Brad Pitt’s Dating History is Wilder Than Any Hollywood Script

Fans all have a favorite Brad Pitt moment: With abs in everything from Fight Club to Troy, the actor has no shortage of blockbusters and cult classics. He was also one of Hollywood’s most eligible bachelors and favorite husband — two times! Brad is single yet again, but how did it all go down?

Hello, Lover Boy

The complete list of every woman that has fallen under Brad Pitt’s spell might be impossible to write. But a decent number of love affairs have been in the news! 

Instagram / @bradpittofflcial

This star has incredibly varied taste — and he even enjoyed being married, when it worked! According to Brad: ”Being married means I can break wind and eat ice cream in bed.” Who temporarily stole this handsome, silly man’s heart over the years, and why did these relationships end?

Next: Take a deep dive into Brad Pitt’s secret dating history, for good and for bad!

Fling: Sinitta Malone

The eighties may seem like ancient history now, but this was the beginning of Brad’s heartbreaker hobby. One of the women that supported him back then was Sinitta, from Toy Boy. The pair dated on and off from 1986 to 1988. And although they didn’t last, they certainly had fun together! 

On a reality show appearance, Sinitta revealed a bit about their time as an item. She explained: “He was beautiful with the most amazing body. I saw him for two years. He was fun, he was young and very sweet.” But Brad was just getting started with the ladies. Who was next?

Fling: Robin Givens

Rumors flew throughout 1986 and 1987 about Robin Givens and Brad Pitt. Overlapping with Sinitta, it seems the aspiring actor couldn’t choose one over the other. Naughty Brad wanted to have his cake and eat it too! But what about Robin’s situation, during this period?

As it turns out, she was still married to heavyweight champion Mike Tyson. Most men wouldn’t dream of getting involved with that love triangle. Yet somehow, Brad seems to have gotten the admiration of the boxer to this day! That Pitt charm must have worked on Mike. Who else got a dose, in the 80s?

Relationship: Shalane McCall

In 1987, Brad went for a blonde. His next love interest was Shalane McCall, an actress many might remember from the show Dallas. They met when Brad played her boyfriend on four episodes between 1987 and 1988. And it looks like she was able to transition to the real thing, pretty easily!

Oddly enough, she was only 15 and he was 21 at the time their dates were rumored. No one would tolerate that, these days! Either way, they didn’t last as a couple. When she was only 17, she married Trend Valladares, her husband today. Who did Brad actually end the decade with?

Fling: Christina Applegate

Brad was not yet mainstream, but he was starting to date some big names in the business. In 1989, he spent time with Christina Applegate. Famous for Don’t Tell Mum the Babysitter’s Deadshe took Brad as her date to the MTV awards that year. It was a great choice, fans agreed!

But Christina wasn’t in a mature dating mode back then. According to the actress: ”I got off on the fact that a guy would be so into me from the get-go without really knowing me. That’s probably why I had so many bad relationships.” Indeed, this one went nowhere. Who did Brad move on to, right away?

Engagement: Jill Schoelen

Though he clearly liked to play around, Brad could appreciate a good connection. His first serious love interest was actress Jill Schoelen. They met on set of the horror movie Cutting Class in 1989, and their chemistry was instant. Brad decided this was worth a ring, and he proposed! 

Jill was his fiance for around three months. And then. the unexpected happened: She ditched him for the director of another movie! It’s tough to imagine Brad getting burned by any woman. But even Hollywood hunks have their ups and downs! How did he move on, to start the 90s right?

Relationship: E.G. Daily

Brad’s next love interest was actually E.G. Daily, the pop star with a voiceover career. She played Tommy Pickles in Rugrats, the pig inthe Babe sequeland a few other well-known characters. But how many people really know she dated Brad Pitt, back in the day?

They tried for a while in 1989, and she has since described him as a laid back and down to earth person. She explained: “He’s the kind of guy that would pick up and leave and drive his car just to get out of the city.” It seems that he still is! But E.G. didn’t last as his girl. Who was next on the journey? 

Relationship: Juliette Lewis

Brad was in the mood for a little art house excitement. He got together with Juliette Lewis, an important name in 90s indie films. Brad was intrigued enough to ask to be her boyfriend — starting when he was 27 and she was just 17! It didn’t last, of course. 

Looking back, Jules reflected: “It amazes me that people are still fascinated that we went out for four years. 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.” He certainly did!

Fling: Geena Davis

Moving on, Brad allegedly dated a costar. With a career on the rise, every A-list woman was interested: It wasn’t confirmed, but it certainly seemed like something was happening with Geena Davis. Working side by side in Thelma & Louise, it was reported they also met up secretly in real life! 

This occurred in 1992, which means another overlap in the love life of the naughty actor. Brad’s then-roommate, Jason Priestly, gave magazines the scoop. Who would know better about covert meetings? This would not be the only costar Brad would romance in the coming years, either. Next was a real beauty!

Relationship: Thandie Newton

Thandie Newton is yet another example of dating at work for Brad Pitt. How could he resist, though? The pair met while filming Interview with a Vampire and dated for around a year afterward. The press certinaly took interest in this affair. Were they public about their relationship?

When asked about it, Brad responded: “Hey, its the 90’s man, leave us alone.” Seems he was getting a bit sick of the press by then! Little is known about their private time, but the relationship came to an end on good terms. They remain friends until today! Brad was in the mood for a model, next. Who did he seduce?

Fling: Jitka Pohlodek

Her name might be hard to say, but it was worth the effort for Brad Pitt. The Czech model Jitka Pohlodek had a short fling with Brad Pitt in 1994. He took her as his date to the premiere of the film Legends of the Fall that year and they certainly looked happy. Were they?

Apparently, Brad was still thinking about an old flame. They were still dating when he revealed his feelings in an interview: He was still in love with Juliette Lewis! Needless to say, Jitka wasn’t impressed with this statement. It ended, probably for the best. But soon, Brad would find another big love. Who was next in his life?

Engagement: Gwyneth Paltrow

Fans are all aware of this relationship, if not many others. It was on the set of Se7en that Brad fell for Gwyneth Paltrow in 1995. And the world went wild! For a time, these two were the number one couple of the mid-90s. At an awards show, Brad thanked Gwen as the “angel, the love of my life”. 

Naturally, he proposed in 1996. But sadly, they called it off seven months later! Like most of his exes, Gwen had a very favorable view of him when it was all over. She later explained: “I definitely fell in love with him. He was so gorgeous and sweet. I mean, he was Brad Pitt!”

Fling: Claire Forlani

After his relationship with Gwyneth Paltrow ended, Brad is said to have briefly dated yet another co-star. This time, it was Claire Forlani, an English actress. Fans might remember her for her role in Mallrats and Police Academy 7: Mission to Moscow. Claire was the face of L’Oréal in 2001 and made the list for Stuff magazine’s “100 Sexiest Women” that year!

Costarring in Meet Joe Black, Claire and Brad got pretty close. They attended the 50th Annual WGA Awards together, making it public. But it was temporary, like most of his affairs. Deep down, this ladies man really wanted to commit. Soon, of course, he would!

Marriage: Jennifer Aniston

True love for Brad Pitt happened when he met Jennifer Aniston. Who wouldn’t fall for the Friends star, back then? Brad certainly was not immune from her charms! They officially met when their agents set them up on a date. That date turned into two years before getting engaged and tying the knot in 2001!

Why did things go so smoothly? According to Jen: “We both [knew] on our first date. It was weird…That was a really easy evening. It was really fun.” It must have been, to pin down this bachelor!

Smooth Sailing

Jennifer was clearly very much in love with her husband. She explained: “He’s certainly a big love in my life…And I know that we have something special, especially in all this chaos. In this nutty, brilliant, wonderful, hard business that we have, it’s nice to have somebody who’s anchored and knows you, really knows all of you.”


But behind the scenes, Brad was having some doubts about this union. Although they were regularly featured in tabloids smiling at glam events, there was more going on in his heart. What was the problem, exactly?

