badly to see them back together. Luckily, everyone got to see what they wanted, if only for those few moments they spent on stage that evening…or was it?
The Catch
And all along, while the A-list audience members had their hopes of seeing the golden couple back together, there was a catch. Madonna shocked the audience by telling Penn that she would absolutely remarry him right then and there – IF he dropped 150,000 dollars on one of the necklace’s up for grabs in the auction.
Penn was certainly caught off guard a little bit, but since the two had a fondness in their hearts for one another, he was a good sport about the whole thing. In fact, Penn actually agreed to spend the money on the necklace and take Madonna up on her offer! But then, something occurred that would change everything.
Dance Party
Before Penn could even get the words out of his mouth that he’d take her up on the strange proposal, Madonna decided to take the performance in another direction. The bridal waltz came over the loud speakers and Penn found himself in an awkward situation on stage. Madonna shimmied and shook all over stage in some kind of an impromptu not-so-private dance.
Penn may have been okay with this, had it not been in front of all of the eyes in the audience, including Madonna’s eleven-year-old son, David. But the fact that her son was there didn’t stop Sean from whipping out a pair of handcuffs and taking the steam factor up even more.
Think Of Anything?
Madonna pulled the audience in through the power of her voice as soon as Penn slid the handcuffs on to her wrist. She leaned in to the microphone to tantalizingly joke about the “many moments,” of their marriage. The audience laughed, of course, everyone knowing that she was obviously referencing the media circus created by the false reports.
The same media circus that apparently isn’t the reason that the pair split at all. They joked and laughed and looked cozy in one another’s company, all while raising money for charity and keeping the audience very, very entertained!
Turning Red
The temperature was rising through the roof at the gala and the audience members were at the very edges of their seats. People were chewing on their finger nails in anticipation of what Madonna and Penn were going to do next. Imagine everyone’s surprise when the sultry blonde singer leaned in and whispered in to her former husband’s ear that she was in love with him still!
It wasn’t just the audience that was surprised by this, as Penn had a look of bewilderment on his face, too. And just when he thought things couldn’t get any more intense, he turned around to find old pictures of them from their former life as a happy couple displayed on a large screen behind them.
Friend Zone
Even though it was all purely speculation, many publications were insistent that Penn and Madonna were nothing more than friends at this point. But with Madonna making moves like what was happening onstage that night, everyone was left wondering if there was any truth behind those rumors, or if they were in fact getting back together right before their very eyes.
After the wonderful reunion in front of the gala crowd, Penn’s was outbid, although his offer was very generous. But after that sultry performance, plenty of other big spending Hollywood gentlemen in the crowd that wanted to get their hands on some of Madonna’s stuff!
The List Goes On
Leave it to Penn to move from one amazing woman to another, just as he did when he began dating supermodel Petra Nemcova in 2008 – or at least, that’s what the reports said. At the time, he and former wife Robin Wright were taking some time apart and had mutually decided to see other people. Nemcova is another strong-willed woman, which seems like Penn’s type.
Just ask his former girlfriend Shannon Costello, who actually worked as the director of communications for his Haitian relief charity organization. Penn and Costello were together for a short while after his split with Scarlett Johannsson.
Young Love
Sean went through a period in his life where he was rumored to have been dating Vincent D’Onofrio’s 20-something year old daughter, Leila George D’Onofrio. Leila was this gorgeous, super talented young woman and Penn was, well – Penn. When he decided that he wanted to pursue someone, he went for it. As was the case with Leila, when the two were working together in the studio on a new audiobook she was going to put out.
The gorgeous young singer snapped a shot of herself with the A-list playboy that day and posted it to her Instagram. Leila would later go on to join the acting side of Hollywood after she worked with James Franco in Mother, May I Sleep with Danger.
Night Out
Penn was at it again, according to what an anonymous source divulged to US weekly, when he was seen dining out with beautiful young actress Minka Kelly. But according to the source, the two weren’t alone on their dinner date – they were accompanied by a mutual friend, that had apparently known both parties for quite some time.
But why was this 3-person dinner date so odd? It could have been the timing, as it happened pretty quickly after his devastating split from former fiancé Charlize Theron. The source made sure to tell the magazine that it definitely was a “date,” but it was also a “group setting.”
What On Earth?!
An unexplainable scene unfolded in NYC, in May of 2017, which caught passerby’s and the press entirely off guard. Dylan, the daughter of Penn and former wife, Robin Wright, was dating Jimmy Giannopoulos at the time of the event. Dylan’s parents were having a nice meal with their daughter’s boyfriend at a café in the city, when things took a seriously unexpected turn.
Penn and Jimmy seemed fine in the restaurant, but then apparently, they decided to “take things outside,” and everything went downhill from there. An explosive argument took place between the two men, and according to a nearby source that spoke to Radar, Penn was shoving his phone in Jimmy’s face and yelling at him about something that was on the screen.
Not Seeing Eye To Eye
Penn’s critics would be the first to say that this kind of behavior is actually pretty characteristic of the star, but his fans may have some issues with that. Whatever happened between Penn and the young musician at the NYC café, the situation seemed to escalate pretty quickly.
The source described a very emotional scene occurring between everyone involved, including Robin who was allegedly crying, as Penn had an outburst and Jimmy stood there with a hand over his mouth, not wanting to egg on the troubled actor. Luckily, the three worked out whatever it was, because they were all seen embracing before leaving.
Spilled Tea
Saucy Mexican actress Kate del Castillo, who is most well recognized for acting on Muchachitas, the telenovela, has some history of her own with Penn. But reportedly, that’s some history that she wants to put much further behind her. Kate and Penn did some traveling together in 2015, when they headed off to Mexico.
Kate has claimed that while in Mexico, she met the infamous drug lord – El Chapo. This could all be pure speculation, but she has offered to go in to more detail of the time she spent in Mexico, since Penn allegedly made some shady moves against her career.
Rock Blocker
Castillo was apparently working on a documentary series that she was hoping would air on Netflix when, according to her, Sean heard about what she was trying to do and made the decision to effectively close off that avenue of income for her. Understandably, this pushed Castillo to work even harder towards her three-part film series.
Penn would have played a very large part in the documentary, as according to Castillo, she would give a detailed account of exactly how she fell in love with him, and how their elusive romantic relationship played out.