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Brad Pitt's Most Notable Exes + A Few Ladies Who Flew Under The Radar (20 Pics)

Many people have joked before about the fact that Brad Pitt seems to change his personality and overall look based on who he's dating. To some extent, we all make compromises when it comes to our relationships.

However, looking at photos of him with any of his past girlfriends, we can kind of see what the general public is talking about! He definitely tweaks his overall look a bit based on the woman he's with.

And, as Pitt has been in the industry for decades now, he has quite a few relationships under his belt—although there are many that even fans don't know about. Sure, most people know about his marriages and his more recent relationships. However, do they know who Pitt dated back when he was just a young rising actor trying to make a name for himself in the industry? He was linked to quite a few women in the '80s and '90s, and many of them are names fans may not even know.

Whether Pitt confirms another relationship soon or remains a bachelor for years to come, we can't wait to get even more details on his love life. We just can't help ourselves! Here are his most notable exes (and a few lucky ladies who flew under the radar).

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20 Notable: Rockstar And Actress Juliette Lewis

via: huffingtonpost.com

Most people know who Juliette Lewis is. She got her start in the industry when she was just a teenager and has moved between acting and being a total rock star over the years. We would not in a million years have imagined her as one of Brad Pitt's exes, though. She just seems way too wild for him! However, Lewis acknowledges that it was kind of just teenage love.

As she spilled to Daily Mail of their four-year relationship, "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."

19 Notable: Christina Applegate, Who Ditched Him For Another Guy

via: loudersound.com

Many women would give just about anything to go on a date with Brad Pitt. That's true today, and it was especially true back when he was a 20-something heartthrob. However, Christina Applegate had a bit of a different perspective. The two of them had a bit of a casual relationship in 1989, briefly dating for a while and attended the MTV Movie Awards together.

Part of the way through the awards, though, Applegate ditched Pitt for another guy. Talk about crazy! Obviously, the relationship wasn't meant to be if she couldn't even handle one evening together. Still, what a crazy story Applegate can bust out from time to time.

18 Under The Radar: Teen Actress Shalane McCall

via: popsugar.com

Brad Pitt is often seen as a charming and somewhat wholesome actor. While he's been in the tabloids a fair bit because of his star power, he isn't the type to be constantly surrounded by controversy. That's why many people have forgotten altogether about the buzz about him in 1987. Pitt met young actress Shalane McCall when he did a four-episode stint on Dallas, and sparks flew.

Many people raised their eyebrows at the brief fling, though, since Pitt was 24 and McCall was just 15 at the time. It wasn't exactly a serious relationship though and didn't end up lasting past Pitt's stint on the show.

17 Notable: His Thelma & Louise Co-Star Geena Davis

via: eonline.com

While there are plenty of celebrities who work with other stars and then go back to their regular relationships, it's hard to deny that sparks fly on set from time to time. After all, you're spending a lot of time around the same people—if there's chemistry, you'll notice it!

We're a little bit surprised that sparks flew on the set of Thelma & Louise and Davis and Pitt ended up getting together. They seem like an unlikely pair!  At the time, Davis was the much more famous of the two, and Pitt's former roommate admitted that she made sure all their romantic rendezvous were private, away from the paparazzi's prying eyes.

16 Under The Radar: Sparks Flew Off Set With Co-Star Julia Ormond

via: imdb.com

Okay, we're beginning to think that all Brad Pitt needs to do to start a relationship is appear in a movie with someone. It happens way, way too often! This relationship is no different. Pitt met actress Julia Ormond when they worked together on the movie Legends of the Fall. The two never actually confirmed their relationship, but there was a lot of speculation about the fact that the on-screen romance turned into a real-life romance.

Given Pitt's track record of falling for co-stars, we totally believe it. Seriously, all his single female co-stars should think twice before taking on a Pitt project—they may come out of it with a new boyfriend!

15 Under The Radar: Singing Sensation Sinitta

via: femalefirst.co.uk

In a lot of his relationships, Brad Pitt has been the more famous one. The dynamic in his relationship with British singer Sinitta was a bit different, given the way it started out. Apparently, he saw her performing on TV and fell head over heels in love with the superstar, who is from the UK.

