Hollywood legend Brad Pitt has made ladies worldwide weak at the knees for over three decades now (yes, he really is that old) and has amassed quite a collection of notches on his bed post. In a romantic, flowers and chocolates kind of way, of course.
Long before Brangelina, one of the most well-documented marriages in Hollywood, Pitt was seen as a bit of a heartbreaker. From pop sensation Sinitta through to the one that made us all cry (Jennifer Aniston), check out our list of ladies who have been lucky enough to snuggle up to the Fight Club star.
Way back in the early days of his career, Brad dated So Macho pop singer Sinitta. The pair were close for four years, with young Brad even escorting Sinitta to the 1988 Smash Hits Poll Winners Party. The couple remained close for some time before going their separate ways.
There does seem to be some overlap between the list of Brad’s lovers, so we’re not sure if Brad and Sinitta were on breaks or if Brad has been a little bit naughty (never!). Sinitta went on to have an on-and-off again relationship with music mogul Simon Cowell before finally marrying Andy Willner in 2005.
Robin Givens: 1986-1987, 1989
Brad decided to bite off more than he could chew when he got involved with Robin Givens. The couple first dated in 1986, before getting back together while Givens was married to heavyweight boxer Mike Tyson, who alleges that he found the couple in bed together! Tyson and his wife eventually filed for divorce, with him not being able to forgive the infidelity.
Givens went on to become a successful model and actress, posing for Playboy magazine and working on TV shows such as The Women of Brewster Place and The Fresh Prince of Bel-Air. She then went on to appear in Off-Broadway shows and turned up in popular series Chuck.
Shalane McCall: 1987
Brad managed to land a small run on the TV show Dallas in 1987, where he played the boyfriend of Shalane McCall’s character, Charlie Wade. It seems that Brad is a bit of a fan of method acting, as it’s alleged he ended up dating Shalane in real life, too. Albeit briefly. Brad at the time was only 23 when he landed the role, which would be one of the first acting jobs of his career.
Two years after meeting Brad, Shalene married Trent Valladares, one of the musicians from the band Clyde and retired from Hollywood not long after. It is now thought that she works as a librarian.
Christina Applegate: 1989
Brad and Married with Children actress Christina briefly dated in 1989 before Brad was unceremoniously dumped by Christina mid-date. It all kicked off when the pair attended the MTV Movie Awards back in 1989. Christina, who was just 18 at the time, left the award ceremony with another man! There’s been plenty of speculation over who the other guy was, but recently SKID ROW singer Sebastian Bach has alleged that it was him.
Christina was just two seasons into Married with Children when she left Brad, and she later went on to work another eight years on the show. She carved a respectable acting career out for herself, landing roles in the movie Don’t Tell Mom the Babysitter’s Dead, The Sweetest Thing, and both of the Anchorman movies.
Jill Schoelen: 1989
Jill and Brad got together when they worked alongside each other on the horror movie Cutting Class. Brad was so serious about Jill that he proposed to her, but things weren’t meant to be. Rather than becoming Mrs. Pitt, Jill ended up dating the director of another movie she was cast on and dumped Brad just three months after becoming engaged. Now that’s harsh.
Brad wasn’t the only high-profile partner of Schoelen’s. Before meeting Brad, she dated Keanu Reeves, who she met on the set of the movie Babes in Toyland. She would later go on to marry Anthony Marinelli, a film composer, and retire from stardom to become a mother.
E.G. Daily: 1989
If you’re a child of the ’90s, you may well know the distinct accent of E.G. Daily, but not necessarily the name. That’s because she was the voice talent behind Rugrats character Tommy Pickles, Buttercup from The Powerpuff Girls, and also of Smelly Cat in Friends. She also had a couple of acting turns, including playing Dottie in Pee Wee’s Big Adventure.
After her short-lived relationship with Brad, Daily went on to tour with a comedy routine about her life. She also embarked on a musical career and was last seen on The Voice in 2013, where she got through to the knockout rounds.
Juliette Lewis: 1989-1993
There was a ten-year age gap between Brad and Juliette when they first started dating. Brad was 27 whereas Juliette was still in high-school. The couple dated for four years after originally meeting on the set of their movie Too Young To Die? This wouldn’t be the last film that the pair starred in together, rekindling their on-screen connection in the movie Kalifornia in 1993. The pair had already split by the time the movie made it to the cinemas.
