Ben Affleck's Dating History is Wilder Than Any Hollywood Script
In Hollywood, it's easy to get typecasted after a strong first role. But actor Ben Affleck has done quite a bit since his debut in Good Will Hunting. The clean-cut Bostonian hunk quickly upgraded his career, and with that — his love life!
Ben now enjoys a new generation of fans who first saw him in thriller Gone Girl, or capturing villains in Suicide Squad and Justice League. He has collected not one, but two Oscars along the way. And more than a few ladies have noticed!
But did viewers really notice all his romances with famous femmes? And what about his penchant for dating everyday, professional women? In romance, Ben is full of surprises!
Next: Check out Ben's surprisingly diverse dating history — from the early days to today!
Relationship: Cheyenne Rothman
How did Ben meet his first love? Romantically, they actually met at summer camp. After dating on and off through their teen years, into college, and beyond, they took separate paths in 1997. After Ben won his first Oscar, things went south! Who would date next, now a Holywood man?
Relationship: Gwyneth Paltrow
It's not hard to see why Ben fell for Gwyn: The starlet was an absolute it-girl in the 90s, and Ben caught her eye. And she caught his, mutually! Meeting in 1997 at a dinner party, they were both smitten. The chemistry would translate well on screen, too!
In 1998, they worked together on a film exploring the Elizabethan era: Shakespeare in Love. Ben found himself involved in a second film nominated for numerous Oscars. Things were going well, career-wise. But troubles were brewing with his own m'lady. Ben Affleck and Gwyneth Paltrow split, suddenly!
Or Did They?
The tabloids were devastated to lose their favorite story. But soon enough, they got more material: Ben and Gwyneth reunited! Behind the scenes, their relationship was back on. On-screen, they were together again in the movie Bounce. Breakups and shakeups in their relationship continued, however.
In 2000, the young Hollywood couple broke up for good. Gwyneth spoke about a difference in value systems, in interviews. She also shared: "He's super intelligent and really, really talented and he’s funny. But he wasn’t in a good place in his life to have a girlfriend." How does she feel about this vintage romance, reflecting today?
All's Well That Ends Well
In recent years, Gwyneth has searched for perspective on the high profile affair. She now says: "I think there’s certain boyfriends where you are trying to work stuff out, right? Like, you’re trying to heal certain stuff from your childhood and he was very much a lesson in that way."
Fans cheered as Gwyn moved on in a major way with rockstar Chris Martin. But life is a learning curve, and Ben wasn't done with his own research. Who would he date next, in a town with so many gorgeous girls?
Engagement: Jennifer Lopez
It was a bit shocking, at first — but fans were intrigued by the next relationship in Ben Affleck's history. Jennifer Lopez was a superstar in the music industry already. And back then, she was transitioning to an interesting crossover career in film. Romantic comedies really suited her, it turned out!
Ben met Jen on a film set, sparks flew, and the press went wild! And soon, they would act in a film together showing the world their chemistry. What was the name of that infamous project, as a memory refresher?
A Real Razzie
Gigli was a 2003 comedy that got more press than most, but not for the right reasons. Ben and Jennifer co-starred in the film, hoping their relationship would translate on screen. Sadly, The Wall Street Journal called it, “the worst movie — all right, the worst allegedly major movie — of our admittedly young century.” Yikes!
While Ben and J-Lo made around $12 million each for their roles, the movie did not make back its investment. It persisted as an industry joke, for years after its debut. Did this reputation hit affect their romance, behind the scenes?
Popping the Question
Perhaps Gigli can never be quantified, in that way. And a quick glance would reveal things were just fine. In fact, a big move happened not long after the film bombed: Ben proposed to Jennifer on a visit to his mom and dad in Boston. The perfect place to seal the deal, for Boston boy!
Reports say that Jennifer saw a blanket of rose petals throughout the family house, and candles lit everywhere. Ben read a heartfelt letter and presented her with a giant rock. The pink diamond would receive as much publicity as the engagement itself!
A Shocking Reversal
But something was missing, in Jen's world. She had the ring, and she had the A-list man. The world was shocked when it was announced that J-Lo ditched Ben Affleck the day before they were supposed to tie the knot. Ben was probably the most shocked of all!
What happened? The truth may never be fully known. But Jennifer Lopez has since talked about the scandal in interviews. She now reflects: “I felt suffocated miserable and gross. I should never have gone down that route or got sucked into all the publicity.” How did Ben deal with this unexpected twist in his happy ending?
