The Truth About Jennifer Aniston's Famous Exes

Jennifer Aniston's love life has been under constant scrutiny since she first debuted on the small screen on NBC's "Friends." The gorgeous actress quickly found herself matched up with any male she happened to become friendly with, whether or not their affection for one another translated into a romantic entanglement. The interest in Aniston's love life hit a fever pitch as the show grew in popularity, and Aniston became one of Hollywood's "It" girls.

Even after two marriages and divorces and a handful of high-profile relationships, Aniston reportedly has not stopped looking for a profound romantic union. "She hasn't given up on love," a source told Us Weekly of the actress in 2019. Aniston has always made it very clear that she does not need a man in her life to feel fulfilled. However, when she does find a man she can connect with on a spiritual level, she gives her all to the relationship. "I never liked 'Sex and the City,' the kind of thing where women only feel empowered once they find The Man," she admitted to Vogue in 2008. "It is just not up my alley. I don't believe in it. There is nothing you can control about love."

So what is the truth about Jennifer Aniston's famous list of exes? What quality did they have that attracted them to her? There's a lot you don't know about the romantic life of your favorite "Friends" actress.

Aniston's first love was actor Daniel McDonald. The couple dated for four years, from 1990 to 1994, shortly before Aniston got her big break on "Friends. " The actress said to The New York Times, "He was my first love — five years we were together. He would have been the one. But I was 25, and I was stupid. He must have sent me Justin [Theroux] to make up for it all."

Daniel was an actor who appeared on the television series "Sex and the City," "All My Children," and "Law & Order. He also starred in the stage productions of "Steel Pier" and "High Society." He died at the age of 46 in 2007. His widow, Mujah Maraini-Melehi, acknowledged her husband and Aniston's long relationship. She said in an interview after McDonald's death to Us Weekly, "I am sorry that Jennifer did not realize the treasure that was Daniel when she had the chance, long before he and I met and long before he died."

The Counting Crows lead singer helped heal the actress' broken heart from McDonald. With his dreadlocks and soulful voice, Adam Duritz was Aniston's leading man in 1995. They kept their brief relationship quiet. Aniston was riding high on "Friends" success, and Duritz's band Counting Crows had just won two Grammys the year prior, making them a power couple early in their respective careers.

"Jen and Adam had become friends, and they were hanging out there," photographer Randall Slavin said in an interview with InStyle of a home shared by actress Samantha Mathis, an old friend of Adam's, and Tracy Falco.  "Friends had just exploded and was massive, and Adam was in the biggest band in the country, and his record was blowing up, so they were the biggest power couple." Of Aniston, Slavin said, "Jennifer was exactly like she's always been — sweet, approachable, and completely taking everything in her stride. When I run into her now, she's still very sweet."

Tate Donovan was the first boyfriend that the "Friends" star hit the gossip mags' front pages with. They met through mutual acquaintances, and their relationship was a strong one, lasting for three years from 1995 through 1998. At the time of their meeting, Donovan claimed that he did not know who Aniston was, even though at that point "Friends" was at the top of the rating heap for NBC. "Our second date, there were video cameras everywhere, and I was like, 'I'm out of here,'" Donovan said (via E! News). They would eventually split up and reunite less than a month later by exchanging Irish commitment rings on their first anniversary as a couple.

After almost three years together, the couple decided to call it quits. The problem was that Donovan was hired to play Rachel's new boyfriend, Joshua. "I was just happy to be on the team. The only bummer was Jennifer and I were breaking up at the time," said the actor to Us Weekly. "And, so that was tricky to sort of act and act like we were 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."

Brad Pitt and Aniston met in 1994 via their managers. "He was just this sweet guy from Missouri, you know?" she said (via Rolling Stone). "A normal guy." However, they would not start dating until 1998 and kept their relationship under wraps. Aniston and Pitt put a ring on it in November 1999, crashing a Sting concert in New York City and showing off her bling on stage. Pitt reportedly spent $500,000 on the ring, which had a center diamond and a winding coil of smaller diamonds encircling the central stone (via Brides). In July of 2000, the couple wed in a luxurious Malibu event where Jennifer wore a glass-beaded, low back wedding gown by Lawrence Steele as she walked down the aisle.

"I had those typical jitters the day before my wedding," said Aniston (via Rolling Stone). "[B]ut the day of, I was just excited in a good way. The nice thing about weddings now is it's not just a chick thing. It's a team effort. The stereotype used to be men grumbling, like, 'Why are you making me do this?' There's nothing more moving than seeing a man cry at his own wedding." The couple would split in January of 2005 after rumors that he had an affair with Angelina Jolie during the filming of "Mr. and Mrs. Smith." Their divorce would be finalized in October 2005, and Pitt would go on to marry Jolie and, together, parent six children.

The actress dated funnyman Vince Vaughn shortly after breaking up with Pitt. The two co-starred in the film "The Break-Up." Their year-long romance was easy and fun, although highly scrutinized by the paparazzi. Aniston continued to work on "Friends," and Vaughn became a fixture in her life not only a professional manner but as a person she could confide in.

"She's great," said Vaughn of Aniston to the HuffPost. "For me personally — and I think most well-known actors who are together feel this way — I never enjoyed the paparazzi side of it. 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. I think lying low and not talking about it put me in a good position later because I just wasn't part of anything."

Musician John Mayer met Aniston at an Oscars party. They began dating in 2008, and their on-again, off-again romance would last one year. She spoke of her union with Mayer to Vogue, sharing that she didn't even know his music when they initially met. "And then we ran into each other a week later, and that was that." The press followed their every move due to Mayer's reputation as a womanizer and the fact that he was nine years younger than the actress when they began dating. She claimed that their relationship "isn't designed. Love just shows up, and you go, 'Oh, wow, this is going to be a hayride and a half.'"

Mayer famously lost his cool with paparazzi in New York City, telling them, via Vogue, "If you guys are going to...run every lie under the sun...have me as a man who ended a relationship." In response to Mayer's comment, Aniston would later say, "He had to put that out there that he broke up with me. And especially because it's me. It's not just some girl he's dating. I get it. We're human. But I feel seriously protective of him and us. It's painful. There was no malicious intent. I deeply, deeply care about him; we talk, we adore one another. And that's where it is."

Justin Theroux and Aniston met on the set of the comedy film "Tropic Thunder." Aniston was close friends with one of the movie's stars, Ben Stiller. Theroux co-wrote the screenplay and story for the 2008 comedy, which starred Stiller, Jack Black, and Robert Downey Jr. In 2012, they starred in the movie "Wanderlust." Jennifer kept her feelings for the writer and actor quiet, but admitted in an interview with InStyle, "Having experienced everything you don't want in a partner over time, it starts to narrow down to what you actually do want," she admitted. "As I get older, I realize what qualities are important in love and what suits me. And what I won't settle for."

In 2012, Theroux placed an eight-carat, emerald-cut solitaire diamond ring on Aniston's finger with an estimated value of $500,000 (via Brides). Aniston told The New York Times of her ring, "He rocked it up. It took me a while to get used to it. I'm not a diamond girl." They wed in 2015 in front of 70 guests, including Howard Stern, Orlando Bloom, "Friends" co-stars Lisa Kudrow and Courteney Cox (who served as maid of honor), Lake Bell, and Scott Campbell (Theroux's best man), Ellen DeGeneres, Chelsea Handler, Emily Blunt, John Krasinski, Tobey Maguire, and Jennifer Meyer, reported Brides. The guests were invited to the actor's birthday celebration and instead were treated to a surprise wedding ceremony where Jimmy Kimmel married the couple. The couple would split in 2018.