Jennifer Aniston is America's sweetheart. The actress is the recipient of various accolades, including an Emmy Award and a Golden Globe Award. She is one of the world's highest-paid actresses. Aniston began working as an actress at an early age. She was 24 when she landed her first major film role came in the 1993 horror comedy Leprechaun.

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She later rose to international fame for her role as Rachel Green on the television sitcom Friends (1994–2004), for which she earned Primetime Emmy, Golden Globe, and Screen Actors Guild awards. She has since starred in numerous dramas and romantic comedies.

Her biggest box office successes include Bruce Almighty (2003), The Break-Up (2006) and Marley & Me (2008). She won critical acclaim for her roles in The Good Girl (2002), and Cake (2014). Aniston returned to the small screen in 2019, producing and starring in the hit Apple TV+ drama series The Morning Show.

Jennifer Aniston has received nearly as much attention on her personal life as she's had on her entertainment career. She was first married to actor Brad Pitt, to whom she was with for five years. She later married actor Justin Theroux in 2015, but separated in 2017. But did you know she once went on a date with Jon Stewart? Although it was a little crowded...

Brad Pitt And Jennifer Aniston Were Friends For Four Years Before A Relationship Formed

Brad Pitt and Jennifer Aniston were tabloid gold in the late 90s. The pair first met in 1994 via their managers, who happened to be friends. "He was just this sweet guy from Missouri, you know?” Aniston told Rolling Stone in 2001. “A normal guy.” But their relationship wouldn't turn romantic until four years later. At the time of their meeting, Pitt had just broken up with actress Gwyneth Paltrow and Aniston had called it quits with actor Tate Donovan. In 2004, their managers set them up for their first date.

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On November 29, 1999, while attending a Sting concert together, the Hollywood stars took the stage to show off Aniston's engagement ring. Pitt reportedly spent $500,000 on the ring which boasted a diamond set in a unique circular shape. The Aniston and Pitt wedding of 2000 was undoubtedly the celebrity wedding of the year. The couple exchanged vows on a bluff overlooking the Pacific Ocean in Malibu in front of 200 guests.

Aniston wore a low-back wedding gown by Lawrence Steele and the newlyweds danced to "The Way You Look Tonight." The wedding was complete with a 40-person gospel choir, lobster meal and champagne toast. Singer Melissa Etheridge performed, with the ceremony ending with a 13-minute firework show. The big day reportedly cost the couple roughly $1 million.

Jon Stewart Once Asked Jennifer Aniston Out On A Date

Jennifer Aniston has been named by PEOPLE as one of the most beautiful women in the world. So it's no wonder comedian Jon Stewart tried to shoot his shot.

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During an appearance on The Daily Show in 2010, Stewart reminded her that they’d shared a romantic Italian meal in New York City. The "date" took place more than a decade ago. But their recollections of the evening were somewhat different. “I asked you out,” Stewart said. “And it was lovely. I remember you brought so many of your friends. And I remember thinking, ‘She’s so excited to be on a date with me, she wants me to get to know her posse.""

But Aniston was slightly perplexed saying: “If I remember correctly, wasn’t it sort of like, ‘Hey, a group of us are going out, do you want to join?’" she replied. It was clear Stewart still has fond feelings for Aniston as he told her, “You were lovely then and lovely now.” Stewart went on to marry former veterinary technician and graphic designer Tracey McShane in 2000. They share two children.

Justin Theroux Was Overwhelmed By Jennifer Aniston's Fame

Jennifer Aniston and Justin Theroux first met in 2007 on the set of Tropic Thunder. But they didn’t start dating until 2011, when they co-starred in the movie Wanderlust alongside Paul Rudd. “I thought he was so sweet and very nice,” Aniston told PopSugar in 2012. “But I remember thinking he was very dark. At first, you think he could be like a serial killer, but he’s actually the nicest person in the world.”

Though he was a well-known actor and screenwriter when they started dating, Theroux was overwhelmed with Aniston's celebrity. “It’s a bit like going to a slightly different altitude,” he told GQ of their relationship in 2013. The pair got engaged in 2012 after one year of dating but waited three years to tie the knot. “We just want to do it when it’s perfect, and we’re not rushed, and no one is rushing from a job or rushing to a job,” the Morning Show actress told the Associated Press in July 2013. “And, you know, we already feel married.”

The pair finally walked down the aisle in August 2015. They hosted an intimate party at their California home, telling friends and family that they would be celebrating Theroux’s birthday. Instead, guests got to witness their union. However, less than three years after their wedding the pair decided to end their marriage.

“In an effort to reduce any further speculation, we have decided to announce our separation,” they told Us Weekly in a joint statement in February 2018. “This decision was mutual and lovingly made at the end of last year. “We are two best friends who have decided to part ways as a couple, but look forward to continuing our cherished friendship.”