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.
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.
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.