All Of Brad Pitt's Failed Relationships: A Timeline

Brad Pitt has consistently delivered throughout his acting career, scoring box office hit after hit — with a few exceptions — "Happy Feet Two," anyone? It's a whole different matter regarding Pitt's love life, though. The actor has a string of failed relationships to his name, and if gossip is to be believed, at some point, Pitt loved and lost every woman in Hollywood under 70.

Among the legion of purported lucky ladies is Sinitta. The singer, best known for the '80s hit "So Macho," claims she hooked up with Pitt during breaks from her longtime love, Simon Cowell. "We met and were literally, not in the way you think, rolling around the floor in the Albert Hall on our first date," Sinitta told Absolute Radio in August 2012. Another rumored ex is Robin Givens. Mike Tyson claimed he once rolled up at his then-wife's house (although they were going through a divorce at the time) and caught her getting cozy with Pitt. "I was mad as hell," he said on "In Depth with Graham Bensinger" in 2012 (via ABC News). "You should have saw his face when he saw me." However, according to Givens, Tyson's trippin'. "Never happened. Never, ever, ever happened," she told Andy Cohen on "Watch What Happens Live" in June 2019, admitting they were together but not in the romantic sense. "We were coming from like a screening or something," Givens insisted. 

So, who is an ex, and who isn't? We're going by the rule of thumb: if there is no photo, it didn't happen. So, with that in mind, check out a timeline of Pitt's (verified) failed relationships.

Jill Schoelen was the first of Brad Pitt's failed relationships. She was also his first fiancée and the first of many to break his heart. The actors met on the set of the comedy/horror film "Cutting Class." The movie was a bomb, scoring a paltry 13% on the Tomatometer. "Cutting Class is as bizarre as it is bad, which proves to be a slight saving grace," critic Matt Brunson quipped at Film Frenzy. Sadly for Pitt, the romance didn't fare any better.

Pitt claimed that three months into their engagement, a lonely Schoelen called and begged him to join her in Budapest where she was filming "Phantom of The Opera" in 1989. "She was lonely, and there was a huge drama. At this point, I had $800 to my name and I spent $600 of it getting a ticket from Los Angeles to Hungary to see her," he told The Sun. Pitt said he rushed to the set before taking her out to dinner where he had his heart broken: "She told me that she had fallen in love with the film director. I was so shocked I said, 'I'm outta here.'"

Adding to the indignity, it didn't last between Schoelen and the director. She met music composer Anthony Marinelli soon after. The couple walked down the aisle in 1993 but split nine years later. Still, Pitt didn't waste any time moping around. He was quickly back on the dating saddle once again and off to pastures anew.

Brad Pitt quickly moved on with Christina Applegate after his broken engagement to Jill Schoelen. However, things didn't fare much better for the budding movie star. In November 2012 Applegate told More magazine (via USA Today) that she used to invite Pitt and Jason Priestly over for BBQs when she was a teenager working on "Married with Children." And it wasn't only the steak that sizzled because she and Pitt struck up a hot romance.

But Applegate's fling with Pitt was over pretty much before it even started. The couple attended the MTV Music Awards together in September 1989 but left separately after Applegate dumped him for another guy — mid-ceremony — ouch. "Who was the guy you ditched Brad Pitt for?" Andy Cohen asked during a "Plead the Fifth" segment on "Watch What Happens Live" in August 2015. "I have to say it?" Applegate asked. "I don't have to do nothing!" Cohen peppered her with questions, but Applegate refused to spill. However, she denied that the mystery man was an actor, acknowledged he was famous, shared they didn't end up dating, and admitted she never saw Pitt again.

So, who was Pitt's replacement? "That would be me!" Skid Row front man Sebastian Bach boasted in an interview with "Elliot in the Morning" in December 2016. "That was the MTV Awards that night. She came with Brad Pitt and left with me mother drugger. True story!"

Next up on Brad Pitt's list of failed relationships was Juliette Lewis. The actors met while filming the 1990 TV movie "Too Young to Die?" when she was 17 and Pitt 27. Things got hot and heavy, fast, resulting in the couple moving in together. Pitt was Lewis' plus one at the 1992 Oscars, where she scored gold for her role in the crime horror film "Cape Fear." Then, in an eerie case of foreshadowing, they went on to play a murderously dysfunctional couple in the 1993 dark thriller "Kalifornia."

