Daily Times

CHRISTINA APPLEGATE — Pitt was the ‘Married With Children’ star’s date to the 1989 MTV Video Music Awards—and though she has remained mum on the subject, Skid Row rocker Sebastian Bach insists that he was the guy Applegate infamously ditched her up-and-coming-actor date for that night.

THANDIE NEWTON — Brad has described his experience making ‘Interview With the Vampire’ as “miserable”. He told Entertainment Weekly in 2011 that “the great thing that came out of that movie is that it birthed my love affair with New Orleans”. But the shoot also birthed a brief relationship with Newton, who had a small role as Yvette, a servant on Pitt’s character Louis’ plantation..

GWYNETH PALTROW — Pitt’s the one who lost his head for Paltrow on the set of 1995’s Se7en. They were the mid-90s couple, from the top of her slip dress to the ends of his frosted tips. Accepting the Best Supporting Actor Golden Globe for ‘12 Monkeys’ in 1996, Brad thanked Gwyneth, his “angel, the love of my life”, and he proposed that December. They even had matching haircuts at one point. “I take the institution extremely seriously. There are no divorces in my family either—and in his either, so this is not something—we’ve been together for quite some time, so this is not a rash decision,” Gwyneth convincingly told Entertainment Tonight about their engagement. But in June 1997, they broke up. “When two people aren’t supposed to be together, they’re not supposed to be together,” a defiant Paltrow said in 1998. Fast-forward to 2015, when she told Howard Stern, “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.” Moreover, her dad, Bruce Paltrow, was “devastated” when they broke up. “My father loved him like a son.” Ultimately, Paltrow said, “I definitely fell in love with him. He was so gorgeous and sweet. I mean, he was Brad Pitt!”

JENNIFER ANISTON — The story goes that Jen met Brad in 1998 on a blind date set up by their agents. The world still not one for smushed-together names yet, they were simply “Hollywood’s golden couple.” They married in 2000, Pitt guest-starred on ‘Friends’ in 2001 and in 2002 Aniston said of starting a family, “Absolutely it will happen but probably not for a while.” Alas, on January 8, 2005, the actors announced they had “formally” separated. “For those who follow these sorts of things, we would like to explain that our separation is not the result of any speculation reported by the tabloid media,” they said in a statement. The divorce was finalised that October amid all sorts of reports perpetuated by the people who do follow these sorts of things. Meanwhile, Aniston’s September 2005 Vanity Fair interview will go down in history as one of the rawest, most poignant break-up postmortems in celebrity history.

ANGELINA JOLIE — It took a few years, but the Oscar winner would ultimately indicate that she and Pitt had indeed fallen in love during the making of ‘Mr & Mrs Smith’ in 2004. Pitt went to Ethiopia with her when she adopted her second child, Zahara, in 2005—and he formally adopted Zahara and Maddox in 2006. Daughter Shiloh was born in May 2006, Jolie adopted Pax in 2007 and twins Knox and Vivienne were born in 2008. Spurred on by their kids, Brangelina finally married at their chateau in France in 2014 after being engaged for two years.