Like Brad, Juliette continued her acting career, working with Leonardo DiCaprio and Johnny Depp as well as movie legend Oliver Stone. She also launched a music career with her band Juliette Lewis and the Licks before deciding to go solo in 2009.
Geena Davis: 1991 (allegedly)
Geena Davis and Brad Pitt allegedly got together while working on Thelma and Louise, and if the explosive sex scene that they had in the movie is anything to go by, we can’t say we blame them. Whether Brad and Geena actually hooked up or not is uncertain, but one guy is adamant that they did – Brad’s ex-roommate Jason Priestley, who alleged the pair were meeting up in secret.
The film and TV successes kept coming for Geena, much like they did for her co-star Brad. She appeared in the movie Angie, where she played the title character, The Long Kiss Goodnight, and all three Stuart Little movies. She went on to marry twice since meeting Brad, with the second marriage to her plastic surgeon husband taking place in 2001.
Julia Ormond: 1993 (allegedly)
This is another case of meeting a partner on set for Brad (we see a pattern emerging here). It’s thought that when Brad and his Legends of the Fall co-star met in 1993, they not only played a couple on-screen but off it as well. It that’s the case, Julia was married to her spouse Rory Edwards at the time. The pair divorced in 1994.
British actress Julia went on to star with Brad again in the movie The Curious Case of Benjamin Button, a role which saw her nominated for a SAG award. After her divorce from actor Rory Edwards, Julia went on to marry Jon Rubin, a political activist. The pair remained together until 2008.
Jitka Pohlodek: 1994
Remember when Brad had long blonde hair that made him look like Kurt Cobain crossed with a mountain man? Well, it was about this time that he reportedly had a brief encounter with Jitka, too. The pair even attended the Legends of the Fall premiere together, but the relationship seemed to peter out not long after that. Shame, we think they made a handsome couple!
It’s thought that Brad first met Jitka when she was working at a car rental counter at LAX airport. She went on to have a small part in the movie Sugar: The Fall of the West. It’s rumored that the couple went their separate ways thanks to Brad’s on-set shenanigans.
Thandie Newton: 1994
Another brief relationship of Brad’s was with film actress Thandie Newton, who he met on the set of Interview with the Vampire. Despite having a short-lived relationship, the pair is still friends after splitting amicably. The twosome were only photographed together once, giving some insight into the longevity of the relationship.
British actress Thandie went on to great success in her career, snagging a role alongside Tom Cruise in Mission: Impossible II. She also received a BAFTA for her role in the movie Crash. Oh, and who can forget her standout performance in TV series Westworld last year?! In 1998 she married writer and director Ol Parker, known for The Best Exotic Marigold Hotel. The pair remains together to this day.
Jennifer Aniston: 1998-2004
All eyes were on Hollywood’s sweetest couple when they tied the knot in 2000 after being an item for two years. However, not all fairytales come with a happy ending. The couple divorced in 2004 after Brad was found having an affair with his co-star Angelina Jolie (this sounds familiar). Jennifer was painted as the bitter ex for a while and fans of the couple wistfully looked back at the pairing like Brad was the one that got away.
Afterward, Jennifer moved on with her life and got married to Justin Theroux. They separated in 2018. More recently, Jen’s been known to see Brad at social events involving mutual friends. In 2020, the two were photographed greeting each other at the SAG Awards!
Gwyneth Paltrow: 1994-1997
Gwyneth and Brad met on the set of the movie Se7en and dated for almost three years before calling it quits. Despite being one of Hollywood’s brightest couples, they were not meant to be, with Gwyneth later saying that she was too young (22 at the time) to know what she was doing. She also confessed to needing a good five years to get the Hollywood heartthrob out of her head.
Gwyneth went on to have a long marriage to Coldplay singer Chris Martin, though the pair decided to call it quits in 2014. The divorced finalized last year. Gwyneth has also had an incredibly successful acting career, winning a Golden Globe and Academy Award for her role in Shakespeare in Love. She also starred in Shallow Hal alongside Jack Black and had burst into the Marvel universe in her recurring role of Pepper Potts.
