Her First Love

In an interview with Rolling Stone, Aniston revealed her first love: Daniel McDonald, an eventual Tony nominee whom she dated for five years.

“When we broke up, he moved to New York and started doing great. Just before Friends, we broke up,” she said. She then added, “He’s just wonderful. A dear friend.”

And Aniston opened up about her relationship with McDonald, who died of a brain tumor in 2007, in a 2015 interview with The New York Times, saying, “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.”

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Brief Time With Bueller

Before landing the role of Rachel on Friends, Aniston played Jeanine Bueller, Ferris’ little sister, in the failed TV series based on the iconic movie, Ferris Bueller’s Day Off.

During the show’s brief run, Aniston dated her co-star Charlie Schlatter, who played Ferris aka her on-screen brother.

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Rocker Phase

Aniston briefly dated the Counting Crows lead singer in 1995, just as Friends was taking off. And two years later, Duritz went on to date her BFF and co-star, Courteney Cox.

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Tate Donovan Comes In

Before he was known as Jimmy Cooper on The O.C., Donovan was probably best known as Aniston’s first fiancée, who was her first serious boyfriend after becoming a household name on Friends.

“He’s so real, so honest, so kind and considerate,” Aniston gushed to People of her then-boyfriend, whom she started dating in 1995 after being set up by mutual friends. “He’s all these things meshed into one perfect guy.”

For Donovan, who had previously dated Sandra Bullock for four years, he admitted he “didn’t know who she was…I’d never seen Friends.”

He was initially hesitant about dating another high-profile star after his romance with Bullock, and even called off their romance after just one month because “literally, our second date, there were video cameras everywhere, and I was like, ‘I’m out of here.'” Three weeks later, he changed his mind, and by their first anniversary, the couple had exchanged Irish commitment rings. He surprised her with a puppy, Enzo, for Valentine’s Day.

While some speculated an engagement was inevitable, Aniston told People, “There’s nothing to report. You have to take more time to get to know someone.”

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The One With the Awkward Break-Up

After almost three years together and once considering marriage, the couple decided to call it quits. The only problem? Donovan had been cast on Friends as Rachel’s new boyfriend, Joshua. Awkward!

“I was just happy to be on the team. The only bummer was Jennifer and I were breaking up at the time,” Donovan recalled in an interview with US Weekly. “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.”

Rachel and Joshua only ended up dating for six episodes, due in large part to their break-up IRL.

“It was just six episodes. I mean, only because we were breaking up. We were like, ‘Hey, can we not keep doing this? ‘Cause this is really painful and tough,'” he explained. “The people that know that we dated think that we met on Friends. But in fact we had dated for two years before then, and it was over by the time we were on Friends together.”

While reports surfaced that their break-up was due to Donovan’s jealousy over Aniston’s career, she shot down that rumor in a 1999 chat with Rolling Stone.

“That wasn’t actually why we broke up. But because we didn’t give the press anything, they made it up,” she said. “Tate’s and my breakup had nothing to do with ego battles, wanting babies, not wanting marriage — all that stuff. None of it was accurate.”

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The Origins of Hollywood’s Golden Couple

And then came “Brad and Jen,” one of the most notorious celebrity couples of all-time.

The well-coiffed couple first met in 1994 as their managers were friends. A few years later, both fresh off break-ups (Aniston with Donovan, Pitt with Gwyneth Paltrow), they were set up on a date by their managers in 1998.

Given their status as America’s ultimate heartthrob and sweetheart, the couple initially went to great lengths to keep their romance private.

“I’m not withholding, just preserving something that’s mine,” Aniston once told Rolling Stone in 1999 when asked about her relationship with Pitt. “To talk about a relationship trivializes something that’s nobody’s business.”

She finally relented, and simply said, “I’ll just tell you that this is the happiest time of my life. I’m not saying why, it’s for a lot of reasons: work, love, family, just life—all of it.”

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The $1 Million Wedding

However, Aniston was much more willing to dish on her man a few years later, divulging details to Rolling Stone.

Because he was, you know, Brad Pitt, Aniston revealed in a 2001 interview that some of her friends were initially hesitant about their relationship but soon became “supportive” after meeting the actor.

“At first they’re like, ‘I hope he’s not an asshole, some conceited f–k or whatever.’ But you get past that in five minutes,” she said, “Which is a real tribute to who he is. He just disarms you immediately. But, I mean, nobody went, ‘Dude. Brad Pitt!’ and gave me a thumbs up and a wink. They were just happy for me.”

After less than a year of dating, Pitt proposed to Aniston, and after two years together, they said “I do” on July 29, 2000, in Malibu. Their lavish wedding, which cost a cool $1 million and had impressive security measures in place, was attended by her Friends co-stars (except for Matt LeBlanc, who was filming a movie), Cameron Diaz, Salma Hayek and more A-listers. She promised to always make his “favorite banana milk shake.” He agreed to “split the difference on the thermostat.” There were actual fireworks.

