These two intrigue me for some reason. Maybe because they just don't seem to fit together? Or maybe that's just me.
For one thing, they're both Leos. Of course you don't judge relationships based on Sun signs alone, but they do have impact for sure. Two Leos together is definitely not a couple that you see a lot of. One of those Leos needs to be the star, so who's it gonna be? If one Leo is more introverted and one more extroverted it might be easier, but here we have two people who both are used to being 'the star', so I would think that could create friction. A fight to the finish you might say. Sean Penn was married to another famous Leo a while ago - Madonna. And we all know Madonna has to be the star.
Sean and Charlize are both super Leos in fact, as both have 3 planets in Leo each, and they both have Venus in Virgo.
So, what's the attraction? Usually in romances that take off fast and then break up quickly, we see hard aspects between Venus and Mars and Uranus, and sometimes Pluto. Uranus is exciting and unpredictable and fascinating. It's like being on a rollercoaster. You're up, and then you're down. Usually the excitement wears off quickly and then people break up. And yep, these two have some of that Uranus going on.
Sean's Uranus and Sun conjuncts Charlize's Sun, and also squares her Mars. That's excitement right there, and passion. Charlize has Mars in Taurus, which can be stubborn at the best of times and then Sean's Uranus Sun combo comes along and challenges that. When someone with Mars in Taurus is challenged, they just dig their little hooves in and refuse to budge. In the longer term, or after some of the excitement has died down a bit, I would think that he would drive her a little bit crazy because he would challenge her 'way of doing things'.
Her Neptune also squares his Venus, which is very romantic and heavenly for a while. He may be seeing her as an ideal of what he wants, but its largely based on fantasy. At some point reality sets in. Even more importantly, her Neptune conjuncts his Ascendant! He cannot see any of her flaws since Neptune blurs all of that. I would think he most likely has her up on a pedestal. This is a very romantic and floating on air kind of aspect - at least for a while. This can be very good for artistic collaboration too.
They have some good stuff, like her Moon in Leo on his Sun in Leo, and they both have Mercury in Leo which means they're on the same wavelength. His Jupiter also trines her Leo planets, which makes her feel good about herself and she feels supported.
Venus and Mars are the love and sex planets, and her Venus conjuncts his Pluto, which makes for hot sex. Her Venus squares his Mars, which again makes for intensity and drama in love and romance, but it is as aspect of irritation in the long run.
Charlize's Pluto squares his Saturn, and squares his Moon in Cancer. Sean's going to feel the brunt of that Pluto and could feel 'controlled' by Charlize. At the beginning of a relationship her Pluto hitting his Moon could feel quite thrilling and exotic, and emotionally intense. This could make for a lot of emotional drama between them, and battles of will as well. On top of the Uranian excitement, we have the drama of the Pluto.
Charlize has only one planet in the water element, and that is Saturn. I've always got a bit of a frosty vibe from her, so this explains a lot. Low or no water element means there is not a lot of comfort in the emotional realm, and with Saturn as the only planet in water, the water energy has to siphon out through Saturn, which could make her rather emotionally repressed. This wouldn't sit well with Sean who has his Moon in Cancer. He wants to be nurtured and babied and to feel very emotionally secure. Her Saturn in Cancer is in the same sign as his Moon, but they're not quite conjunct. Still, being in the same sign means they will still feel the energy. Sean has a Moon Saturn opposition natally, so he never felt that he got the kind of nurturing that he needed from at least one of his parents. So, he is replaying that aspect out again by finding someone who's Saturn hits his Moon - amplifying his natal aspect. He again may feel that he's not getting the kind of nurturing or emotional support from Charlize that he really needs. She's more of a 'deal with it and carry on' kind of person I would think. I do know she had a horrific childhood in that she witnessed her alcoholic father physically attack her mother and threaten both of them whilst drunk, and then her mother shot and killed her father in self defence, Her mother faced no charges. No wonder she was drawn to a man with rage issues - sort of re-creating her childhood. Her Saturn in Cancer makes sense here as well, where she herself was denied some nurturing as she grew up and as she had to deal with an alcoholic father. Actually Saturn in Cancer (her) is very similar energy to Saturn oppose the Moon (him). They likely both felt a lack of nurturing or emotional security when younger and that could be one of the shared bonds between them.
Saturn always shows what we take very seriously. In Cancer, she takes emotions very seriously, which actually gives her an edge as an actress. She has won numerous awards and it shows that she can make a career (Saturn) out of acting emotional (Cancer).
According to the Magi, there must be some strong flowing Chiron aspects between two charts if people are to be in a happy long term union or a marriage. They have one decent Chiron aspect - her Chiron contra-parallels his Neptune. It's not perfect as its a contra-parallel (similar to an opposition), but it does speak to the fantasy and romance in the relationship.
Sean's infamous anger issues can be seen with his feisty Mars square volcanic Pluto and Venus. Charlize's Venus triggers it, so at first she may seem like a soothing balm on his anger, but its still a trigger. Plus, her Mars squares his Sun Uranus conjunction - so she can trigger his anger.
Right now Jupiter is conjunct Sean's Mercury, which rules his 7th house of relationships. He's feeling good about things right now. In fact, early 2015 looks pretty good for both of them with Jupiter hitting their Leo planets. Mid May 2015 is when they hit a rough patch though, and then in November Saturn will square their composite Venus, which is not a happy time.
This will be interesting to watch!
Update - June 2015. The word is that they already split in mid May due to Sean's anger issues. Check out new post Sean and Charlize broke up in May