Rocky Roads

According to the actor: “It became very clear to me that I was intent on trying to find a movie about an interesting life, but I wasn’t living an interesting life myself…I think that my marriage had something to do with it, trying to pretend the marriage was something that it wasn’t.”


Apparently, there was a bit of acting going on from this award-winning actor, for the world to see. Brad couldn’t hide his feelings forever, though. Despite the fairytale Jennifer was experiencing, there would soon be a very rude awakening. Sadly so!

An Amicable Split

Divorce was announced to the shock of the world. No one saw it coming! But it seems that these two really were kind to each other, even when tested. According to Jen: “I love Brad. I really love him. I will love him for the rest of my life. He’s a fantastic man…I really do hope that someday we can be friends again.”


The truth is, Brad may have started to look at someone else during this confusing period. On the set of Mr & Mrs Smith, he met Angelina Jolie!

Marriage: Angelina Jolie

Angelina Jolie would be a hard costar to resist, for the most steely of wills. While Brad claims nothing happened between them during the filming, he did admit to falling in love with her! Brad slowly became more involved in his life as she started adopting children from abroad. Then, they had a few of their own!

Dubbed ‘Brangelina’ by the press, this family grew to six before mom and dad finally tied the knot in 2014. Their kids were a part of the ceremony, and fans rejoiced along with them!

Family Man, At Last

Angelina had nothing but praise for Brad, back then. She explained: “It’s such a beautiful and sexy quality in a man when he takes his responsibilities as a father very seriously. I still get very emotional when I watch Brad play with the children—he is so naturally devoted and joyful around them.” 


Growing up in front of the world must have been difficult for Maddox Chivan, Pax Thien, Zahara Marley, Shiloh Nouvel, and twins Knox Léon and Vivienne Marcheline Jolie-Pitt. But mom and dad did their best to shield them from the press!

Finding Passion Again

Brad seemed happy to be a husband and dad, finally. After so many relationships, he had found the one! According to Angelina: “I am very lucky with Brad. He is a real gentleman, but he is also a real man’s man…He’s got the wonderful balance of being an extraordinary, great, loving father, a very, very intelligent man and physically he’s a real man.”


With all the gushing praise from Angie publicly, fans would be shocked just two years into the legal marriage. Something big was about to change their lives forever!

A Shocking Split

Changes were inevitable, for this big brood. Although it had been a pleasant project for a while, the trials of marriage were too much for Brad and Angie. Brangelina was no more, announcing a divorce out of the blue. It was alleged that Brad had a drinking problem, and conflict brought social services into the house!


As it turns out, there had been a lot of fighting going on in the Pitt-Jolie mansion for some time. And there was one more reason that good vibes had gone to bad. What rumors contributed to the tension? 

Fling: Marion Cotillard

Although it’s hard to believe, Claims surfaced that Brad had cheated on Angelina with a costar in Allied. French actress Marion Cotillard denied it, but perhaps some damage was done in the process! With life going from heaven to hell, it was time for some real changes in Brad Pitt’s life.

Perhaps chaos led the actor to seek help. In an interview with GQ, Brad revealed how he was dealing with the divorce: “You know, I just started therapy. I love it, I love it. I went through two therapists to get to the right one.” Fans certainly wish single Brad all the best!

Fling: Nicole Poturalski

Tragic as the breakup of a family may be, it seems he’s doing alright as single Brad. Recently, a new relationship popped up in the news. A 27-year-old German model has been by his side lately: Nicole Poturalski, who is in an open marriage! 

Instagram / @nico.potur

Spotted at events and on vacation together, it does seem they are an item. But both are pretty low key about it all! On Instagram, where she has more than 200,000 followers, she sticks to glam shots. It’s her specialty, after all! Curious observers of Brad Pitt’s dating life notice no pictures of private time with the actor on the account. Not yet, anyway — but only time will tell!

The Wild Dating Life of Leonardo DiCaprio

Leonardo DiCaprio is one talented individual who has had one of the most successful acting careers since way back in 1990.

