Before she officially becomes the first-ever Mrs. Justin Theroux, MTV News is remembering some of her most memorable romances of this millennium, from Brad Pitt to John Mayer.
Brad Pitt, 1998 to 2005
Brad and Jen married in Malibu in May 2000 after two years of dating. After five years of holy matrimony they split, sparked by rumors of his infidelity with his current fiancé Angelina Jolie.
Aniston, in 2005, had some choice words for her ex. In an interview with Vanity Fair she shared, "There is a sensitivity chip that's missing. I just don't know what happened. ... I feel as if I'm trying to scrounge around and pick up the pieces in the midst of this media circus."
Despite splitting seven years ago, the love triangle continues to make headlines. In fall 2011, the threesome made news after he said that his life with Aniston had become dull.
"It became very clear to me that I was intent on trying to find a movie about an interesting life, but I wasn't living an interesting life myself," he told Parade. He later issued an apology to his ex-wife, saying, "It grieves me that this was interpreted this way. Jen is an incredibly giving, loving and hilarious woman who remains my friend. It is an important relationship I value greatly."
Vince Vaughn, 2005 to 2006
After her breakup with Pitt, she met Vaughn on the set of their film called, well, "The Break-Up." They started dating in the summer of 2005. But even as romance rumors swirled around them, Aniston denied anything was going on between the twosome, sharing, "I adore Vince Vaughn, but I'm not going out with Vince Vaughn."
Eventually they went public. In May 2006, Vaughn opened up to Oprah Winfrey about his lady, saying, "Jennifer's great." He further shared, "She's just really smart and funny and easy to be with — very considerate. She's great." During the same interview, he joked that he and Aniston had yet to have discussions about kids, laughing, "First we have to have the $8 million wedding."
However, things eventually ended between the pair when they confirmed their split in December of that year.
John Mayer, 2008 to 2009
After a brief romance with model/actor Paul Sculfor, Aniston found love with pop's premier romancer John Mayer. They kicked off a rocky relationship in February 2008 before breaking up in August only to get back together again in October.
After their reunion, Aniston spoke to Vogue about the seemingly odd pair. "People need to mind their own business!" she said. "Did you ever think Claudia Schiffer and David Copperfield made sense? Love just shows up."
They really did split for good in April 2009. In early 2010, he shared with Rolling Stone that he was still nursing a broken heart. "I've never really gotten over it," he said. "It was one of the worst times of my life."
Justin Theroux, 2011 to present
She met Theroux after she had been rumored to have been dating her "Bounty Hunter" co-star Gerard Butler. She has dismissed claims anything went on with Theroux on the set of "Wanderlust," as he was with his former girlfriend, fashion stylist and costume designer Heidi Bivens. But by May 2011, it was clear that these two were on their way to getting engaged after he and Bivens went their separate ways.
Months before he asked her to marry him, Aniston gushed about his acting abilities to MTV News. "What I think is so awesome about Justin is that he really just disappears," she said. "He sort of morphs into things, into characters and also has a leading-man quality, which I think is beautiful. He's just great."
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