Brad apparently begged his agent to call Sinitta's agent and try to make something happen, and the agent must have set up a date because they ended up becoming a couple. Sinitta has nothing but good things to say about her ex, telling Marie Claire that "I saw him for two years. He was fun, he was young and very sweet."

14 Notable: Vampiric Co-Star Thandie Newton

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There are so, so many celebrities we never would have put together, and Brad Pitt and Thandie Newton are two of them. However, the two ended up dating for a short period of time back in the '90s. How did they meet? How else—on set. Pitt clearly doesn't need to worry about where he'll meet his next partner—it always seems to be on set!

The two worked together on Interview with the Vampire and dated for a while before parting ways. They parted on good terms, though, and stayed friends over the years. We imagine a bad breakup would make things awkward on the red carpet!

13 Notable: Consciously Coupled With Goop Queen Gwyneth Paltrow

via: vanityfair.com

Brad Pitt met actress Gwyneth Paltrow on the set of the movie Se7en, and the two totally hit it off. They started dating in 1994 and were together for about three years. They were both big stars, and their relationship was super, super public. In fact, Pitt even decided to propose to her on stage at the Golden Globes when accepting his award. They were engaged for about seven months before calling things off.

Paltrow has spoken many times before about the fact that she was simply too young for the relationship, and the timing wasn't right. They were certainly a super chic couple though!

12 Under The Radar: Jill Schoelen, Who He Proposed To

via: pinterest.com

Unlike many other men, Brad Pitt definitely isn't afraid of commitment. He goes after what he wants and isn't shy about taking that next step. Back in 1989, he started dating actress Jill Schoelen after meeting her on the set of the movie Cutting Class. He proposed, and they were engaged for about three months before Schoelen dumped him—she had fallen for a director. Can you imagine being the woman who dumps Brad Pitt?

Schoelen eventually retired from the industry, focusing on being a mom to her two boys instead. Her life would definitely have been totally different if she ended up becoming Mrs. Brad Pitt.

11 Under The Radar Until Confirmed: Gorgeous A-Lister Charlize Theron

via: chatelaine.com

There are always a ton of rumors flying around about who is dating who, especially with high profile celebrities. One innocent lunch date between friends can explode into a perceived relationship. So, when rumors started circulating that Brad Pitt was dating actress Charlize Theron, many people were skeptical. They're both huge stars, surely it's just the tabloids trying to get a little extra attention, right?

Well, we're not entirely sure—if these two end up dating, it'll definitely be a high profile, really public relationship. For now, though, it's all just rumors—but we can't wait to see if they confirm their relationship status!

10 Under The Radar: E.G. Daily, The Voice Behind Your Favorite Cartoons

via: gettyimages.com

You probably wouldn't know who E.G. Daily was if you saw her. However, the moment she opened her mouth, you'd know exactly who she was. The singer and actress has dabbled in different facets of the industry but received the most success as a voice actress behind characters like Tommy Pickles on Rugrats.

There was something about the free-spirited actress that Pitt really liked, and he ended up dating her for a short time after his former fiancee Jill Schoelen broke up with him in 1989. It didn't last for very long, which is why many people didn't even know the two were a thing at one point.

9 Under The Radar: Actress Sonita Henry

via: yahoo.com

Pitt has definitely had a ton of relationships over the course of his years in the industry, with women from all over the world. UK star Sonita Henry was one of the exes who he reportedly dated back in the late '90s. The two kept things pretty quiet, and never actually came out and confirmed that they were seeing one another.

The brief relationship didn't last long, so the tabloids didn't exactly do too much digging. Henry definitely hasn't reached the level of fame that Pitt has, but who knows—perhaps her time to shine and thrive is coming up soon!

8 Under The Radar: Mike Tyson's Ex, Robin Givens

via: huffingtonpost.com

Dating someone with a notable ex is hard enough—you don't want the tabloids to start proclaiming you the rebound, after all. However, things are even more complicated when your ex is a world famous boxer. Pitt got wrapped up in a bit of a tricky situation back in 1989 when he started dating actress Robin Givens. He snagged a spot on her sitcom, Head of the Class, which was one of his first ever acting roles.

Sparks flew between the two of them, but Robin's estranged hubby Mike Tyson wasn't having it. He apparently threatened Pitt after finding the two of them together, which would cool down even the most fiery relationship.

