Ahh, Brad Pitt. Academy-award winning actor, philanthropist and s*x symbol, regarded as the most attractive man in the world by countless publications. With titles like that, it is not surprising that Pitt has been with a significant number of women, a number even larger, given that his career in the industry has spanned three decades. But, don’t get it wrong: it hasn’t been all rainbows and sunshine for Brad Pitt. A former flame once commented on his sub-par bedroom skills (ouch) and he was also left mid-date for another man (again, ouch). Despite the fact that Pitt managed to steal the heart of one of the most beautiful women ever, he has also had his fair share of heartbreaks.
The man was a serial dater back in the late 80s and 90s, dating woman after woman after woman. It is accurate to say that he has casually dated many more woman than he has invested in long-term relationships. But, of course, we are talking about Brad Pitt, so that is to be expected from a man who can likely charm just about any woman he meets.
He has had a number of high-profile relationships as well, just what you would expect from a Hollywood sex symbol. Interestingly, he also has a rather large number of engagements and has been married twice. There you have it, ladies and gentlemen: Brad Pitt’s romantic history summarized in just a few words. What about his type, you ask? He does seem to fall in love with a ridiculous number of his co-stars. It is so excessive that it makes us question whether Pitt is able to separate on-screen romance with off-screen romance. He has dated the likes of Geena Davis to Christina Applegate, but let us not spoil the rest of the eye candy on this list. Just know that it doesn't appear that he goes for any particular looking woman - in fact, some of his choices are rather unexpected ones indeed. Here’s to the ones he's loved and lost.
17 Julia Ormond
14 Juliette Lewis
Obviously, sex symbol Brad Pitt has been with many, many women. However, according to Juliette Lewis, "He was no...big deal, if ya know what I mean!" which perhaps comes as a surprise to us all. However, this comment is not the most scandalous thing when it comes to this particular relationship. She was only 17 years old at the time while he was, wait for it, ten years older! What? This would not be, by any stretch of the imagination, a socially acceptable relationship. In other words, this is certainly a case of a man dating an underaged girl. In any case, Lewis managed to tie Pitt down for an entire three years back in 1990. In a throwback picture on Instagram in 2014, Lewis wished Pitt a happy birthday to her “old friend.” She went on to write that "[Pitt] taught me so much as a wee youngster.” We’re sure he did, Lewis. We’re sure he did.
13 Geena Davis
Here we have one of many cases of Brad Pitt falling in love with the woman he kisses on screen. Geena Davis and Pitt reportedly dated for an entire year but they kept it a secret the entire time. Although their relationship can’t be 100% confirmed, Davis definitely had a thing for Pitt while filming Thelma and Louise, even stating that she often messed up her lines because of his good looks. Even more, while they actually hired a female body double for the now famous love scene, Davis wasn’t having any of that.
12 Jill Schoelen
11 Elizabeth Daily/E.G. Daily
10 Christina Applegate
9 Claire Forlani
8 Shalane McCall
7 Robin Givens
6 Gwyneth Paltrow
5 Katja von Garnier
4 Demi Moore
3 Jennifer Aniston
Brad Pitt and Jennifer Aniston were married for five years, and together for seven, until the relationship reached its inevitable end in 2005. Since then, Pitt has offered insight into the breakdown of the marriage, particularly that it came down to him feeling like he was wasting his life; "sitting on a couch, holding a joint, hiding out." He also said that, "I think that my marriage had something to do with it. Trying to pretend the marriage was something that it wasn't." Then he met Angelina Jolie, who made his life much better again. The end.
2 Thandie Newton
1 Angelina Jolie
The world has been good to Brad Pitt. After all, he landed arguably the most beautiful woman on the planet. Yes, we all know the story here: man falls in love with a woman on set while being married to another woman.
Few Hollywood couples have been as much of a media sensation as these two, officially dubbed as one of Hollywood’s super-couples. The couple has become so mesmerizing to the public that it is considered an obsession. TomKat and Bennifer also fit into this super-couple category. What contributes to the fascination with Brangelina? Perhaps it's Pitt’s budding on-set romance with Jolie while simultaneously being married to another big Hollywood name. Or, perhaps it's the couple’s open activism, or their adoption of a number of children from foreign countries, or the birth of their own children, to name just a few intriguing details. Unfortunately, however, the two are forever plagued by magazines reporting that their marriage is breaking down. The most recent claim, courtesy of Life and Style magazine, is that their marriage is actually over, with the headline: “Jealousy, fights and the ‘other man’—shocking details.” Apparently, Jolie is jealous about Pitt’s co-star, the beautiful Marion Cotillard, and we don’t blame her. Is the famous couple truly doomed? Only time will tell.
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