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.
16. Julia Ormond
1994 was certainly a very good year to Brad Pitt in terms of women. He dated Julia Ormond, his love interest in the movie Legends of the Fall, and then moved onto Thandie Newton. Years later, Ormond spoke about the topic of Pitt and Legends of the Fall, commenting on the fact that at the time that they were branding him to be a heartthrob. She said, “It was fascinating to me how, at heart, he’s a character actor, who’s very resistant to that [shirtless] stuff, but at the same time, [understood] that that’s what they wanted from him, or that that was what was required.” In any case, this is just another one of Pitt’s many rumored relationships.
Brad Pitt broke free from only dating the actress-type to take a British pop-singer for a spin in the 80s. The relationship was a relatively high-profile one. Sinitta was actually found by Simon Cowell (and also dated him). The relationship between Pitt and Sinitta may have lasted for as much as two years or so. She was much more famous than Pitt at the time, but her fame has appeared to wane quite a bit since then with her latest stint, lately being a mere mentor on The X Factor. Sinitta has recently talked about her relationship with the heartthrob, saying that, “He was beautiful with the most beautiful body” and that, “He was fun, he was young and very sweet.” We can’t say we disagree with that statement.
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.
Lewis has spoken out about her relationship with the famous heartthrob and is amazed by the fact that people are so interested in the idea that they dated. She said, “All these years later, there’s nothing I can say or divulge about Brad Pitt that would be remotely interesting to any intelligent being.” She went on to say, “’I was a teenager at the time. It’s a lifetime away. I was in my high-school years and it was a wonderful, loving relationship with a fun, smart guy. Then it was over and he went on to become incredibly famous.”
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.
It was 1991’s Thelma and Louise that shot Pitt into international fame and established him as a sex symbol in what became a very famous scene in a very classic American movie. At some point during casting, Davis chimed in with “the blonde one!” when a conversation between directors came up about who to cast for the role. He even beat out Mr. George Clooney himself. Another fun fact? Pitt only earned a measly $6,000 for the role.
12. Jill Schoelen
Jill Schoelen: believe it or not, but she was the very first girl to get a ring from the now famous Hollywood heartthrob Brad Pitt, although the relationship fizzled out quite quickly after just three short months (but still, having the ability to claim this fact is pretty awesome for Jill, we could only assume). The two starred in 1989’s Cutting Class together, which was Brad Pitt’s first movie, and Schoelen hasn’t done much since. However, she does have “engaged to Brad Pitt” on her Wikipedia page, so that’s something, right? Interestingly, however, she was the one who left Pitt for another man. A director, to be exact.
11. Elizabeth Daily/E.G. Daily
Well, there is not very much to say with regards to this entry, other than, Brad Pitt and Tommy Pickles? Yes, that’s right. We assure you, you did read that correctly. Brad Pitt was rumoured to have dated the pop singer E.G. Daily, also known (and probably better known) as Elizabeth Daily, who is widely known as the voice of Rugrats character, Tommy Pickles. So, a woman was actually behind Tommy Pickles’ iconic voice? Yes, that’s correct. This all went down in the year 1989, after one of his many breakups around the same time. Other than what information we’ve provided here, we don’t know much else about this rather questionable relationship.
10. Christina Applegate
Brad Pitt wasn’t the “Brad Pitt” we have come to know and love when he started dating beautiful actress Christina Applegate, in 1989, who was a much bigger star at the time, playing the hot rebel daughter Kelly Bundy, on the TV show Married with Children. In fact, when she took Pitt as her date to the MTV Movie Awards, no one even knew who he was. It didn’t end well, either, as Applegate ended up leaving the MTV Movie Awards with another man. Ouch! Years later, however, Applegate spoke about the topic, saying that she regretted that particular decision. We would probably regret that decision too, Christina. What were you thinking?
9. Claire Forlani
Brad Pitt was rumored to have dated Claire Forlani, his co-star on the fantasy/drama movie Meet Joe Black in 1998. It was a relationship that seems more probable than not, given that the two were seen holding hands at the premiere of the film (then again, could it have been all a show for the film’s promotion?). It is also possible that the two might have dated for as much as an entire year. It was also reported that Jennifer Aniston was his rebound relationship after his breakup with Forlani. What?! Without either party speaking openly of the subject, nothing much is known about their relationship.
