Brad Pitt’s Ex-Girlfriends, Wives & Dating Timeline

Brad Pitt

Getty Brad Pitt and Jennifer Aniston attend the 26th Annual Screen Actors Guild Awards.

Brad Pitt has dated a number of women. Since he divorced Angelina Jolie, his dating life has been the topic of considerable interest.

Historically, Pitt tended to date within Hollywood’s A-List.

At the SAG Awards, there was talk about his warm embrace with Jennifer Aniston and he was seen watching her acceptance speech on a monitor.

Pitt spoke to Ellen DeGeneres in 2019 about his romantic exploits and Ellen mentioned that she also dated one of his ex girlfriends.

Here’s everything we know about the women Brad Pitt has dated, married, divorced and shown up with:

Brad Pitt’s Early Dating Career

Brad Pitt

Actors Brad Pitt and Claire Forlani.

Brad dated Don’t Tell Mom the Babysitter’s Dead actress Christina Applegate, who dumped him halfway through the MTV Movie Awards.

Applegate did not reveal to Watch What Happens Live the person for whom she dumped Pitt, though Sebastian Bach said it was him.

Pitt dated Simon Cowell’s friend, Sinitta, going to the 1988 Smash Hits Poll Winners Party together.

Pitt dated Robin Givens of The Fresh Prince of Bel-Air, the independent film actress Juliette Lewis, and E.G. Daily, the voice of Tommy Pickles in Rugrats.

Pitt Was Engaged to Gwyneth Paltrow

Brad Pitt

Actor Brad Pitt (L), nominee for best supporting actor for his role as ” Jeffrey Goines” in “12 Monkeys” and his companion Gwyneph Paltrow.

Pitt started dating Gwyneth Paltrow in 1994. They met on the set of the film Se7en. In 1996, the became engaged and Pitt called her “the love of his life” at the Golden Globes, becoming one of the most famous celebrity couples of the 1990s.

Paltrow told Howard Stern that her Pitt was “too good” for her and her father loved him and was heart broken when they broke up.

Pitt Married Jennifer Aniston

Brad Pitt

Brad Pitt (L) arrives with his girlfriend actress Jennifer Aniston (R) at the Shrine Auditorium.

Pitt married Jennifer Aniston in 2001, who he started dating in 1998. They divorced in 2004. Their agents set them up on a blind date.

“I will say this about Jen: She’s fantastic, she’s complicated, she’s wise, she’s fair, she has great empathy for others… and she’s just so cool,” he told Rolling Stone.

Their Malibu wedding cost more than $1 million. They were married on a Malibu estate with $20,000 worth of fireworks. Guests included Salma Hayek, Dermot Mulroney, Cameron Diaz, and Courteney Cox who signed confidentiality agreements.

Pitt & Angelina Jolie Were Married

Brad Pitt

Brad Pitt and Angelina Jolie attend a private reception.

Pitt got together with Angelina Jolie in 2004. His divorce from Aniston sparked controversy among his fans, prompting them to choose Team Aniston or Team Jolie.

“It became very clear to me that I was so intent on trying to find a movie about an interesting life, but I wasn’t living an interesting life myself. I think my marriage [to Aniston] had something to do with it: trying to pretend the marriage was something that it wasn’t,” he said.

Pitt and Jolie announced their relationship in a W spread that showed them playing house in Palm Springs. They had six children.

Pitt and Jolie lasted 12 years. “When someone asked me why Angie and I don’t get married, I replied, ‘Maybe we’ll get married when it’s legal for everyone else.’ I stand by that, although I took a lot of flak for saying it—hate mail from religious groups. I believe everyone should have the same rights. They say gay marriage ruins families and hurts kids. Well, I’ve had the privilege of seeing my gay friends being parents and watching their kids grow up in a loving environment,” Pitt told Parade.

Jolie filed for divorce in 2016. Pitt told GQ about their divorce in 2017.

“The avoidance of pain is a real mistake. It’s the real missing out on life. It’s those very things that shape us, those very things that offer growth, that make the world a better place, oddly enough, ironically. That make us better. By the way, there’s no love without loss. It’s a package deal.”

Brad Pitt, the Divorcee

Brad Pitt

Actress Kate Hudson attends “The Reluctant Fundamentalist” Premiere.

Since his divorce from Jolie, Pitt was linked to MIT professor Neri Oxman, who denied the romance (she’s dating a hedge fund billionaire).

He’s also been linked to Kate Hudson, Sweetbitter starlet Ella Purnell and Sienna Miller.

Did Pitt Date Charlize Theron?

Brad Pitt

Charlize Theron attends “Bombshell” New York screening.

The Sun reported that Pitt dated actress Charlize Theron, saying they met through Theron’s ex Sean Penn and were seen at the Chateau Marmont in LA after attending film screenings separately.

A source told the newspaper, “They have been casually seeing each other for nearly a month now. They’ve been friends for some time — ironically through Sean — but things have developed.”

Theron, if she was dating Pitt, is not any longer. It is reported that Pitt is seeing many different women at the same time.

“He picks up his ladies on his motorcycle, which they love, and has wined and dined them at friends’ restaurants where he can enter through the back door and enjoy an old-fashioned date in a private dining area,” a source told In Touch.

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