First of all in looking at their charts, one can’t help see how they would have a strong and very deep connection to each other. Jennifer’s Sun closely conjuncts Brad’s Moon in early Sagittarius (using Vedic-sidereal positions). Their Jupiters oppose each other, which is a great mutual position for Jupiter between two people. Jennifer’s Venus conjuncts Brad’s Jupiter, and Brad’s Moon/Venus conjunction trines Jennifer’s Pluto. Love and affection could not NOT flourish under such configurations; they would feel deeply connected and would always derive vibrant, luminous energy from each other.

Brad and Jennifer could act compulsively to be together in an extremely vicarious way, only to then see each other as the worst monster of their own projected psyches. They could act in domineering and controlling ways to each other, or be cruel. Their physical excitement they feel with each other could turn into anger and become verbally heated or worse.

One would hope that such a couple could get on top of the lesser sides of their relationship dynamics and let it become a mutual vehicle for world service (even in the entertainment industry) and personal spiritual victories.

Jennifer herself is Libra rising, always preferring and striving to create harmony in the environment; balance and poise is her preferred style of being. Fiery and turbulent Aries rules her seventh house of marriage partners, and Mars itself (her seventh house planetary ruler) is very strong in Scorpio but conjunct Neptune. Jennifer requires a very strong, if not "misunderstood" kind of figure as a spouse; who would be sometimes lost in another world (which is an actor’s profession btw), or somehow involved in abherent psychological deceptions or escapist tendencies. A man that Jennifer might attract/magnetize into her life could also have a tendency to be deceitful or involved in passive-aggressive behaviors.

Jennifer’s private home/domestic life (which is a very important part of relationship delineation) is ruled by trouble-prone Capricorn on the fourth house. Saturn as the fourth house ruler falling in her malefic sixth house adds to the friction she would feel. Jennifer may have an inborn tendency to look at things negatively, especially with regards to emotional matters and that may color her relationships.

Brad as an intense Scorpio rising individual, almost the brooding time-bomb sort of archetype; has lovely and sensual Taurus on his seventh house cusp of marriage signifying Jennifer. Brad is intense and he may take aggressive advantage of others even if just to satisfy his own desires.

The planetary ruler of Brad’s seventh house of marriage is Venus, and in his chart Venus falls in Capricorn. We have already mentioned Capricorn’s tendency to darken or cast difficulty wherever it is; but we also need to remember that Venus itself is not that badly off in dignity in Capricorn. Therefore Brad might have a compulsive need to intensely be in relationship situations, even to experience a vigorous exercise of power; but he’s got the wiring for long-term happiness and stability in relationships.

Brad does have three planets in Sagittarius so he may really need his personal freedom and that can be a hindrance to long-term relationship success. Brad would appear to have conflicting personal issues competing for dominance in his psyche.

Tremendous forces are at work on this relationship, hopefully pushing them to make mature psychological progress, or else maybe exerting damage that would be practically unrepairable. This action is being instigated by unsubtle influence of transiting Pluto conjunct Brad’s Sun and Jennifer’s Moon; this Sun/Moon configuration is perhaps their deepest connection.

It should be noted that Brad’s career appears to be expanding and growing now more than ever with almost no end in sight. He has just entered into a new Jupiter major dasa (period), and his Jupiter is positioned very strongly in his chart. Is he now "going to the next level" and therefore Jennifer has to "step aside?".  

With the divorce now final, and Brad definitely having hooked up with Angelina Jolie; Brad and Jennifer have indeed gone their own ways.  In the near future look for a Brad Pitt/Angelina Jolie article here. 

Jennifer seems poised for success also having recently entered her Moon dasa. The Moon in her chart rules career, success, and reputation; and is relatively well fortified. An aspect from Saturn however onto her Moon could indicate some turbulence and working out of things to come during this dasa period of ten years that started in 2001.

Maybe just maybe in the year 2011 as Jennifer enters a new Mars major dasa new relationship/marriage possibilities will arise, since Mars is the ruler of Jennifer’s seventh house of marriage. We will see.