Lucky in life and love! Jennifer Aniston‘s dating life has long been a topic of conversation — from her marriage to Brad Pitt to her relationship with her second husband, Justin Theroux.
Aniston and Pitt started dating in 1998 and tied the knot two years later. The twosome saddened fans when they announced their split in 2005 after five years of marriage. At the time, the Friends alum noted that there were “many stages of grief” when it came to their breakup.
“It’s sad, something coming to an end. It cracks you open, in a way—cracks you open to feeling,” she told Vanity Fair in September 2005. When you try to avoid the pain, it creates greater pain. I’m a human being, having a human experience in front of the world. I wish it weren’t in front of the world. I try really hard to rise above it.”
Shortly after the duo parted ways, Pitt started dating his Mr. and Mrs. Smith costar Angelina Jolie. The relationship raised eyebrows because the pair met when the Once Upon a Time in Hollywood star was still together with Aniston.
The Morning Show star, for her part, later got candid about how the rumors affected her, telling Vogue in December 2008. “There was stuff printed there that was definitely from a time when I was unaware that it was happening. I felt those details were a little inappropriate to discuss. That stuff about how she couldn’t wait to get to work every day? That was really uncool.”
In 2011, Aniston started dating Theroux after originally meeting four years prior on the set of Tropic Thunder. Although they got engaged the following year, the California native revealed that they weren’t in a rush to walk down the aisle.
“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 actress told the Associated Press in July 2013. “And, you know, we already feel married.”
The duo went to have an intimate wedding ceremony at their home in August 2015 after telling their loved ones that they were attending a birthday party for Theroux. Three years later, the couple announced their decision to part ways.
“In an effort to reduce any further speculation, we have decided to announce our separation,” they said in a joint statement to Us Weekly 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.”
Since the split, the Mulholland Drive actor has spoken highly of his bond with Aniston.
“I would say we’ve remained friends. We don’t talk every day, but we call each other. We FaceTime. We text,” he told Esquire in April 2021. “Like it or not, we didn’t have that dramatic split, and we love each other. I’m sincere when I say that I cherish our friendship. We can not be together and still bring each other joy and friendship. Also, she makes me laugh very, very hard. She’s a hilarious person. It would be a loss if we weren’t in contact, for me personally. And I’d like to think the same for her.”
The Emmy award winner, for her part, opened up about her positive outlook on her dating life, telling Elle in 2018, “My marriages, they’ve been very successful, in [my] personal opinion. And when they came to an end, it was a choice that was made because we chose to be happy, and sometimes happiness didn’t exist within that arrangement anymore.”
Scroll down to relive Aniston’s love life over the years:
Aniston and Schlatter sparked romance rumors after they worked on the short-lived 1990 TV adaptation of the John Hughes film Ferris Bueller's Day Off. Barry King/WireImage
The Dumplin’ actress called McDonald her “first love” in a January 2015 interview with The New York Times, saying, "He would have been The One. But I was 25, and I was stupid." Aniston and McDonald, who later died from brain cancer in 2007, dated for five years before they called it quits. Walter McBride/Corbis via Getty Images
The comedian and the actress went out on one date almost 20 years ago. “I asked you out and it was lovely,” Stewart reminded Aniston on The Daily Show in August 2010. “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.’” The Office Christmas Party star had a different memory of the incident and rebutted, “If I remember correctly, wasn’t it sort of like, ‘Hey, a group of us are going out, do you want to join?’” Frank Micelotta/Getty Images
Aniston and the Counting Crows frontman briefly dated in 1995. After their split, Duritz briefly moved on with Aniston’s Friends costar and real-life best friend, Courteney Cox. The Scream actress, for her part, has been in a relationship with Johnny McDaid since 2013. Ron Davis/Getty Images
Donovan was thrilled to land a six-episode arc on Friends in 1998, but the gig was bittersweet, as he and Aniston were in the middle of a split at the same time. “I was just happy to be on the team. The only bummer was Jennifer and I were breaking up at the time,” the Argo actor told Us in September 2018. “And so that was tricky to sort of act, and act like we are just meeting each other, and falling in love, or whatever, interested in each other, when we’re sort of breaking up. That was just tough.” Ke.Mazur/WireImage
The Object of My Affection costars played it coy about their rumored relationship for many years, but Aniston eventually admitted that the pair were “together when we were, like, 12.” The actors also appeared side by side in the 1998 movie The Newton Boys together, 2012’s Wanderlust and on Friends from 2002 to 2004. Ron Galella
Aniston and the Oscar winner started dating in 1998 and tied the knot in 2000. The actors shocked the world, however, when they separated in 2005 amid widespread rumors that Pitt cheated with his Mr. & Mrs. Smith costar, whom he began dating soon after his split from the Mother’s Day star. Pitt and Jolie, who share six kids together, separated after two years of marriage in 2016. They were declared divorced in 2019. Kevin Winter/Getty Images
The Cake actress moved on from Pitt with Wedding Crashers’ Vaughn, but the buzz surrounding the relationship ultimately caused it to end in December 2006. "You know, she’s great," the True Detective star told Playboy magazine in February 2015. "You like someone and you’re spending time with them; that’s separate and that was all fine. But I really spent most of that time finding ways not to be drawn into the attention." Aniston could also look back on the relationship with nothing but fondness and told Vogue shortly after the breakup, “He was lovely and fun and perfect for the time we had together. And I needed that. And it sort of ran its course.” Clive Brunskill/Getty Images
The British model romanced Aniston briefly in 2007, but their relationship never became serious. “There was no drama,” an insider told Us at the time. “They had a couple of dinners and hung out.” Gareth Cattermole/Getty Images
The singer and actress had an on-again, off-again relationship from April 2008 to March 2009. Following their final split, the “Gravity” crooner admitted on CBS Sunday Morning that he was “just a jerk” while they were dating. He later told Playboy: “That pearl of possibility that lives in your heart when you meet somebody you want to know more about has such a different molecular density than everything else that you have to pursue it. And I wouldn’t undo it, man. Because if it had worked out, I would have reaped the benefits. I would be sitting here saying, 'What I have when I go home is the thing I’ve always wanted.'" Kevin Mazur/VF/WireImage for Vanity Fair
Cooper and Aniston dated briefly in the summer of 2009 after starring together in He's Just Not That Into You. Their romantic relationship didn’t last long, but they always remained friendly. Jason Merritt/Getty Images for Spike TV
Dating rumors surrounded Butler and Aniston after they acted alongside each other in The Bounty Hunter. The Olympus Has Fallen actor later told Us that he and the Friends alum laughed off relationship speculation. “It’s a little bit ridiculous,” he said in July 2009. “But then you think, 'Oh, you know what … it's just silly.’” Kevin Winter/Getty Images
While Aniston and Theroux first met in 2007 on the set of Tropic Thunder and were introduced by the film's director and star, Ben Stiller, they didn’t start dating until after they reconnected while shooting Wanderlust in 2010. The pair went public with their relationship at the 2011 MTV Movie Awards and got engaged on the Spy Who Dumped Me star’s birthday in August 2012. They tied the knot three years later, but announced their separation in February 2018, saying that the “decision was mutual and lovingly made.” Kevin Mazur/VF15/WireImage
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