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.”
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.”
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.