The Actor Has Had Quite A Number Of Hookups And Breakups Through

Brad Pitt first stole our hearts when he made his first major film debut as a cowboy hitchhiker in Thelma & Louise. Since then, his roles on the silver screen have become ever more diverse, from playing Lieutenant Aldo Raine in Inglourious Basterds to his most recent Oscar win as Cliff Booth in Once Upon a Time in Hollywood. But perhaps even more diverse than his acting career is his long list of former flames.

1. Brad And Sinitta

British pop singer Sinitta and Brad Pitt were an on- and off-again couple in the mid-'80s, before he made it big with Thelma & Louise. After two years together, she eventually broke things off, but she looks back on their relationship with fondness. "He was beautiful with the most amazing body," she told Marie Claire. "I saw him for two years. He was fun, he was young and very sweet." When asked in 2016 what their cutesy supercouple nickname should have been, Sinitta jokingly remarked, "I like Braditta!"

2. Brad And Shalane McCall

When you work together, you inevitably spend a lot of time together and get to know your colleagues really well. That's apparently what happened with Pitt and Shalane McCall. They met on the set of Dallas in 1987, and reports quickly surfaced that they were seeing each other romantically. Did you even know that Pitt appeared on Dallas? He played Randy, the boyfriend of McCall's character, for four episodes on the show between 1987 and 1988. While Pitt's time on the show was brief, it didn't take long for the rumors to start swirling. However, McCall married musician Trent Valladares just a year after Pitt left the show.

3. Brad And Robin Givens

Robin Givens and Pitt first met in the '80s when he guest starred on her sitcom Head of the Class, and it was rumored that they struck up a romance sometime between 1986 and 1987.

4. Robin Givens

The two later went their separate ways, and Givens ended up marrying professional boxer Mike Tyson. In his memoir Undisputed Truth, Tyson alleged that he once caught Givens and Pitt in bed together while they were still married, but Givens has denied it. "I didn’t read the book," she said during an appearance on Watch What Happens Live with Andy Cohen. "But I was told he says he caught us in bed, which never happened. Never, ever, ever happened."

5. Brad And Jill Schoelen

Long before he was ever married to Jennifer Aniston or Angelina Jolie, Brad Pitt was engaged to Jill Schoelen. Pitt met Schoelen when they co-starred in Cutting Glass, a 1989 black comedy horror film that was a box-office flop. The two started dating shortly after the filming ended, and things moved swiftly. Not long afterwards, they announced their engagement.

6. Jill Schoelen

After just three months of being engaged, Schoelen ended things. According to Pitt, she called off their engagement after falling in love with a director.

7. Brad And Elizabeth Daily

In 1989, Brad Pitt was rumored to be in a relationship with Elizabeth Daily, also known as E.G. Daily. At the time, Pitt was still coming down from his tumultuous breakup with Jill Schoelen, so his relationship with the PeeWee’s Big Adventure star didn't last long.

8. Elizabeth Daily

After Daily and Pitt broke up, they remained friends, and Daily still thinks highly of the actor.  "He's very laid back, very earthy. He's the kind of guy that would pick up and leave and drive his car just to get out of the city," she told the Daily Mail. "He was never someone that was super Hollywood, he was a very calm and gentle guy.

9. Brad And Christina Applegate

Brad and Christina first met when she was a teen starring on Married With Children. Pitt and Jason Priestly would come over to her house for barbecues. The two started dating after they both guest-starred on 21 Jump Street.

10. Christina Applegate

Love was fleeting for Christina and Brad. Applegate took him as her date to the 1989 MTV Movie Awards only to famously ditch him for another man.

11. Brad And Juliette Lewis

In 1989, when Brad Pitt was still forging his Hollywood career, he and Juliette Lewis became smitten with each other while on the set of Too Young To Die. They dated for a little over four years, from the end of 1989 to 1993.

12. Juliette Lewis

Years later, Lewis only had good things to say about Pitt. "It amazes me that people are still fascinated that we went out for four years," she said in an interview with the Daily Mail in 2010. "I was a teenager at the time. It's a lifetime away. I was in my high school years and it was a wonderful, loving relationship with a fun, smart guy. Then it was over and he went on to become incredibly famous."

