Brad Pitt’s Girlfriends

Before being married and divorced twice, Holywood good looker Brad Pitt, had his fair share of famous girlfriends, most of whom have made their own headlines for different reasons.

Throughout the late ’80s and ’90s, the now, father of six changed his girlfriends as often as he changed his clothing as the names in his little black book grew. Here’s a brief peep at some of the more prominent ones.

1 – Sinitta

Sinitta Brad
Daily Star

Brad and American singer Sinitta were a serious item between 1984 and 1998.

At the time, he was in the early stages of his movie career and she was a pop singer.

She was once in a relationship with British singing star David Essex. Was married to Andy Willner until they split when he went to live in hong Kong and she was also engaged to Simon Cowell.

Of her romance with Brad, she says. ‘‘I saw him for two years. He was fun, he was young, very sweet and a great kisser.’’

2 – Robin Givens

Robin Givens
E News

Brad dated Robin Givens, a professional American actress, from 1986 to 1987.

Robin’s first introduction to Hollywood was when she appeared on the American sitcom, The Cosby Show (1984). At the time it was the hottest show on television. As a result of the role, she and comedian Bill Cosby forged a great friendship which would prove instrumental in Robin’s future career.

Later in life, she was married to boxing legend Mike Tyson which ended one year later on Valentines Day with irreconcilable differences given as the reason.

It’s rumoured that Brad was seeing her while she was still married to Mike Tyson. Oooch!

3 – Jill Schoelen

Jill Schoelen

In 1989, Brad met American actress, Jill Schoelen, on the set of horror movie Cutting Class. It didn’t take long for Brad to propose and they were soon engaged.

Three months later, Jill was filming ‘Phantom Of The Opera’ in Budapest and begged Brad to visit her.

Brad claims that at the time, he used his last $600 to make the journey, only to be told by her over dinner the night he arrived, that she had fallen in love with her current movie director and Brad was history.

Their engagement only lasted three months and it wasn’t to be Brad’s only heartbreak.

4 – Christina Applegate

Applegate Pitt
Pop Sugar

A few months later in 1989, following his brief engagement and subsequent dumping by Jill, Brad began seeing Christina.

On a night that should have been a whole heap of fun, Brad was Christina’s date at the MTV Movie Awards.

They had hardly finished posing for the Paparazzi, when Christina dumped him for another guy.

1989 wasn’t a great year for Brad and it looked like he would have to wait awhile before he found true love.


5 – E.G. Daily

E.G. Daily
My Daily Viral

After being dumped by Jill and then Christina, Brad met E.G. Daily and they dated briefly in 1989.

She has become an accomplished actress, voice artist, writer and singer and in 1986, her song ‘Say It Say It’, made the Nr 1 spot on the Billboard charts. But she is probably best known for her voice acting role as “Tommy Pickles” in the animated children’s series Rugrats in 1990.

When she and Brad hooked-up he was a young, promising actor trying to forge a career in Hollywood.

Their relationship didn’t last long, but they remained friends throughout the years and when asked about him recently she said. ‘He was my friend, he was always sweet and was a very generous doll.

6 – Juliette Lewis

Juliette Lewis
Huff Post

After splitting with E.G. Daily, Brad soon met Juliette Lewis when the couple Co starred in the movie, Too Young to Die. The couple were soon dating. Brad was 27 and Juliette was 17.

Their relationship lasted almost four years and they starred in several films together and the two have remained fond of each other.

When asked about her in an interview in 1994, Brad said, “I still love the woman.”

In 2010, Juliette said, “It amazes me that people are still fascinated that we went out for four years. 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.”

7 – Geena Davis

Geena Davis

After his breakup with Juliette, Brad met American actress Geena Davis when in they Co starred in the movie, ‘Thelma & Louise’.

Initially, Brad was second choice for the part after Billy Baldwin had secured the role, only to drop out later. As a result, Brad got the chance to audition again.

Brad’s role required an actor with a special mix of talent and laid-back sexiness and during a steamy love scene in the Ridley Scott movie, Brad and Geena got hot and heavy.

The scene has been cited as the pivotal moment that defined Pitt as a sex symbol. It also placed him on the map in Holwood, as the sexiest grifter in film history.

The couple ended up dating for a year before moving on to other relationships.

8 – Thandie Newton

Thandie Newton
E Online

American actress, Thandie Newton, is best known in more recent times for her role in Westworld.

She and Brad met on the set of ‘The Vampire’ in 1994. She had a small role in the film which was filmed in St Louis.

Years later in an interview, Brad revealed that the only two good things to come out of the film was his newfound love for New Orleans and meeting Thandie.

After meeting on set, they dated for about a year. Their relationship was not long massively publicised.

8 – Gwyneth Paltrow

Gwyneth Paltrow
Harper’s Bazaar

It would seem that Brad had a tendency to date his co stars and Gwyneth Paltrow was yet another one in his long list of relationships.

The couple met while filming Se7en in 1994, and after dating for two years, they got engaged.

In his speech at the Golden Globes, Brad described Paltrow as ‘’his angel and the love of his life’’.

They remained an item for three years, when they called off their engagement and in 2015, Paltrow admitted. “I definitely fell in love with him. He was so gorgeous and sweet. At 22, I was such a kid. You can’t make that decision when you’re 22 years old. I wasn’t ready, and he was too good for me.”

9 – Jennifer Aniston

Brad and Jennifer

Brad and Jennifer Aniston, met in 1998 after being set-up on a blind date by their agents. What followed was a whirlwind romance and after dating for two years they got engaged and later married in 2000 in a lavish affair that cost well over $1million.

Four years later whilst filming Mr & Mrs Smith with Angelina Jolie, things started to go wrong in the marriage and the couple divorced in 2005.

The marriage breakup was thought to be linked to Angelina, but both stars denied any romance at the time. Later on however, they both admitted they had fallen for each during the making of the movie.

10 – Angelina Jolie


Despite the rumours, Brad and Angelina started seeing each other shortly after his divorce from Jennifer and their relationship was made public, when Angelina confirmed she was pregnant with his child in 2006.

They spent the next seven years together before getting married in a private ceremony in France in 2014.

In what seemed to be the perfect marriage, the Hollywood heartthrobs ended up having three of their own kids and adopting three more.

But in 2016, fans were shocked to learn that Angelina had filed for divorce, citing irreconcilable differences as the cause of the breakup.

After two and a half years, their messy divorce is finally nearing closure and with two new movies releasing soon, Brad will probably pull out that little black book of his and start dating again.