"We're like at the point in love where we just like to see each other every single day and we don't get bored with each other, so it's really, really nice. Also, we get to be around each other when we're working and . . . talk and collaborate," Lewis told The Los Angeles Times in January 1993. "We want to work together again and again and again."

Sadly, they never got the chance, as Pitt and Lewis split months later. "I still love the woman," Pitt told Vanity Fair in February 1995. "There's some real genius there. I had a great time with her. ... It was one of the greatest relationships I've ever been in. The problem is, we grow up with this vision that love conquers all, and that's just not so, is it?"

Sparks immediately flew when Brad Pitt and Gwyneth Paltrow met while making the 1995 crime thriller "Se7en." And by the time filming wrapped, Paltrow had lost her head and her heart. With their matching hair 'dos and frosted tips, Pitt and Paltrow were the consummate mid-'90s it couple. They were regulars on the red carpet and weren't afraid to express their love publicly.

When Pitt accepted his Golden Globe for Best Supporting Actor in January 1996 for the film "12 Monkeys," he thanked "the love of my life, my angel, Gwyneth Paltrow," in his acceptance speech. Eleven months later, Pitt popped the question. "I take the institution of marriage extremely seriously," Paltrow told Entertainment Tonight following the proposal. "There are no divorces in my family and in his either. We've been together for quite some time, so this is not a rash decision."

They broke up in June 1997. "It was great, and he's great, and he's a lovely guy, and it's like, for us, in the end, the relationship didn't work out. And it's fine, you know what I mean?" she told GMTV in 1998. However, in a January 2015 interview with Howard Stern, Paltrow blamed herself for the split from Pitt. "I was such a kid; I was 22 when we met. It's taken me until 40 to get my head out of my a**. You can't make that decision when you're 22 years old. ... I wasn't ready, and he was too good for me," she said.

It wasn't love at first sight for Jennifer Aniston and Brad Pitt when they met in 1994. "He was just this sweet guy from Missouri, you know?" Aniston told Rolling Stone in September 2001 of her initial impressions. "A normal guy." At the time, she was dating Tate Donovan and he was with Gwyneth Paltrow, but things took a romantic turn in 2000 once they were both single. It was a whirlwind romance; Aniston and Pitt were engaged within five months and married by August. They said "I do" in a romantic $1 million Malibu wedding with 200 guests; 50,000 roses, wisteria, tulips, and lotus flowers; lobster; loads of champagne; a wall of caviar; performances by Billy Preston, Melissa Etheridge, and a 40-person gospel choir; and fireworks.

"My friends were all supportive," Aniston said of her sudden marriage, "especially when they found out what a loving human being Brad is. At first, they're like, 'I hope he's not an a******." The marriage only lasted a few years. Pitt met his next wife, Angelina Jolie, on the set of their 2005 action/comedy "Mr. & Mrs. Smith."

Pitt denied cheating on Aniston with Jolie, although rumors of his infidelity circulated after he and Aniston split in 2005. Suddenly, Pitt and Jolie were making out like bandits, adopting orphans,  and posing for family-perfect photoshoots. "There's a sensitivity chip that's missing," Aniston told Vanity Fair in September 2005, admitting she'd always love him, though.

Brad Pitt's biggest failed relationship has to be with Angelina Jolie. Their romance was controversial and unconventional from the get-go — little surprise given they started hooking up while he was still married to Jennifer Aniston, despite their (many) cheating denials.

Brangelina moved at a breakneck speed, providing the tabloids with years of "Love Triangle!" headlines and front covers. They were snapped strolling on a Kenyan beach with Maddox Chivan in April 2005. Three months later, Zahara Marley joined the family. In May 2006, Shiloh Nouvel was born, and Pax Thien was adopted in 2007. Rounding out the Brangie clan, Vivienne Marcheline and Knox Léon arrived in July 2008. "Because of [Mr. & Mrs. Smith], we ended up being brought together to do all these crazy things, and I think we found this strange friendship and partnership that kind of just suddenly happened," Jolie told Vogue in January 2007 (via the New York Post).

There was endless wedding speculation and made-up reports. But Pitt vowed to Esquire in October 2006, "Angie and I will consider tying the knot when everyone else in the country who wants to be married is legally able." However, they said "I do" at their French chateau in September 2014, nine months before marriage equality was granted. It was all over by September 2016 when Jolie filed for divorce following an alleged altercation on a plane. A bitter custody battle ensued, and the war rages to this day.