Relationship: Enza Sambataro
Ben Affleck was a single man again, and he decided to go back to his roots. Dating local Boston sales executive Enza Sambataro, the two were frequently spotted at baseball games. But like all his public moves, the pair was followed by paparazzi. Enza did not enjoy this first-class treatment!
Ben reflected: "I feel like I'm this walking nightmare. You get photographed with me once at a baseball game, and The Inquirer will find out every dirty little thing that ever happened in your family's history." Evidently, it was too much for his new gal, and they split after 2 months. Who would be prepared to be a part of his life, for good and for bad?
Marriage: Jennifer Garner
In the end, perhaps Ben needed someone who understood the pros and cons of fame. With Jennifer Garner, he found an exceptional balance: An authentic girl next door from a small town with a deep knowledge of his business. No wonder he pursued the Alias star!
According to Ben: "We met on 'Pearl Harbor,' which people hate, but we fell in love on 'Daredevil.' By the way, she won most of the fights in the movie, which was a pretty good predictor of what would happen down the road." Neither were single on the first set. Ben was still with Jen number one! But two summers later, all bets were off.
The Stars Aligned
Jennifer Garner was actually married to actor Scott Foley, back in the day. Despite rumors that Ben had something to do with their split, Jennifer explained: "We didn't have a shot. He's a really good guy, and we just imploded." Scott emphasized similar notions in his interviews, too. Would Ben be a better match?
In 2004, Jennifer Garner and Ben Affleck started making open appearances as a couple. Seen in public at baseball games and on movie set visits, people noticed how happy they were. No one was surprised when Ben proposed on her 33rd birthday!
Family Man, At Last
After a small private ceremony, their marriage began. Ben and Jen welcomed three kids — Seraphina, Samuel, and Violet. And Ben was happy with his newfound stability! He explained: “She is by leaps and bounds the most important person to me in that respect...Over the past 10 years, she has allowed me to have a stable home life while accomplishing my professional goals.”
It certainly appeared that Ben finally found his storybook ending/ For a time, no one questioned it. But behind the scenes, trouble was secretly brewing. What was the issue in the Affleck-Garner house, outside of the public eye?
Perhaps fans did know what Jennifer did — Ben was dealing with alcohol addiction at home. What's more, rumors of infidelity swirled: Was the actor actually having an affair with the nanny of his three kids? A divorce was finalized after ten years of marriage.
Ben went into treatment, and Jen shared some truth in interviews: “We had been separated for months before I ever heard about the nanny. She had nothing to do with our decision to divorce. She was not a part of the equation.” Ben expresses regret to this day about the dissolution of his family. But he continued looking for love, and a funny woman would cheer him up next. Who, exactly?
Relationship: Lindsay Shookus
Lindsay Shookus may not have been on screen directly, but she was a powerful name behind the camera for a long time. Head of the talent department at SNL and a producer, she was someone Ben respected in the industry. Evidently, he was also interested in her off the clock!
Ben and Lindsay went public with their love in 2017. They moved in together after only a few months of dating! But sometimes things that burn bright, burn out the quickest. The pair split in 2018, and continued living busy lives on different coasts. Who did Ben date next?
Fling: Shauna Sexton
Ben Affleck, now 46, was in the mood for a young Playboy name. For a short period, he was spotted dating Shauna Sexton, 22. Seen all around LA, they made a photogenic pair. Their short affair included a trip to Montana with social media posts by the model. But the truth is, Ben probably wasn't ready for anything serious. He was still dealing with his alcohol addiction!
Ben chose to check into rehab, and received some visits from Shauna during his 40-day stay. But this romance would not last, and both moved on to other people. Who would Ben date immediately afterward?
Lindsay Shookus Again
Why it was none other than Lindsay Shookus! In 2019, they reconciled. At this point, the tabloids were filled with pictures of them enjoying the hotspots of New York, London, and Cali. They laughed at comedy shows together. But would this time turn out better than the last?
No, it was short-lived. Lindsay had an ex and a child on the east coast, and Ben had his on the west coast. They tried to give it a real shot, but it just didn't work in reality. Who would fit better with his lifestyle, next?
Fling: Katie Cherry
Ben's new love interest was now Katie Cherry, an up and coming singer in Los Angeles. Spotted at the UNICEF Masquerade Ball and the Commerce Casino together, fans took notice. But how did they meet? Apparently, it was a match from the dating app Raya. That's Tinder, just for celebrities!
