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. He's not wining and dining fellow A-listers at paparazzi-magnet hot spots, or otherwise going on splashy outings. He'll get back out there eventually, but after what he's been through, it feels safe to guess that he'll keep any new romance close to the vest. 

Perhaps most of all, as he talked about in his epic GQ Style interview, the War Machine star has been busy working on himself

He's focusing on promoting his new movie and reconnecting with friends. He quit drinking, he's enjoying therapy, he's making art... Basically, Brad's dating Brad right now.

Perhaps he's also wondering whether dating has changed at all in the two decades since he's been on the market. The answer of course being, "yes, yes, it has"—though probably not all that much if you're Brad Pitt.

He was busy then and, if he so desired, he could be busy now.

That's right, before getting married for the first time in 2000, Pitt was almost never alone—and thanks to the 1980s and '90s being a less jaded time, a time before every celebrity couple had a hashtagged nickname, there's plenty of photographic evidence. So if your historical knowledge of the matter starts and stops with Jennifer Aniston and Angelina Jolie, here's your encyclopedic guide to Brad's rather epic dating history.

Sinitta, Brad Pitt


Brad Pitt, Shalane McCall

Jim Smeal/WireImage

Brad Pitt, Jill Schoelen

Ron Galella/WireImage

Robin Givens, Brad Pitt

Vinnie Zuffante/Archive Photos/Getty Images

Christina Applegate, Brad Pitt

Barry King/Getty Images

E.G. Daily, Brad Pitt

Barry King/WireImage

Geena Davis, Brad Pitt

Time Life Pictures/DMI/The LIFE Picture Collection/Getty Images

Juliette Lewis, Brad Pitt

Ron Galella/WireImage

Thandie Newton, Brad Pitt

Getty Images

Jitka Pohlodek, Brad Pitt

Jim Smeal/WireImage

Gwyneth Paltrow, Brad Pitt

Barry King/WireImage.com

Claire Forlani, Brad Pitt


Brad Pitt, Jennifer Aniston

Gregg DeGuire/Getty Images

Angelina Jolie, Brad Pitt, Cannes

Pascal Le Segretain/Getty Images

It doesn't take a chemistry degree to figure out why Brad didn't seem to have any trouble finding dates from the moment he arrived in Hollywood.


The late '80s alone for him would make up the entirety of most people's entire dating portfolio.

Of course he's matured and experienced a lot of life over the years, and his must-haves in a partner have evolved ("likes and gets along with children" is presumably way up there now). And with all that perspective, the last thing he wants is a driving-up-and-finding-Mike-Tyson-waiting level of drama.

But once again, Brad Pitt is a most eligible bachelor.

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