“I had those typical jitters the day before my wedding,” Aniston told Rolling Stone of the big day, “but 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.”

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The Announcement

Five years later, the split that changed pop culture happened, with Aniston and Pitt announcing their separation on January 7, 2005, shortly after taking a New Year’s trip to Anguilla together.

“We would like to announce that after seven years together we have decided to formally separate. For those who follow these sorts of things, we would like to explain that our separation is not the result of any of the speculation reported by the tabloid media. This decision is the result of much thoughtful consideration,” the pair said in a joint statement. “We happily remain committed and caring friends with great love and admiration for one another. We ask in advance for your kindness and sensitivity in the coming months.”

The news came after months of split rumors…and whispers-turned-headlines of Pitt and his Mr. & Mrs. Smith co-star Angelina Jolie growing closer.

And that is how the most infamous love triangle in Hollywood history started.

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The Interview

Six months later, Aniston gave her first post-divorce interview, and it was an iconic one.

In her candid interview with Vanity Fair, Aniston didn’t hold back. She weighed in on the photos of Pitt and Jolie on the beach together: “Who would deal with that and say, ‘Isn’t that sweet! That looks like fun!’ But s— happens. You joke and say, ‘What doesn’t kill you makes you stronger.'”

Pitt and Jolie’s infamous photoshoot, depicting them as a family, which Pitt came up with the concept for? “There’s a sensitivity chip missing.” Pitt’s (at the time) new bleached ‘do? ”

As for rumors that Pitt left her because she didn’t want to start a family? “A man divorcing would never be accused of choosing career over children,” she said. “That really pissed me off. I’ve never in my life said I didn’t want to have children. I did and I do and I will!”

In the Vanity Fair profile, Aniston did admit, “I love Brad; I really love him. I will love him for the rest of my life,.” And she went on to say, “We spent seven very intense years together…a beautiful, complicated relationship…I really do hope that someday we can be friends again.”

And she revealed in a 2008 Vogue interview that they eventually talked on the phone and “had a long, long conversation…and said a lot of things, and ever since we’ve been unbelievably warm and respectful of each other.” (Still, she went on to infamously call Jolie “uncool” for comments she made about the beginning of her relationship with Pitt.)

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First Post-Pitt Relationship: Vince Vaughn

Aniston and The Wedding Crashers star immediately had headlines speculating they were a couple as they filmed their rom-com-gone-wrong The Break-Up soon after her divorce from Pitt. (Yes, she was aware of the irony of the movie’s title.)

Aniston initially denied the rumors, telling Vanity Fair, “I adore Vince Vaughn, but I’m not going out with Vince Vaughn, I barely know the guy. We’ve exchanged a wine-and-cheese basket for the start of the movie, and we’ve gone out to dinner with the director and other people. We’ve got to get to know each other.”

But eventually, it came out that they were dating IRL, though they tried very hard to keep their romance private.

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IRL Break-Up

The couple split in December 2006 after less than a year of dating, with their reps saying they decided to break up during her trip to London to visit him on the set of Fred Claus. And in a joint statement, they said they would “continue to be good friends.”

A few years later, Aniston looked back on their time together fondly in an interview with Vogue, calling Vaughn her “defibrillator,” explaining he “literally” brought her “back to life” when they began dating.

She added, “My first gasp of air was a big laugh! It was great. I love him. He’s a bull in a china shop. He was lovely and fun and perfect for the time we had together. And I needed that. And it sort of ran its course.”

As for Vaughn, who is now married to Kyla Webber (and has two children with her), he opened up about their romance in a 2015 Playboy interview, admitting the constant attention on their relationship got to him.

“You know, she’s great,” Vaughn said. “For me personally—and I think most well-known actors who are together feel this way—I never enjoyed the paparazzi side of it.”

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AP Photo/Lisa Rose

John Mayer, Round 1

While she “barely knew” his music before dating him, Aniston and the playboy musician began dating in February 2008 after meeting at an Oscars party “and then we ran into each other a week later, and that was that,” Aniston revealed to Vogue.

She joined him when he was touring in England. They took a paparazzi-d vacation to Miami. She helped him celebrate his 31st birthday. Given his dating history (Jessica Simpson, Jennifer Love Hewitt, etc.) and her, well, being Jennifer Aniston, the tabloids documented their every move.

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Split With John Mayer, Round 1

Their first split was a very public one, as Mayer was (unfortunately) on one of his TMI press kicks, and he infamously held an impromptu press conference outside of his gym in NYC after breaking up with Aniston.

“I’m the a—hole,” he said. “I burned the American flag. I basically murdered an ideal.”

In her Vogue profile, Aniston sort of defended Mayer, blaming it on his inexperience with handling life in the spotlight.

“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,” she told the publication. “Trust me, you’ll never see that happen again from that man. And it doesn’t take away from the fact that he is a wonderful guy. We care about each other. It’s funny when you hit a place in a relationship and you both realize, We maybe need to do something else, but you still really, really love each other. 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.”

