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: