Brad Pitt's epic romantic history: 9 of his most famous former flames

Brad Pitt and Angelina Jolie. (Photo: Getty Images)
Brad Pitt and Angelina Jolie. (Photo: Getty Images)

Cape Town - Brad Pitt has found new love. However this time, the Hollywood heartthrob seems to be looking for a match out of the limelight – he’s rumoured to be dating MIT professor and architect Neri Oxman.

But the former one half of Brangelina and father of six has always been one of Hollywood's hottest bachelors. 

Throughout the late '80s and '90s Brad (54) was linked to nearly all of his famous co-stars – and he certainly cuddled up to plenty of them!

He eventually settled down with Jennifer Aniston (49) in 2000, but famously left her five years later for his Mr & Mrs Smith co-star, Angelina Jolie (42).

Of course, since his split from Angie in 2016 – with whom he shares kids Maddox (16), Pax (14), Shiloh (11), Zahara (13), Vivienne and Knox (both 9) – Brad is back on the market.

Here’s a look at Brad’s famous former flames…


Brad and British singer Sinitta Malone reportedly dated off-and-on for several years in the 80s. At the time, Sinitta (54) was the big star in the relationship, while Brad was still pretty B-list.

Juliette Lewis

She was just 17 years old when she started dating Brad, who was 10 years her senior.

The couple were together for three years, from 1990 to 1993. In an interview with Daily Mail in 2010, Juliette (44) said her relationship with Brad was a loving one.

“I was a teenager at the time. 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.”

Robin Givens

One of Brad’s earliest relationships was with Mike Tyson's ex-wife Robin Givens (53), from 1986 to 1987. Mike and Robin were reportedly estranged when she started seeing Brad. 

Jill Schoelen

In 1989 Brad briefly dated his Cutting Glass co-star Jill Schoelen (55) after his relationship with Robin. The pair was even engaged – but only for three months. Jill called it off after falling in love with a director, Brad reportedly told The Sun in 2011.

Christina Applegate

Brad bounced back from his broken engagement fast – he started dating Married with Children actress Christina Applegate (46) that same year. She was just 18 when she took him as her date to the 1989 MTV Movie Awards and famously ditched him for another man! While Christina has never revealed who it was, Skid Row rocker Sebastian Bach insists that he was the guy, E! Online reports.

Thandie Newton

Brad and Thandie (45) dated briefly in 1994, after they met on the set of Interview with the Vampire. They split amicably and are said to still be close pals.

Gwyneth Paltrow

One of Brad’s most high-profile relationships was with Gwyneth Paltrow (45) in 1994 – fans couldn’t get enough of the 90s It Couple. Brad popped the question in 1996 – but it all fell apart a year later. In an interview in 2016, the actress spoke candidly about her relationship with Brad, saying:  “I wasn't ready, and he was too good for me.”

Jennifer Aniston

Ah, who could forget Brad’s famous appearance on hit 90s sitcom, Friends? Certainly not Jennifer Aniston (49). It was then the couple met and fell head over heels in love, eventually tying the knot in Malibu in 2000. But in January 2005, Hollywood’s golden couple announced their separation – right around the time Brad met…

Angelina Jolie

Brad and Angelina (42) met on the set of Mr & Mrs Smith in 2004, and dated for a decade before they finally made it official. Of course, they called it quits just two years later, citing – what else? – irreconcilable differences.

Sources: Daily Mail, Cosmopolitan, E! Online,,Complex

(Pictures: Getty/Gallo Images)  

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