Katie was not a stranger to the trials and tribulations of Los Angeles. She was a friend of party girl Tara Reid and the ex-girlfriend of Mike “The Situation” Sorrentino from Jersey Shore. Nothing ever got serious with Ben, though. Who did he date next?
Relationship: Ana de Armas
Ben was soon spotted in Cuba with a co-star: Model and actress Ana de Armas. The two play husband and wife a psychological thriller called Deep Water. Perhaps working on a freaky film is a bonding experience! After five months of dating, Ana posted pictures of them as a couple on her Instagram account.
She is set to be the latest Bond girl, as well. In the upcoming film No Time To Die, viewers will be able to get to know her dangerous side further. For now, that's a secret reserved for Ben!
Marriage: Jennifer Lopez (this time for real)
After sparking romance speculation in April 2021, Us Magazine confirmed that the former couple had been spending time together again. A source told Us Magazine that the exes have “always loved each other” and Lopez’s friends “won’t be surprised if they end up together.” A second source added that the duo had a “heart-to-heart” following their respective splits from Ana de Armas and Alex Rodriguez in 2021, which “reignited a spark between them.”
The Dramatic Dating Life of Leonardo DiCaprio
Everyone has a favorite Leonardo DiCaprio movie: With iconic roles in everything from Titanic to Django Unchained, the actor has emotional range and depth. Puzzlingly, he remains one of Hollywood's biggest bachelors — with no end in sight!
His Heart Will Go On
Leo is one talented guy, something audiences have recognized since the '90s. At this stage in his life, he has a net worth of $260 million and enjoys regular Oscar nominations. But fans secretly wonder: Who is really on the long list of women that helped him along the way?
It has been said that Leonardo dates Victoria's Secret models, as well as Victoria's Secret models. But does he really restrict his taste to the top talent in the lingerie business? Inquiring minds want to know just whose hearts he's been breaking, for three decades!
Next: Take a tour of Leo's enviable, A-list dating history — from the '90s to modern 2020!
Fling: Bridget Hall
It's no surprise that the first publicly linked woman to Leo was a lingerie professional. The man has a pattern! Young Bridget Hall was making waves as a top Victoria's Secret model when she appeared on the arm of the actor in 1994. But alas, it wasn't meant to be!
Tabloids stopped seeing them stroll NYC hand in hand when she dumped him. Allegedly, Bridget was not impressed with him after spending the night together! But did Leonardo give up on his dream to date runway vixens? Not by a long shot!
Fling: Brittany Daniel
A blast from the past, 90s teens will recall Brittany Daniel from Sweet Valley High and later, The Game. Her TV career was going well enough, but Brit occasionally waded into film. In 1994, she dated her costar in The Basketball Diaries. It was Leo!
With all the awards he has racked up in recent years, it's easy to forget the films that started his career. Fans might actually remember the steamy scenes in this one! It's no surprise they tried it out in real life. But Leonardo really wanted something else. Who, or what?
Fling: Naomi Campbell
According to supermodel Naomi Campbell: ''I don't always wear underwear. When I'm in the heat, especially, I can't wear it. Like, if I'm wearing a flower dress, why do I have to wear underwear?'' A good question. Leo, of course, had the answer!
The actor's true appreciation of models led him to this 90s phenomenon, but it only lasted for a short while. Naomi herself has a history of short term relationships. Today, they are still friends. No hard feeling for the fling! Who would be next, in Leo's love life?
Fling: Claire Danes
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!
But was Claire actually as romantic as her character? It seems she didn't believe that people were meant to be together. According to the actress: ''You have to have a lot in common, choose well and be really fortunate. It's not like you're sprinkled with fairy dust. You have to believe that love will be there when you need it.'' In this case, it wasn't. Leo had other plans!
Relationship: Kirsten Zang
Model time, yet again. This was actually a relationship, for around two years! Kirsten Zang was Leo's love for a bit, and she even attended the premiere of Romeo + Juliet. Between 1996-1998, people thought Leo might have found the love of his life!
This blonde bombshell wouldn't be his last, though. Although the pair broke up, they remain on good terms today. Kirsten runs a gourmet dog food business now, and sometimes gives him a shoutout on her business Instagram account! Which brunette model was Leo in the mood for, next?
Fling: Helena Christensen
Leo was interested in moving up from models. It was the era of supermodels, and he set his sights on Helena Christensen. The Danish Victoria's Secret Angel once explained: ''I was born in high heels and I've worn them ever since.'' Perhaps that is what got his attention?
Whatever the case may be, this arrangement was short-lived. Leo was a hot commodity during this period, having recently starred in Titanic. Perhaps he just wasn't ready to settle down as his career went up, up, up! Who was next on his lover list?
Fling: Demi Moore
It may be a bit surprising, but Leo and Demi Moore were rumored to have had a short romance in the late '90s. Sometime after her famous separation from Bruce Willis, G.I. Jane dated the younger actor. And as fans know, this wouldn't be her last time!
It was never officially confirmed, but the gossip wouldn't go away. Based on Demi's real marriage to Ashton Kutcher just a few years later, it's not hard to believe! Who did Leonardo Dicaprio pursue after checking this 80's fantasy off his bucket list?
Fling: Bijou Philips
In 1998, Leo met Bijou Philips. The actress, model, and singer became known as a hot socialite, and the tabloids loved her. While they ultimately broke up, this dating episode may have helped her career. Many may not know the backstory!
Bijou was already the daughter of singer John Phillips, from The Mamas and the Papas. She was on the cover of Italian Vogue when she only 13. But Leo helped her get the lead role in Black and White in 1999, which led to further gigs. These days, the actress is married to Danny Masterson from That 70's Show. A happy ending, no doubt! Was Leo ready for his own yet?
Fling: Amber Valletta
Another big name model was on Leo's mind, after Bijou. Amber Valletta dated him for a bit in the late 90s. When they met, she had already been the face of Giorgio Armani, Chanel, Louis Vuitton, Prada, and more. Plus, she was known as a host on the MTV show House of Style. No wonder he noticed her!
But like most of Leo's curiosities back then, it didn't go anywhere. Amber moved on and found lasting love and marriage with Christian McCaw, an American Olympic volleyball player. What did Leo decide to do with his own love life in 1998?
Fling: Eva Herzigova
Post-Titanic fame really helped Leo get to the next level in dating value. He caught the eye of supermodel Eva Herzigova, and they hit it off. For how long? Estimates are, about a month!
Born in Czechoslovakia, Eva made it to household name status in countries well beyond Europe. Conquering covers from Japan to Mexico to Turkey, designers couldn't get enough of her. Eva was pretty busy walking the runways for Louis Vuitton and Versace. Is that why things didn't work out with Leo? That remains a mystery, to this day!
Fling: Paris Hilton
According to socialite and reality TV queen Paris Hilton: ''Every woman should have four pets in her life. A mink in her closet, a jaguar in her garage, a tiger in her bed, and a jackass who pays for everything.'' How did Leo fit into this model?
Reportedly, the actor dated Paris for a brief period in the early 2000s. She wasn't as well known back then, but she caught his eye nonetheless! Clearly, this was a fling. Next, though, Leo would finally try out something long term. Who made the cut?
Relationship: Gisele Bundchen
The world went wild when Leo came out as supermodel Gisele Bundchen's real boyfriend. Both at the top of their fields, by then, fans approved of the match. The glam, leggy Brazilian was his first public long term relationship. They dated for 5 years, believe it or not!
From 2000 till 2005, it seemed both had a few happy years. But according to Gisele in recent interviews, she was dealing with anxiety and suicidal thoughts back then! It's incredibly surprising to hear, considering the image created by tabloid photos. What was the issue?
No one knew it at the time, but off the runway, the Victoria's Secret model was suffering from panic attacks. According to Gisele: "I had been smoking cigarettes, drinking a bottle of wine and three mocha Frappucinos every day, and I gave up everything in one day...I thought, if this stuff is in any way the cause of this pain in my life, it's gotta go." But was that the only thing in her life that she needed to change?
At the time, Gisele says she began to feel alone in her relationship with Leonardo. They broke up, to the great shock of the paparazzi! What were her thoughts on dating the Hollywood star, overall?
Reflecting now, Gisele explains: "Everyone who crosses our path is a teacher; they come into our lives to show us something about ourselves...and I think that's what he was. What is good versus bad? I honor him for what he was."
It seems she learned a lot about herself, through the experience. Next, she found real love: Gisele has been married to football star Tom Brady since 2009, and they have built a family. The model is now a mom and a stepmom! Would Leo be ready in his own life, soon?
Relationship: Bar Refaeli
Next, Leo would pursue another real relationship. Flings be gone! Model Bar Refaeli caught his attention at a party in Las Vegas, back in 2005. The Israeli beauty would be known as his girlfriend, on and off for years. There were even rumors about a ring!
