Brad Pitt's Love Life in 8 Photos

The World War Z star has dated (and been engaged to) a number of A-list ladies, including a few who may surprise you!

Nowadays, when you think of Brad Pitt and his personal life -- you can only think of his fiance Angelina Jolie and their brood of six beautiful children. But it wasn't always this way.

Before the hunky actor started his family, and even before Jennifer Aniston entered his life, there were quite a few starlets that caught his eye. Let's take a look back at Brad's romance history.


Robin Givens (Dated 1988)

Brad Pitt, Robin Givens

Vinnie Zuffante/Archive Photos/Getty Images

Relationship highlight: Before he was a movie star, Pitt paid his dues with short stints on TV shows, like the sitcom Head of the Class. While filming a guest spot (check out his scenes here), Pitt fell for cast member Givens.

How it ended: Brad and Robin dated for six months, but her estranged husband Mike Tyson wasn't over her -- which created some problems. "We would go on dates and we'd come back to my house and Michael would be standing out there ... and it would scare [Brad]," Givens said on The Howard Stern Show. "And then we'd have to go to his house, you know what I mean? It just got crazy." Tyson, for his part, claims he once walked in on the couple having sex.

Christina Applegate (Dated 1988)

Brad Pitt, Christina Applegate

Barry King/WireImage

Relationship highlight: Having been friends for a few years, 18-year-old Christina and 25-year-old Brad decided to give romance a try. ("We kinda looked at each other and went, 'Hmmm, kinda cute,'" recalls Christina.) Their first big outing as a couple was the 1989 MTV Video Music Awards, where Applegate presented the Best Group Video award with Alice Cooper.

How it ended: "We went to the MTV Awards and I ditched him!" Applegate confessed in a 2005 interview. "I left him there and I felt really bad about it, I really, really do. I left with somebody else."

Juliette Lewis (Dated 1989 - February 1993)

Brad Pitt, Juliette Lewis

Ron Galella/WireImage

Relationship highlight: While shooting the 1990 TV movie Too Young to Die?, Pitt began a very intense relationship with his very young co-star. (Juliette was 16, Brad 26.) Four years later, the couple co-starred in the serial-killer movie Kalifornia. "You do a scene and then go over and grab the one you love," Pitt gushed to the LA Times during a set visit.

How it ended: The up-and-coming actors broke up shortly after making Kalifornia, but Pitt continued to carry a torch for her. "I still love the woman," he told Vanity Fair in 1994. "The problem is, we grow up with this vision that love conquers all, and that's just not so, is it?"

Jitka Pohlodek (Dated 1994 - 1995)

Brad Pitt, Jitka Pohlodek

Ron Galella, Ltd./WireImage

Relationship highlight: Pitt met the aspiring actress at an airport car-rental agency, and not long afterwards, they were walking down the red carpet (in boots and jeans!) at the Legends of the Fall premiere.

How it ended: Jitka and her pet bobcats moved in with Pitt in 1995, but they didn't stay for long -- reportedly because she'd heard rumors that Brad was hooking up with his co-stars.

Jill Schoelen (Began dating 1988; Engaged March 1989; Broke up June 1989)

Brad Pitt, Jill Schoelen

Ron Galella/WireImage

Relationship highlight: Brad and Jill were co-starring in the 1989 slasher film Cutting Class when they began dating.

How it ended: While shooting a film in Hungary, Pitt's fiancee called him in tears. "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," Pitt told The Sun. Turned out that Jill was leaving him for the film's director.

Gwyneth Paltrow (Began dating 1995; Engaged December 1996; Broke up June 1997)

Brad Pitt, Gwyneth Paltrow

Kevin Mazur Archive/WireImage

Relationship highlight: At the height of their romance in 1996, Pitt brought Paltrow (who broke up with Donovan Leitch while she and Pitt were shooting Seven) to the Golden Globe Awards. Upon accepting his Best Actor statue for Twelve Monkeys, he thanked Gwyneth, calling her "the love o' my life, my angel."

How it ended: Shortly after the golden couple's unexpected split, People reported that Brad was "commitment-shy" and "changed his mind" about the engagement. Gwyneth has since said that she felt responsible, telling Diane Sawyer, "My kind of internal stuff really tripped up that whole relationship."

Jennifer Aniston (Began dating May 1998; Engaged 1999; Married July 29, 2000; Separated Jan. 6, 2005; Divorced Oct. 5, 2005)

Brad Pitt, Jennifer Aniston


Relationship highlight: Engaged twice before, Pitt walked down the aisle for the first time with Aniston. Their Malibu wedding was a true Hollywood spectacle, with 200 guests (including the cast of Friends), 50,000 flowers, four bands, a 40-member gospel choir, fireworks, and a slate fountain custom-built for the occasion. The couple composed their own vows, with Pitt promising to always "split the difference on the thermostat."

How it ended: Why did these two break up again? Just kidding. Angelina Jolie came between them, obviously, though we'll never know when she and Brad made the leap from flirtatious co-stars to something more. In 2011, Pitt said that he spent his years with Aniston "trying to pretend the marriage was something that it wasn't."

Angelina Jolie (Began dating 2005; Engaged April 2012)

Brad Pitt, Angelina Jolie

Tim P. Whitby/Getty Images

Children: Maddox and Zahara, adopted by Pitt in 2005; Shiloh, born 2006; Pax, adopted 2007; Vivienne and Knox, born 2008

Relationship highlight: Brad and Angelina debuted twins Vivienne and Knox, their second and third biological children, on the cover of People. Sold for $11 million, the pictures moved 2.6 million magazines and hold the world record for the most expensive baby photos of all time. Since it's Brad and Angelina we're talking about, the profits went entirely to their children's charity, the Jolie-Pitt Foundation.

Donna Kaufman is an iVillage contributing writer. Find her on Google+.

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