Claire Forlani: 1997 (allegedly)
Yet again, on-screen tensions seem to have bubbled over into real life! British actress Claire and Brad allegedly had a brief encounter during their time on set together on movie Meet Joe Black, after playing on camera lovers.
Forlani forged an incredible acting career for herself after her time on Meet Joe Black. The following year she starred alongside Ben Stiller in Mystery Men, before working with the likes of Jackie Chan, Daniel Craig, and Elijah Wood in movie roles. On TV she had a starring role in the show Camelot playing King Arthur’s biological mother, Igraine. She is also happily married to Scottish actor Dougray Scott, who she met in 2007.
Sonita Henry: 1998 (allegedly)
Brad and British actress Sonita Henry supposedly hooked up in 1998 when Sonita’s career was just beginning to blossom. There has been no confirmation from either camp on whether the rumors of their relationship are true, with both parties keeping quiet about the alleged tryst.
Sonita’s career has picked up considerably over the past few years, with a role in the recent Star Trek reboot in 2009 as well as being cast in Chuck and Doctor Who. She currently has two movies in the pipeline that should be due to be released this year. She still remains a little-known actress, so hopefully that will all change in the near future.
Demi Moore: 1998 (allegedly)
It’s thought that Brad and Ghost actress Demi Moore hooked up in 1998 while Demi was going through a very public divorce with her long-time husband, Bruce Willis. The romance is said to have fizzled out quickly, but just makes us wonder what could have been…they would have made quite the celeb couple!
If we were going to list all of Demi’s achievements since meeting Brad we’d need a MUCH bigger article, so we’ll just say that the woman is a Hollywood legend with a resume reading like a wishlist for most starlets. After Demi’s split from Bruce Willis, she went on to marry Ashton Kutcher with the pair going their separate ways in 2013. Kutcher is now married to Mila Kunis.
April Florio: 2003 (allegedly)
April worked as a successful glamor model and bit-part actress when it was alleged that she had an affair with Brad Pitt while he was still married to Jennifer Aniston – something which she denies happened. It’s thought that the pair were introduced by George Clooney during a three-day holiday in Greece.
Whether or not the pair had a relationship or not will likely never be known, however like everything in Hollywood the rumors came to a head again following Brad’s split from Angelina Jolie in 2016. April has maintained that she intends to protect herself and her child from the publicity that has fallen at their feet, and for now, at least is keeping mum and denying the rumors.
Angelina Jolie: 2004-2017
Angelina was portrayed as a scarlet woman for a while following her and Brad’s relationship on the set of Mr. and Mrs. Smith which brought about the end of Pitt’s marriage to Hollywood golden girl Jennifer Aniston. The pair endured a long relationship, marrying in 2014 following Jolie’s cancer prevention treatment the previous year. The pair has six children together, three of which were adopted internationally.
Sadly, Brangelina split in 2016 after 12 years together. Their divorce was finalized in 2017. The couple is said to be working hard at being amicable so that their children remain a priority during their separation.
What’s Next For Brad?
Now that Brad is a free agent again, the world is literally his oyster when it comes to finding a new partner – after all, he is one of Hollywood’s most enduring leading men. But after such a long marriage we wouldn’t be surprised if Brad takes some time away from the spotlight and from the dating game to recover. Particularly with reports that he has lost a ton of weight since his heartbreaking split.
Despite this, there have been links between him and Kate Hudson, as well as suggestions that Margot Robbie is also in the star’s sights. By the looks of Brad’s dating history, we just need to wait until we see who his next movie co-star is going to be.
Brad And Jen At The 2020 SAG Awards
Although it’s public knowledge that Brad and Jen occasionally see each other socially, we rarely see pictures of these friendly interactions. At the 2020 Screen Actors Guild Awards, however, we got to see the former couple interacting after they had each won an award.
During Brad’s acceptance speech for Best Supporting Actor for Once Upon a Time in Hollywood, Brad humorously discussed the “challenge” of the role: “A guy who gets high, takes his shirt off, and doesn’t get along with his wife . . . it was a big stretch. Big.” Of course, the cameras cut away to catch Jen’s reaction! Here, we see the two saying hello at the ceremony.