Voted No. 1 in 2012 on Maxim magazine's Hot 100 list, many thought this would be the model who would get Leo to truly settle down. But no! The actor became a bachelor yet again in 2010. How did Bar deal with this fact, after such a hyped and public romance?
From Model to Mommy
Actually, quite well! The most successful Israeli model in the biz had no trouble finding a wealthy husband back home, pretty quickly. Bar married businessman Adi Ezra in 2015, and got straight to babymaking!
Fans were delighted to see this gal in love yet again. So far, the couple has two daughters, and a son: Liv, Elle, and David. With baby number three born in 2020, some might think Bar is resting with so many kiddos running around. And they would be wrong! How does Bar contribute to the bills?
Bar Rafaeli is the part-owner of Carolina Lemke Berlin, a glasses and sunglasses boutique. She is trying to expand it internationally, and many may have noticed her company's creative campaigns! Recruiting 'hot felon' Jeremy Meeks to star by her side in a campaign, fans loved the move!
According to the company: “There has never been a mix like this.” Next to one of the most interesting faces in the world, Billboards all over Israel featured the pair. Bar seems pretty busy, all things considered. But whatever happened to Leo, mister single?
Relationship: Blake Lively
Surprisingly, Leo bounced back into another relationship. Perhaps he had gained a taste for it, after spending quality time with Bar. Who knows? Spotted with Blake Lively for five months in 2011, tabloids snapped them having brunch on a regular basis in NYC and Paris.
Leo was even seen with then actress on a yacht during Cannes and on a trip to Disneyland. These were real dates, to be sure! But for whatever reason, the love didn't take. Hollywood It-girl Blake was meant to be with someone else, and fast!
Totally Meant to Be
Within a month of reports that Leo was no more, Blake was spotted with someone else: Funnyman Ryan Reynolds. The actress first met him in 2010 on the set of Green Lantern. As co-stars, they got to spend a lot of time together, up close and personal. And they liked what they saw!
Marriage and family was a no-brainer for both of them, pretty quickly. According to Blake: "We've never gone a week without seeing each other. There's no major decision that I make without him. The best part is when we turn off our phones and just talk and hang out.'' Sounds like an upgrade, for sure! Would Leo also find something similar, soon?
Fling: Alyce Crawford
Well, not quite yet. Rumors swirled that Leonardo was involved with yet another model just days after his split from Blake. Perhaps he took it hard! At this point, the actor was filming The Great Gatsby in Australia. Who was the lucky lady, this time?
Eagle eyes noticed Leo cozying up to model Alyce Crawford, a local gal. The 21-year-old former Australian Next Top Model Contestant was seen many times at his hotel! But this wasn't his only fling during his stay in the outback. Who else did the actor get to know over there?
Fling: Madalina Ghenea
It's rare, but sometimes Leo does talk to brunettes. This time, he wanted to chat with Romanian model Madalina Ghenea. As a famous face in fashion, she is also involved in activism. Leo himself funds a few pet causes. Maybe they had a lot in common?
Madalina often describes herself as a citizen of the world, and fluently speaks 5 languages. She joined "Artists for Peace and Justice" for Haiti and renovated the maternity ward in the hospital of her hometown. Mada spent Leo's birthday with him! But it went nowhere after filming was completed in Australia. Perhaps Leo's passion is more environmental?
Relationship: Erin Heatherton
Back to blondes, Leo was ready for another real love. Yet another Victoria Secret model, Erin Heatherton dated the actor for about a year, from 2011 to 2012. Staring in 2010, she walked runways and shot campaigns for the brand. Some might say she was a real fan favorite!
For whatever reason, Leo didn't it was meant to last forever. Erin remains fond of him, though: “He’s a wonderful person and he’s a friend of mine, I wish him all the best.” Which Victoria's Secret angel would be next?
Fling: Miranda Kerr
Why, none other than Miranda Kerr! The first Australian Victoria's Secret model caught Leonardo's attention, at least for a short time. But she was taken, and quite publically by Orlando Bloom — a friend of his. Miranda was his baby mama, too!
After three years of marriage, the couple divorced. Rumors swirled that Leo and Miranda were dating as they were spotted all over NYC. Was it true? No one can confirm, but Miranda quickly got remarried to billionaire Snapchat CEO Evan Spiegel. Leo would also find a real girlfriend, next!
Relationship: Kat Torres
Kat Torres is a Brazilian model and influencer, and Leo's gal in 2013. They met at the Cannes film festival, and sparks flew! That was story for awhile, anyway. Recently, rumors have surfaced that the story may have been a PR stunt. Was it?
