Whether or not Brad actually had a serious relationship with these leading ladies is something only he could tell you, but regardless, take a look inside the Allied actor's little black book to see who has been lucky enough to have (supposedly) fallen under his spell.
They had actually been dating a few years when he guest starred as her love interest.
Sparks flying: Brad and Angelina pictured here in Mr And Mrs Smith.
In January 2005, Brad and Jen announced that they were getting divorced.
Eight months after finding himself single again for the first time in almost 20 years, Brad Pitt is taking his time before wading back into the dating pool.
The actor and father of six is understandably exercising caution, having just reached a tentative resolution in his temporarily acrimonious divorce proceedings.
Perhaps most of all, as he talked about in his epic star has been busy working on himself.