The Women Brad Pitt Has Dated

Hollywood legend Brad Pitt has made ladies worldwide weak at the knees for over three decades now (yes, he really is that old) and has amassed quite a collection of notches on his bed post. In a romantic, flowers and chocolates kind of way, of course.

Long before Brangelina, one of the most well-documented marriages in Hollywood, Pitt was seen as a bit of a heartbreaker. From pop sensation Sinitta through to the one that made us all cry (Jennifer Aniston), check out our list of ladies who have been lucky enough to snuggle up to the Fight Club star.

Sinitta: 1984-1988


Way back in the early days of his career, Brad dated So Macho pop singer Sinitta. The pair were close for four years, with young Brad even escorting Sinitta to the 1988 Smash Hits Poll Winners Party. The couple remained close for some time before going their separate ways.

There does seem to be some overlap between the list of Brad’s lovers, so we’re not sure if Brad and Sinitta were on breaks or if Brad has been a little bit naughty (never!). Sinitta went on to have an on-and-off again relationship with music mogul Simon Cowell before finally marrying Andy Willner in 2005.