8. Shalane McCall
Oh, Brad Pitt. What were you thinking dating a 15-year-old-girl while you were nearly ten years her senior? It appears that he didn’t learn his lesson, either, since he went on to date another high schooler just a few years later (the previously mentioned Juliette Lewis). Brad Pitt met Shalane McCall on the set of Dallas, back in 1987. She was his first on-screen kiss. The rumored relationship was short-lived and not too many details are known about their time together. They do, however, have a set of professional photographs of them available on the Internet, featuring high-waisted blue jeans, 80s style muscle shirts and all. McCall has not acted since 1988.
7. Robin Givens
What do we have here? Another co-star, of course (who was technically still married at the time). Robin Givens, known as Darlene Merriman from Head of Class, was one of several women who Pitt quickly flipped through, kind of like a terrible magazine in a doctor’s office, back in the late 80s. This relationship lasted for about a year, although the dates are murky. And perhaps we can’t be surprised at the short timeline because she was still married at the time to none other than Mike Tyson. Mike Tyson himself has actually spoken about his ex-wife’s relationship with Pitt, saying: “During our divorce, we were f*cking. And one day, I’m going to her house to bone her again and no one’s home, and I’m leaving and she’s pulling up with Brad Pitt, and I’m sad because I’m not going to get any more *****” (you get the idea). Tyson went on to say: “He wasn’t Brad Pitt back then. He was just some little beach-bum-looking dude. ‘Hey dude’ kind of guy. He was probably selling his body for money or something, I don’t know. He was very pretty.”
6. Gwyneth Paltrow
The set of the film Seven was where Brad Pitt originally met actress Gwyneth Paltrow, who was 22 years old at the time, while Pitt would have been 10 years her senior (yes, once again). The two had a very high-profile relationship for their three years together, starting in 1994, which also included an engagement. Paltrow recently opened up about the very public relationship on The Howard Stern Show, saying: “I definitely fell in love with him. He was so gorgeous and sweet.” So, what went wrong? Well, according to Paltrow, she was just too young. She said: “I wasn’t ready, and he was too good for me.” The two remain friendly today.
5. Katja von Garnier
After his high-profile relationship with Gwyneth Paltrow ended up falling apart after three years together, Pitt went on to briefly date (or, at least, was rumoured to have been with) the German director Katja von Garnier, in 1997. von Garnier and Pitt’s names then came up again more than 10 years later when it was reported that they were chatting it up at the premiere of Inglourious Basterds in 2009. As expected, headlines went wild suggesting that Pitt might be having an affair behind Angelina Jolie‘s back and that it was tearing the two apart. Brangelina was still very much intact though, so there probably wasn’t much truth to that story. What a shocker…
4. Demi Moore
That’s right, the Hollywood heartthrob hasn’t ceased to amaze us, as Brad Pitt reportedly also had a thing with none other than Demi Moore, back sometime in the late 90s. The relationship was largely a rumor and was never confirmed by either party. Nothing much more to report on this one – it was widely regarded as a mere fling, otherwise code for the fact that they probably just hooked up a few times. Moore has been linked to just about every actor under the sun, from Ashton Kutcher to Bruce Willis to Ryan Reynolds, so the fact that she was also linked to Pitt isn’t much of a stretch of the imagination, and doesn’t really come as a surprise.
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.
Aniston has also talked about the breakdown of the marriage, saying that after Friends finished filming and Pitt began filming Mr. and Mrs. Smith, “[Brad] just wasn’t there for me.” While it was speculated that Pitt had an affair, Aniston claims to have believed Pitt when he told her he wasn’t physically intimate with Jolie while he was still married. Aniston’s best friend, Courteney Cox, also offered her opinion and said, “I don’t think he started an affair physically, but I think he was attracted to her. There was a connection, and he was honest about that with Jen.”
2. Thandie Newton
Thandie Newton, an English actress known for her roles in 2006’s The Pursuit of Happyness, the Mission: Impossible movies and 2004’s The Chronicles of Riddick, reportedly dated Brad Pitt for an entire year after they met on the set of Interview with a Vampire in 2004. As you might have guessed, she was not very well known at the time. The cause of their breakup is still unknown, but things ended amicably enough to the point that they were reportedly still friends at the time of the breakup. This relationship was just another blip on the radar for Brad Pitt. He probably doesn’t even remember her much (he did go through a lot of women, after all).
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.