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.
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!
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.”