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John Mayer, Round 2

Despite the first breakup and Mayer’s bizarre handling of it, Aniston surprised many when she attended the 2009 Oscars with Mayer on her arm, marking their first official red carpet appearance together as a couple.

Backstage, Aniston told Gayle King, who was interviewing them for her BFF Oprah Winfrey’s show, that she was “very happy,” and the couple was later spotted getting quite cozy at the Vanity Fair party following the ceremony.

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Split With John Mayer, Round 2

Alas, just one month later, the couple had reportedly called it quits, with a source telling E! News at the time that “he broke up with her when she got back from her European tour,” during which she was promoting Marley & Me.

But in 2010, after Mayer took a mini-break from public speaking and dating, he reflected on his romance with Aniston, admitting to Rolling Stone that he had “never really gotten over” their split. “It was one of the worst times of my life.”

And in 2012, he admitted he regretted his handling of their break-up.

“I was going through a time in my life where I didn’t really want to share what was going on, but I didn’t want to be boring,” he said on the NPR show All Things Considered.

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Jen and Justin

Aniston met her second husband Justin Theroux on the set of Tropic Thunder, the movie he wrote, in 2007. Looking back on their first meeting years later, Aniston admitted she thought he was the “nicest person in the world” but also could possibly be “a serial killer” because of his biker-style. But the two didn’t begin dating until 2010, when they reconnected on the set of Wanderlust, in which they both starred.

And in August of 2012, the couple got engaged on Theroux’s birthday, popping the question with an 8-carat ring. And they seemed happy and content, no matter how hard the tabloids tried to push the “Poor Jen” narrative that had followed her ever since her divorce from Pitt.

“How many times can I be out there in the world, enjoying my life, and yet the narrative is ‘Poor, Sorry, Sad in Love Jen’…whatever the stupid headline is,” the actress shared with Harper’s Bazaar during her engagement. “It’s almost impossible to get bored with one another. We’ve tried so hard! And even that’s interesting because his eyes are so pretty, but we can entertain ourselves and talk about endless things, which is pretty great.”

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Second Secret Wedding

Three years later, the couple got married in a super-secret ceremony in their backyard, even telling guests it was a party for Theroux’s birthday. Some famous faces that received an invite were her Friends’ BFFs Courteney Cox and Lisa Kudrow, Emily Blunt and John Krasinski, and Ellen Degeneres and Portia de Rossi, with Jimmy Kimmel officiating the ceremony, Sia performing and Howard Stern delivering a memorable toast.

No photos were ever released from the intimate day, but Justin’s best man/comedian Amy Sedaris said it was “perfect. Everyone was dressed like a bunch of woodland creatures.”

After their wedding, the couple invited some of their friends, including Cox and Chelsea Handler, on their honeymoon to Bora Bora.

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The Split

After less than three years of marriage, Aniston and Theroux announced their shocking separation in February 2018, just days after she was spotted celebrating her 49th birthday with friends (and sans husband) in Mexico.

“In an effort to reduce any further speculation, we have decided to announce our separation. 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,” the couple said in a joint statement to E! News. “Normally we would do this privately, but given that the gossip industry cannot resist an opportunity to speculate and invent, we wanted to convey the truth directly. Whatever else is printed about us that is not directly from us, is someone else’s fictional narrative. Above all, we are determined to maintain the deep respect and love that we have for one another.”

In her first post-split interview with InStyle, Aniston admitted the never-ending tabloid stories about her love life can be “pretty crazy,” and addressed the biggest misconception about her head-on.

“The misconceptions are ‘Jen can’t keep a man,’ and ‘Jen refuses to have a baby because she’s selfish and committed to her career.’ Or that I’m sad and heartbroken. First, with all due respect, I’m not heartbroken. And second, those are reckless assumptions,” she said. “No one knows what’s going on behind closed doors. No one considers how sensitive that might be for my partner and me. They don’t know what I’ve been through medically or emotionally. There is a pressure on women to be mothers, and if they are not, then they’re deemed damaged goods. Maybe my purpose on this planet isn’t to procreate. Maybe I have other things I’m supposed to do?”

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Her Outlook on Marriage Now

Despite her two divorces, Aniston doesn’t look at either of her high-profile marriages as failures.

“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,” she explained to Elle. “Sure, there were bumps, and not every moment felt fantastic, obviously, but at the end of it, this is our one life and I would not stay in a situation out of fear. Fear of being alone. Fear of not being able to survive. To stay in a marriage based on fear feels like you’re doing your one life a disservice. When the work has been put in and it doesn’t seem that there’s an option of it working, that’s okay. That’s not a failure. We have these clichés around all of this that need to be reworked and retooled, you know? Because it’s very narrow-minded thinking.”

As for her outlook on dating and possibly becoming a mother, Aniston said, “Who knows what the future holds in terms of a child and a partnership—how that child comes in…or doesn’t? And now with science and miracles, we can do things at different times than we used to be able to.”