In-Depth Analysis Of Brad Pitt’s Love Life
Andrew Parker - July 23, 2019

The latest rumor has it that the dreamy heartbreaker, Brad Pitt was last seen with Charlize Theron.  And apparently, the two were actually introduced by her ex, Sean Penn.  There’s never a dull moment or shortage of drama when it comes to Hollywood! Regardless if this is true or not, one thing is sure: Pitt has gone out with some of the most beautiful and talented A-listers in the industry, without having one specific type. Here is a breakdown of his relationship timeline, or at least the ones he made public, even before the whole Brangelina scandal.


Started With The Flings



Hollywood actor Brad Pitt has had more flings that we can count on our fingers, and also probably more than most of us will ever have too. The super hunk dated Sinitta, the talented singer and good friend of Simon Cowell. The good looking pair showed up at the Smash Hits Poll Winners Party together back in 1998, pictured here looking as stylish as ever.  The two were on and off again for quite a while, four years to be exact. 


And So They Continue



One of the most notable of his short-lived flings, perhaps since they looked so good together, or due to the way in which she left him, was with blonde bombshell actress Christina Applegate. She is known to have left him in the middle of the MTV Movie Awards for another guy, however, she refuses to admit who this very lucky guy was.  According to Sebastian Bach, it was him, but nothing has been confirmed until this day. 


Then Came Gwenyth



Other than his infamous relationships with Jennifer Aniston and Angelina Jolie, Pitt is also well known for his relationship with the charming and comical Gwyneth Paltrow that started out in 1994.  The pair met on the set of the film Se7en, and in 1996, were already engaged. When they broke up, Paltrow’s father was completely heartbroken about it, claiming to have loved Pitt just like his own son. Nonetheless, they were one of the most it couples of the ’90s.


But Then Came, Jennifer



His long term relationship with Gweynth was followed by his marriage to the one and only, the drop-dead gorgeous and undeniably talented Friends star – Jennifer Aniston.  After being set up by their acting agents on a blind date in 1998, they become one of Hollywoods most iconic and unforgettable couples.  The celebrity pair got married at an elaborate ceremony in Malibu, California in 2001. Guests included Courtney Cox, Cameron Diaz, and Salma Hayek.


The Fairy Tale Didn’t Last



The fairytale marriage between Brad and Jennifer, unfortunately, didn’t last past 2004, after Brad fell for his co-star, Angelina Jolie while filming Mr & Mrs Smith.  This caused a great deal of controversy, with fans showing their loyalty and taking sides either with Aniston or Jolie as you all surely remember.  Brad even admitted to the press that he felt as though his marriage with Aniston felt like it was pretending to be something it wasn’t.  


Brangelina Begins



The couple went on to have six children together, three of which they adopted. It took them quite awhile to actually get legally married, due to their strong beliefs about equal marriage, and wanting to wait until everyone would be given the same rights.  Jolie filed for divorce from Pitt in 2016, and in 2019 it was officially finalized. Their highly publicized relationship lasted for an impressive (in Hollywood, that is) twelve years.


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