Kat said that Leo was very protective of his privacy. She explained: ''Leo is amazing, but I worry about what he will think about me talking to you. We have a pact that nothing can ever be said about our relationship.'' The mystery continues! But either way, Leo had someone else in his sights. Who, exactly?
Relationship: Toni Garrn
In terms of Leonardo DiCaprio's relationships, a year is pretty long. German model Toni Garrn is one of the few ladies to hold this title, in all of his dating history. From May 2013 to December 2014, they were seen all over the globe together. Who is she, exactly?
In 2011, Toni started modeling for Victoria's Secret! Yes, again. From the catalogs to the runways, the model had a good few years with the company in her early 20's. She was only 21 when she dated Leo, too! Who did the actor date next?
Relationship: Kelly Rohrbach
It was definitely time for more models. For around a year, Leo dated blonde bombshell Kelly Rohrbach. From 2015 to 2016, fans watched them closely. Rumors even swirled of commitment, believe it or not. Would there finally be an engagement in the Dicaprio dating story?
Their split in 2916 finally put those rumors to bed! But for Kelly, grieving was minimal. She quickly married attorney Steuart Walton, who happened to be a and Walton family heir. With a combined net worth of $200 billion — that's billion with a b — he hails from the richest family in the United States. How did Leo grieve?
It's not clear that he was so sad, really. But Leo did decide to try something different from his usual pattern. The headlines were everywhere, and some found it hard to believe. But it seems that Rihanna really was in his life, for a short time! Pictures proved it, and fans loved it.
Leo was under her umbrella, ella, ella, eh, eh, eh just for a short period. But it was something novel for him, dating history considered. Ladies everywhere wondered: Would he date more singers in the future, or return his model loving ways?
Fling: Nina Agdal
Indeed, it was back to the basics. And for Leonardo Dicaprio, his basic modus operandi was up and coming models. This time, he decided to court Danish beauty Nina Agdal. Repeatedly spotted around New York City, it was not a bad way to spend 2016!
According to Nina: ''I feel like people see me as this girl next door, and that comes across in my photos.'' Sports Illustrated, Maxim magazine, and Victoria Secret agreed! While it didn't go anywhere with Leo, her career has been pretty solid. Who did Leo chat up after Nina?
Fling: Laura Whitmore
It was simply a fact that Leo had neglected Ireland on his bucket list of beauty. After he met Laura Whitmore, he knew he had to try it! The Irish presenter, model, and actress is known for all kinds of European TV roles. From Survival of the Fittest to Love Island, people definitely know her face overseas!
After meeting at a party, they had a fling in 2016. As a tall, blonde, young famous woman, she fit his type quite well. It was quick, though. Leonardo was not done dating early 20's models!
Fling: Lorena Rae
In 2017, paparazzi found Leo with German model Lorena Rae. Who is she, though? In an interview, she recently described herself as follows: “Quoting my friends, they say I’m down to earth, always up for new things, I put family first and I’m very disciplined.” Perhaps that's how she made it to the runway at the Victoria's Secret Fashion Show!
Leo and Lor were spotted having a lunch date in NYC. They were seen riding CitiBikes together, too! Rumor has it that this is a favorite activity for the actor to try with his real girlfriends. But in the end, it was short-term between these two. Leo moved on, and fast!
Fling: Juliette Perkins
Had Leo ever dated anyone from New Zealand? Perhaps he realized the answer was no and got together with Kiwi model Juliette Perkins. It was nothing surprising for this fellow to be seen with a young blonde. This was a bit controversial though: Mid 40's Leo was now dating a 19-year-old!
A 23 year age difference was not illegal, of course. But she was even younger than his usual love interests! The pair didn't become serious, which surprised no one at all. Would his next flame be just as young and inexperienced?
Relationship: Camila Morrone
This time, Leo did try to subtract a few years from the gap! Since late 2017, Camilla Morrone has been the model in his life. Daughter of actress Lucila Solá and ex-stepdaughter of Al Pacino, she actually knows Hollywood quite well.
According to Cam: ''I was lucky because I grew up in Hollywood, so I didn't have a big illusion of what it was...Being raised in this industry from a young age definitely forces you to grow up a little faster than maybe the normal kid.'' Could this young lady be the one who finally captures Leo’s heart forever? Only time will tell — but no one's betting money on it!
The Wild Dating Life of Brad Pitt
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!
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 Dead, she 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 in the Babe sequel, and 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!
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?
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!
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!