Sandra Bullock’s chart is not a very emotional one.  She has the Moon in reasonable and rational Aquarius, showing that her feelings (the Moon) tend to be filtered through the mind rather than the emotional body.  She has very little other water in her chart other than Saturn in Pisces, which shows a discomfort and fear (Saturn) of losing herself (Pisces), and Chiron is also in Pisces showing a wound (Chiron) in that same area.  

In addition, with Venus (relating) in the changeable sign of Gemini, she is likely to need  a lot of space and air in her relationships.
Chiron, the wounder and healer, is in a challenging square to Venus in Sandra’s chart which suggests that relationships are for her the greatest teachers but can sometimes lead to emotionally wrenching experiences.  

Sandra met Jesse James in December 2003 when  transiting Pluto (transformation and compulsion) formed a challenging square to Chiron in Sandra’s chart and began to set off the Chiron/Venus system.
Pluto transits call us deeper into the soul where we have to face parts of ourselves that have long been hidden, and Pluto transits to Venus also bring about intense relationship experiences that can be very difficult but which in the end teach us something about ourselves.
Pluto transits to Chiron often have the effect of healing a deep wound within us, but can also serve to expose that wound so that it can be dealt with. 

 For the two years that Sandra and Jesse were dating, Pluto was engaged in this dance with Venus and Chiron in Sandra’s chart, stimulating her desire to heal (Chiron) her relationship issues (Venus).  Sandra was also in her “Neptune Square” between 2004 and 2005 during their relationship.  The Neptune Square occurs when transiting Neptune forms a challenging square to Neptune in our chart at around age 40-43, a planetary cycle that often creates confusion and the potential to be deluded (it also brings us more deeply into a spiritual life if handled properly). 

 When Sandra and Jesse married in July 2005,  she was in the middle of not only the Neptune Square, but also the Uranus Opposition (when transiting Uranus is opposite Uranus in the natal chart, stimulating rebellion and the desire for change).  These two cycles occur at the same time for everyone, making the early 40s a huge time of change and potentially chaotic.  The fact that Jesse James was different than anyone else she had ever dated (Uranus) and somewhat mysterious with a dark past (Pluto), as well as exceedingly romantic (Neptune)  made him an ideal candidate for this phase of Sandra’s life. 

 I can’t say I haven’t made similar choices in my own life, but I am happy to say that every bad choice I made helped to prepare me for the healthy relationship I have now.  The mistake we make is in believing that our detours are errors instead of seeing them as learning experiences.  Of course this is much easier to accomplish when you’re not living in the goldfish bowl of Hollywood celebrity.