Ever since Brad Pitt split from Angelina Jolie, rumors of his relationship status have abounded. The bachelor poked fun at his new single life over awards season, cracking Tinder jokes and even reuniting with his ex-wife Jennifer Aniston in a sweet moment, although he took to the red carpet solo throughout it.
Pitt, who recently won an Oscar for Best Supporting Actor, is father to six children from his marriage to Angelina Jolie. In his awards speech, he dedicated his Oscar to “my kids, who color everything I do.”
Whether or not any of the rumors are true (Pitt has denied most of them - including with a joke at the Golden Globes ) the actor has already gone out with some of the most eligible women in Hollywood (including, of course, his marriage to Jennifer Aniston).
At the SAG Awards, he joked about his past relationships, saying his role in Once Upon A Time... In Hollywood was "a difficult part - the guy who gets high, takes his shirt off and doesn't get along with his wife. It was a big stretch."
After his win, Aniston greeted him warmly backstage and he was spotted watching her own acceptance speech on a monitor.
Last year Pitt spoke to Ellen DeGeneres about his love life and the talk show host casually revealed she once dated one of Pitt's ex-girlfriends - although she didn't reveal who it was.
We'll leave you to guess from the list below...
Let's start with the flings
One of the 56-year-old's most memorable exes is Don’t Tell Mom the Babysitter’s Dead actress Christina Applegate, who famously ditched him halfway through the MTV Movie Awards for another man.
Applegate refused to reveal just who she had ditched Pitt for when she went on Watch What Happens Live, pleading the fifth when asked to clear up the decades-old mystery, though Sebastian Bach has claimed it was him.
In the early years, Pitt also dated singer and friend of Simon Cowell, Sinitta. The pair attended the 1988 Smash Hits Poll Winners Party together.
He also dated The Fresh Prince of Bel-Air actress Robin Givens, indie starlet Juliette Lewis, and most importantly, E.G. Daily, who voiced Tommy Pickles in Rugrats.
"I'll tell you what I've learned in my span of dating...If Madonna's Truth or Dare is her favorite, run. Run. If she was taking notes during the Sharon Stone cross-your-legs scene in that hit movie, run. Run!'" he told Rolling Stone about this period. Perhaps he was just feeling salty after the VMAs ditch.
Along came Gwyneth
Pitt began one of his most famous relationships in 1994 when he started dating Gwyneth Paltrow. The pair met while filming Se7en and got engaged in 1996. Pitt even called her “the love of his life” at the Golden Globes, cementing their pairing as one of the hottest celebrity couples of the 1990s.
"We just wanted to keep it special. Keep it ours,” Pitt told Rolling Stone about their relationship.
Paltrow later famously told Howard Stern that her ex was “too good” for her. Her father was “devastated” when they broke up and loved him “like a son.”
Pitt's long-term relationship with the Goop goddess was followed by his marriage to everyone's favorite friend, Jennifer Aniston, who he was with from 1998 until they split in 2004. The two met when 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 2001 Malibu wedding was wildly elaborate and cost more than $1 million. They were married on a multimillion dollar Malibu estate overlooking the Pacific with $20,000 worth of fireworks overhead. Guests including Salma Hayek, Dermot Mulroney, Cameron Diaz, and Courteney Cox signed confidentiality agreements ahead of the big day.
But Hollywood's fairytale marriage was sadly not to last. Pitt linked up with his Mr & Mrs Smith co-star Angelina Jolie in 2004. The split was controversial - fans chose teams, opting for Team Aniston or Team Jolie tees to show their loyalty. Even Paris and Nicky Hilton got in on the action with matching Kitson baseball tees.
“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. Ouch.
Brad and Angelina infamously announced their relationship in a W spread where they played house in Palm Springs - it was certainly foreshadowing, as they went on to have six children. "There’s a sensitivity chip that’s missing," Aniston famously said about the spread.
Mr & Mrs Pitt
Pitt went on to be with Jolie for 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 in 2009 about waiting to tie the knot.
“To be in love with someone and be raising a family with someone and want to make that commitment and not be able to is ludicrous, just ludicrous,” he said to the Hollywood Reporter.
He went on to speak out about his wife in interviews, whether it was her mothering skills (A+) or her bad girl tendencies - although she wasn't snapped kissing her brother on the red carpet again. "She's still a bad girl, delightfully so. It's not for public consumption,” he said about their relationship.
"One of the greatest, smartest things I ever did was give my kids Angie as their mom. She's such a great mom. Oh, man, I'm so happy to have her. With a partner like Angie, I know that when I'm working, the kids are happy, safe, and prospering. And when Angie's working, she knows she has the same,” Pitt went on tell Parade in 2011.
Ultimately, Jolie filed for divorce in 2016 - and it was messy. Accusations flew, culminating in an interview in GQ where Brad opened up about the split.
“For me every misstep has been a step towards epiphany, understanding, some kind of joy. Yeah, 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,” he told GQ after his split in 2017.
Life as a divorced dad
Since their divorce, the two-time recipient of People's Sexiest Man Alive hasn't confirmed any of his rumored love interests - guess they heard you do not talk about Fight Club... He was momentarily linked to MIT professor Neri Oxman, until she outrightly denied it (she's dating a hedge fund billionaire instead.)
He's also been linked to Kate Hudson, Sweetbitter starlet Ella Purnell, and Sienna Miller.
Obviously we're still holding out for a Jen reunion...
Did Brad Pitt date Charlize Theron?
It's been claimed by The Sun that Brad Pitt dated actress Charlize Theron. According to the newspaper, the pair met through Charlize's ex Sean Penn and reportedly were seen together at the Chateau Marmont in LA after attending film screenings separately.
The newspaper's source claimed, "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."
“They were ridiculously touchy-feely and his arm was around her back. At one point he winked at her," the source continued. "Brad seemed in a really good place — they both looked really happy.”
Theron has reportedly moved on, while Pitt allegedly continues to play the field, seeing multiple women at once.
“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. “He’s also taken one or two of them back to his art studio for intimate dinners and has gone hiking in Malibu on private trails behind the homes of some of his famous friends. Honestly, he hasn’t been this happy in years.”