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.
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.
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.