He has a long list of Award-winning movies on his resume and an even longer list of Victoria Secret model girlfriends. With his Gatsby charm and Romeo romance, there’s no wonder his dating history is richer than anyone in the business! 

Let’s take a look at all the girls that have been in Leo’s life.

Bridget Hall

The first on the list is Bridget Gall. These two were linked in 1994 and she was the first Victoria Secret model he would date but by no means the last.

The two were young, beautiful, and famous and were spotted out and about several times in New York strolling hand in hand.

Brittany Daniel

In 1994 Leo also got cozy with Brittany Daniel, his co-star in his breakout film “The Basketball Diaries.

Though it would not last very long, it was short, sweet and passionate and not surprising considering the very steamy scenes between the two on-screen.

Naomi Campbell

Knowing Leo’s affinity to models it comes as no surprise that he was linked to supermodel and arguably the most beautiful woman on the planet, Naomi Campbell mid-nineties.

The pair enjoyed a brief fling and were the talk of the town when they were together. It soon fizzled out but the two remain good friends until today.

Claire Danes

Although their relationship was never confirmed, rumors were everywhere about the relationship between actors Leo and Claire Danes in 1995.

They starred as star-crossed lovers in Baz Luhrmann’s Romeo + Juliet and it seems their chemistry was so strong it spilled from the screen to real life!

Kirsten Zang

Another model on the list is Kirsten Zang. These two dated on and off for up to a year in 1996 and he brought her as his date to the Romeo+Juliet premier.

One thing you can say about Leo is that he always seems to end on good terms with his long list of lovers. 

Zang, who now owns a gourmet dog food business is still very fond of DiCaprio and often posts throwbacks on her business Instagram account.

Helena Christensen

1997, another year, another love interest for young Leo. This time he was reportedly linked with Helena Christensen.

The Danish model was one of the first women who got Leo’s attention after his meteoric rise to fame that came with his role in Titanic.

Demi Moore

Surprised? So are we! But somewhere between Demi Moore’s separation from Bruce Willis and Leo’s relationship with Gisele, there was a very short time when these two were a thing!

Another rumor that was never confirmed, but with two names as big as there’s, once they were spotted together once, the rumors hit the roof.

Bijou Philips

Another talented individual on Leo’s list of lovers is Bijou Philips- actress, model, singer, and socialite. They dated in 1998 for a short period.

It may have been short, but it worked the paparazzi into a frenzy as they tried to get candid pictures of the young lovers out and about.

Amber Valletta

Another well-known face to add to the long list is Amber Valletta who is…you guessed it, a successful model!

They dated in the late-nineties for a short while. Amber has since moved on and has been married since 2003 to Christian McCaw.

Eva Herzigova

1998 was one busy year for Leonardo DiCaprio. It seems his post-Titanic fame upped his profile and upped his dating game!

He dated another high profiled model, Eva Herzigova for all of a month during that year.

Paris Hilton

Among the most famous and well known on Leo’s dating list is socialite and reality TV star, Paris Hilton!

The two were reportedly together very briefly in the year 200. When these two dated, she was not nearly as well known as she is today and was considered just another one of his flings!

Gisele Bundchen

Arguably his most serious of relationships was with one of the most famous models in the world, Gisele Bundchen.

Leo and Bundchen were together for five years on and off, from 2000 till 2005. 

It was his first long-term relationship and had the world rooting for them to be together forever. we know that didn’t work out but at least they had a few happy years!

Bar Refaeli

Bar Refaeli was also one of the most significant women in Leo’s life. they met at a party in Las Vegas in 2005 and were on and off for years.

There were many who thought it would be this Israeli model who would get Leo to settle down. Alas, they ultimately broke up in 2010 and she has gone on to get married and have a child with an Israeli businessman.

Blake Lively

It seems you cannot be a Hollywood IT girl without at least having a short romance with Leo. He was rumored to have wined and dined Blake Lively for a short while in 2011.

Although she called him a friend, there was no denying the spark between them as they were pictured side by side in New York and Paris. 

