Meanwhile, Jolie is going through a really tough time and is depressed because of the separation from Brad as per the reports.

Brad Pitt is one of the most popular and handsome actors of all time. He was last seen in Once Upon A Time In Hollywood opposite his pal and BFF, Leonardo DiCaprio. He won an Oscar also for ‘Best Supporting Actor’ for the same. He looked really handsome in the film and it was difficult to take your eyes off him.

Well, Brad’s good looks aren’t just popular among the fans but also Hollywood actresses. Brad has dated a few very popular names in the Hollywood industry. Not just Jennifer Aniston and Angelina Jolie, Brad has also dated actresses like Gywneth Paltrow Christina Applegate and Jill Schoelen.

From Jennifer Aniston To Angelina Jolie, Here’s The List Of FAMOUS Women, Brad Pitt Has Ever Dated

Here’s Brad Pitt’s dating timeline:

Sinitta (1984-1988)- The Toy Boy singer and Brad dated for almost four years. Yes, that’s a long time to invest in someone. Talking about Brad naked body on I’m a Celebrity, Sinitta said, “Hot. He was beautiful with the most amazing body. I saw him for two years. He was fun, he was young and very sweet.” The two attended the 1988 Smash Hits Poll Winners Party together.

Robin Givens (1986-1987)- For those of thinking that he was dating Sinitta till 1988, yes yes, Brad double-dated with Robin. Robin started dating Brad while she was married to Mike Tyson. The two of them were together despite being committed to some else. Well, that’s Brad for all of us. Isn’t it!

Christina Applegate, 1989: Christina Applegate was also a part of the popular sitcom, FRIENDS and played the character of Jennifer Aniston aka Rachel Green’s youngest sister, Amy Green. The two dated for a very short period of time and Christina took Brad as her date for MTV Movie Awards and left him halfway through the night for some other guy.

Christina Applegate

Jill Schoelen, 1989: Jill Schoelen was quite popular in Hollywood in those days. Brad started dating Jill immediately after Christina and two were engaged for three months until Jill started dating the director of another movie that she was working on and dumped Brad in the blink of an eye. SAD.

Jill Schoelen

E. G. Daily, 1989: After Brad apparently got ‘dumped’ by ex-fiance Jill Schoelen, he dated pop singer E.G. Daily who voiced for Tommy Pickles on Rugrats, NBD and also did a cameo in FRIENDS.

Juliette Lewis (1989-1993): Juliette was just 17 when she started dating Brad who was 27 then. Speaking about her relationship in 2010, Juliette said, “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.”

Genna Davis, 1992: Yes, one more overlap here. After all, it’s Brad. By now you should know that it’s his style. After starring in Thelma & Louise, the two started dating secretly and that’s according to Brad’s former roommate Jason Priestley.


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Thandie Newton, 1994: Thandie and Brad started dating after starring in the ‘Interview With The Vampire’ together and called it quits soon. The two friend-zoned each other and have been the same ever since.

Gwyneth Paltrow (1994-1997): Well, it was Brad who proposed Gwyneth in 1994. The two met on the sets on Se7en and Brad referred her as ‘angel’ and ‘love of my life’ in his speeches at the Golden Globes. The couple called off their engagement in just seven months and Gwyneth said in 2015, “I definitely fell in love with him. He was so gorgeous and sweet. I mean, he was Brad Pitt! My father was devastated [when we split]. 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.”

Jennifer Aniston (1989-2004): The two met first time on the sets of FRIENDS but didn’t really get along unless their agents set them up later in 1989. They dated for two years and got married in Malibu, 2001 in front of their close friends and family. Their wedding is one of the most lavish weddings in the history of Hollywood. Everything was going fine until Brad started filming ‘Mr. & Mrs. Smith’ opposite Angelina Jolie. Brad got involved with Angelina and cheated on Jen with her. Later in 2005, Brad and Jen announced their divorce and it left their fans sad.

Angelina Jolie (2004-2016): This is longest time that Brad has ever been with someone in his life. After all, it was Angelina Jolie, one of the most beautiful women in the world. The two dated for almost seven years and announced their engagement in April 2012. They have six children together and got married in August 2014. Things went upside down in their paradise soon and Jolie filed for divorce in 2016 leaving their fans in shock.

Going by the recent reports, Brad is trying to reconcile his friendship with his famous ex-girlfriend, Jennifer Aniston. Although there’s no official confirmation to the news and we are desperately waiting to hear from them soon.

Meanwhile, Jolie is going through a really tough time and is depressed because of the separation from Brad as per the reports. The couple is still fighting over the custody of their six children and let’s hope that everything gets settled soon between them.