13. Brad And Geena Davis

Rumors of a relationship between Brad Pitt and Geena Davis started swirling after their sizzling sex scene in Thelma & Louise in 1991. According to Jason Priestly, Pitt's former roommate, the relationship between Pitt and Davis blossomed off-screen, but Davis wanted to keep it hush-hush.

14. Brad And Jitka Pohlodek

In 1994, Czech model Jitka Pohlodek accompanied Pitt to the premiere of Legends of the Fall. But not a lot seemed to come of it since Pitt quickly moved on to other women.

15. Brad And Julia Ormond

Julia Ormond met Brad Pitt on the set of the 1994 drama Legends of the Fall. The two shared some steamy scenes in the film, and rumors swirled that they were having a real-life romance off-screen. However, the two never publicly acknowledged the relationship.

16. Brad And Thandie Newton

There seems to be an ongoing theme here. Like a lot of celebrities, Pitt ended up dating plenty of his co-stars. Pitt and Thandie Newton met while on the set of the 1994 film Interview with the Vampire. They dated briefly for just about a year and then broke things off, but they reportedly stayed friends.

17. Brad And Gywneth Paltrow

Brad and Gywneth started dating after they met on the set of the 1995 neo-noir psychological crime thriller Se7en. They became a high-profile couple in the '90s, with Pitt calling Paltrow his "angel" and the "love of my life" after he won the Golden Globe for 12 Monkeys in 1996.

18. Gwyneth Paltrow

Pitt proposed to Paltrow in 1997 after two years of dating. But the fairytale romance wasn't meant to be. The couple broke up just seven months after they announced their engagement. 

19. Gwyneth Paltrow

Years later, Paltrow told Howard Stern: "I was such a kid. I was 22 when we met. It's taken me until 40 to get my head out of my ass. You can't make that decision when you're 22 years old... I wasn't ready, and he was too good for me."

20. Brad And Claire Forlani

Following his breakup with Paltrow, Pitt and Claire Forlani were briefly an item after the two met on the set of Meet Joe Black. Speculation about the romance hit an all-time high when the couple attended the 50th Annual Writers Guild of America Awards together in 1998.

21. Brad And Demi Moore

Pitt and Moore were reportedly an item very briefly in the '90s, shortly after Moore announced her separation from then-husband Bruce Willis. Rumors swirled that Moore and Pitt bonded over yoga, but those reports were never confirmed.

22. Brad And Jennifer Aniston

It seemed like a fairytale match. Aniston and Pitt were set up on a blind date by their agents in 1998, and the two instantly hit it off. At the time, Pitt was one of the hottest actors in Hollywood and Aniston was considered to be America's sweetheart, so it wasn't long before they became Hollywood's biggest supercouple.

23. Jennifer Aniston

In 2000, Brad and Jen tied the knot in a lavish Malibu wedding, complete with an elaborate fireworks show and a performance by Melissa Etheridge.

24. Jennifer Aniston

But the fairytale wasn't meant to last. Hollywood’s golden couple formally announced their separation in January 2005 after five years of marriage. They have since become friends again.

25. Brad And Angelina Jolie

Brad Pitt and Angelina Jolie first met while filming 2005 action comedy Mr. and Mrs. Smith. Although they both initially denied the relationship rumors, it later came out that they "fell in love" while Pitt was still married to Aniston.

26. Brangelina

After seven years together and six children, Hollywood's golden couple got engaged in 2012. Their engagement lasted two years, and in 2014, Jolie walked down the aisle wearing a white dress and veil featuring her children's colorful drawings.

27. Angelina Jolie

After 11 years of being together, in late 2016, Jolie filed for divorce, citing "irreconcilable differences." In multiple interviews, she's stated that the separation was for "for the health of the family." As part of the divorce proceedings, she requested sole physical custody of their six children, Maddox, Pax, Shiloh, Zahara, and twins Vivienne and Knox.

28. Brad And Sienna Miller

Following Pitt's divorce from Jolie, various media outlets started reporting that Brad and Sienna Miller had been "spending some time together." That escalated into rumors that the two were in a romantic relationship. However, Miller later set the record straight and dismissed those rumors as "predictable and silly."

29. Brad And Nicole Poturalski

Brad Pitt and German model Nicole Poturalski were first spotted together in late 2019 when they attended Kanye West’s opera performance together at the Hollywood Bowl in L.A. Later they were seen arriving together at the Le Bourget airport in France on their way to Pitt's chateau in the region. The two quietly dated for several months but then went their separate ways.