As we know, she has since moved on and is now happily married to Ryan Reynolds with two children.

Alyce Crawford

Rumor had it that just days after his split from Blake Lively, he was cozying up to Australian model Alyce Crawford.

It was during his filming of The Great Gatsby which was shot in Australia that he is said to have had regular visits from the 21-year-old former Australian Next Top Model Contestant at his hotel!

Madalina Ghenea

It seems Leo wasn’t lonely for a second when he was stuck in Australia filming The Great Gatsby. Another fling during the time was Romanian model Madalina Ghenea.

While the flame fizzled out after only a few dates, he reportedly spent his birthday with her, which is a pretty big deal.

Erin Heatherton

Another one of Leo’s longer relationships was with yet another Victoria Secret model, Erin Heatherton/ they dated for all of a year from 2011 to 2012.

Although they didn’t last, she remains fond of her ex stating in 2015. “He’s a wonderful person and he’s a friend of mine, I wish him all the best.”

Miranda Kerr

She has a history with a handful of uber-famous men, including Orlando Bloom who she was married to and has one child with. However, in 2013 the rumors swirled when Kerr and Leo were spotted on a date.

However, nothing seemed to come of it. She is one of the only brunettes in Leo’s dating pool and is now married to the CEO of Snapchat, Evan Spiegel.

Kat Torres

Kat Torres herself confirmed that she was in a relationship with Leo in 2013. The Brazilian model and influencer met the actor at the Cannes film festival were sparks flew.

Kat is the exact type Leo goes for usually, blonde, a model, and a few decades younger than he is!

Toni Garrn

In terms of dating Leonardo DiCaprio, a year is one hell of a long relationship that only a few women got to have. Among them is German model Toni Garrn.

Toni and Leo dated from May 2013 to December 2014 and were seen together all over the world during their relationship. She was only 21 when they started dating.

Kelly Rohrbach

His most recent ‘long-term’ relationship was with model Kelly Rohrbach who he dated for around a year from 2015 to 2016.

While they were dating, rumors swirled of an engagement and for a moment it was believed that the worlds eternal bachelor was no more! But alas, they split in 2016 putting those rumors to bed.


They are both not each other’s usual type, yet there were rumors in 2015 that Leo and Rihanna were seeing each other, and pictures to prove it!

The headlines were everywhere, but they were also short-lived and quickly disappeared. Though let’s be honest, they would make quite the power couple.

Nina Agdal

Danish model Nina Agdal was linked to Leo in May 2016 when they were spotted out and about in New York multiple times.

Agdal, who is a Sports Illustrated model and Maxim magazine cover girl, not to mention a Victoria Secret model (obviously) denied that they were ever together. 

But the pictures are louder than her words!

Laura Whitmore

Also, in 2016 was Leo’s brief fling with Irish presenter Laura Whitmore. The two met at a party and Leo was smitten.

As a tall, blonde, young famous woman she fit Leo’s type perfectly. They had a quick fling before it was over.

Lorena Rae

The year 2017 didn’t see any slowing down in Leonardo DiCaprio’s dating habits. 

Just three months after ending with Nina Agdal, he was spotted with German model Lorena Rae.

The two were spotted having a lunch date on park avenue and riding CitiBikes together, which is known to be a Leo favorite activity to do with girlfriends.

Juliette Perkins

Another month, another rumored girlfriend for Leo. This time it was Kiwi model Juliette Perkins who was rumored to be romantically linked to the eternal bachelor.

The actor was seen leaving a club with the then 19-year-old Perkins (that’s a 23-year age gap if you can’t do the maths) Considering Leo has basically been with every model under the sun, this came as no surprise.

Camila Morrone

Since late 2017, the model that took center stage in Leo’s love life has been Camilla Morrone. 

The brunette has been with Leo for over a year, which is a pretty big deal, and the two tend to keep a low profile while out and about.

Could the 21-year-old model be the one who finally captures Leo’s heart forever and gets him to settle down? We doubt it, but at least they’re happy for now!