7 Under The Radar: Boho Queen Sienna Miller

via: celebmafia.com

Brad Pitt went through a phase when he definitely had a bit of a boho vibe. He favored more casual clothing, his facial hair was a little scraggly, and he rocked longer locks. It comes as no surprise that he was linked with the boho queen herself, Sienna Miller, during that time.

A source spilled to Us Weekly that Pitt and Miller were spending time together and the two were spotted at Glastonbury Festival together. However, neither ever confirmed the relationship, so it obviously didn't get too serious. Sometimes, the timing just isn't right, or something doesn't work out in the long run.

6 High Profile: His Infamous Second Wife, Angelina Jolie

via: stylecaster.com

Pitt's relationship with actress Angelina Jolie is definitely his most notable relationship of all time. After all, at the time it happened, people around the world were in total shock. He and former wife Jennifer Aniston were Hollywood's golden couple, so the fact that they split up was surprising enough. The fact that he immediately moved on to a few relationship with someone totally different had fans reeling!

The two got together in 2005 and soon had a baby on the way. They were together for nearly a decade, and share six children—some adopted, some biological. They definitely had a complex relationship, and things just went south in the end. Love isn't easy, not even in Hollywood!

5 Under The Radar: Stunning Model Jitka Pohlodek

via: eonline.com

We have to be honest, we're a little bit surprised that Pitt hasn't dated way more models over the years. After all, he's Brad Pitt! If Leonardo DiCaprio can have a new supermodel on his arm every week, surely Pitt can as well? However, it seems that Pitt prefers actresses to models—although he did make an exception for model Jitka Pohlodek.

The two dated briefly in the mid-'90s, and Pitt took her as his date to the premiere of his movie Legends of the Fall. However, it never really seemed like a serious thing—in fact, they were supposedly together at the same time Pitt spilled to Vanity Fair that he loved his ex, Juliette Lewis.

4 Under The Radar: On-Screen Romance Turned Off-Screen Fling With Claire Forlani

via: popsugar.com

Okay, honestly—it would be easier to list the former co-stars Brad Pitt hasn't had relationships with than the ones he has! Actress Claire Forlani starred opposite Pitt in the movie Meet Joe Black, and apparently, they were drawn to one another off-screen as well. They reportedly had a brief relationship, although it didn't last beyond a few dates.

It just goes to show how tricky relationships that start on set can be. Sometimes, there can be chemistry when you're spending so much time together, playing characters who love one another, but those feelings just can't hold up in the real world.

3 Under The Radar: Rumored Romance With Actress Demi Moore

via: standard.co.uk

Demi Moore has had her fair share of high profile romances. First, to actor Bruce Willis, who she was married to for quite some time and had children with. Then, to the much younger Ashton Kutcher. However, many people don't know that Moore was actually linked to Brad Pitt for a while back in the '90s.

The two supposedly dated for a short period back in 1998, although obviously, things didn't end up getting serious. It just goes to show how small a world Hollywood truly is. There are so, so many actors and actresses who end up dating that we never would have even guessed.

2 High Profile: Hollywood's Favorite, Jennifer Aniston

via: newidea.com.au

Jennifer Aniston is definitely one of Brad Pitt's most high profile relationships. After all, they were married! They were together during a time when they were both at their peak level of fame and were basically Hollywood's golden couple. In fact, it's a little tough to believe that they were only married for about five years—it seems like much longer!

Regardless, after a blind date set up by their agents, they dated, they married at a luxe Malibu wedding, they walked countless red carpets together and were totally in love. They split after Pitt starred in Mr. and Mrs. Smith with a certain other actress and have pretty much avoided one another ever since.

1 Under The Radar: Brainy And Beautiful MIT Professor Neri Oxman

via: eonline.com

It's always fascinating when a celebrity ends up dating someone who is a superstar in a different field. For example, people were endlessly obsessed with George Clooney and Amal Alamuddin's relationship. If Pitt ever dated someone outside of Hollywood seriously, people would be just as interested in that relationship. It almost happened when he was rumored to be linked to MIT professor Neri Oxman.

Rumors circulated about the two of them, but they both denied the relationship and things fizzled out. Still, who knows—perhaps Pitt will be linked to another woman outside of Hollywood someday! It would probably be a whole lot easier to handle a relationship where only one person is an A-List superstar chased by the paparazzi.

Sources: Popsugar, Ranker, EOnline, MSN

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