Jen's destined to be haunted by fake preggo pics forever.
But when it comes to her exes, it's a legit trail of broken hearts.
Besties or nemeses, here's what her old flames really think of her.
Four years before Jennifer Aniston landed the coveted role of Rachel Green on "Friends,"
she starred in the 1990 TV adaptation of the film "Ferris Bueller's Day Off."
Actor Charlie Schlatter starred as Ferris, while Aniston played his older sister.
"Ferris Bueller" the show was canceled after one season, but it wasn't until 2014 that
fans learned of the short-lived romance, with GQ writer Jim Nelson noting,
"GQ can exclusively report that everyone on set thought she was hot, including Schlatter,
with whom she had a brief, torrid romance."
Neither party ever confirmed or denied a relationship.
In 2019, when Aniston was shown an old cast photo and asked if she'd be up for a reunion,
she told Access Hollywood,
"Absolute no.
I don't even think half of those actors are even still in the business."
During a 1999 interview with Rolling Stone, Aniston shared that her, quote, "first real,
mature relationship" was with actor Daniel McDonald, whom she dated from 1990 to 1995.
McDonald guest-starred on "Sex and the City" and "Law & Order," and he was nominated for
a Tony Award for his role in Broadway's "Steel Pier."
Aniston told The New York Times in 2015,
"He was my first love — five years we were together.
He would have been the one.
But I was 25, and I was stupid."
McDonald died in 2007 from brain cancer at the age of 46.
At the time, he was happily married with two children.
It's unclear how long Aniston dated Counting Crows' lead singer Adam Duritz, but their
short-lived relationship occurred sometime in 1995.
Speaking with Entertainment Tonight in 2021, Duritz recalled first meeting Aniston at the
famous Los Angeles music venue The Viper Room.
In addition, the singer revealed how he and Aniston were awkwardly set up, sharing with Vice,
"A bunch of my friends lied to me and told me she had a crush on me.
Those same friends lied to her and told her I had a crush on her.
I honestly had no idea who she was, I had been on the road during 'Friends.'
I had never seen it, I don't think.
It didn't last very long, but she's a nice girl."
"Do you know something?"
According to Us Weekly, Duritz claimed that he and Aniston didn't even make it to third
base, admitting that they were never intimate during their relationship.
As ET noted, Duritz went on to date Aniston's "Friends" co-star Courteney Cox in 1997, who
also appeared in the Counting Crows music video for "A Long December."
In an interview with Men's Health in 2014, he simply shared,
"They were nice girls and I went out with them and that was that."
"The O.C." star Tate Donovan was set up with Aniston by mutual friends in 1995 after he had previously
dated actor Sandra Bullock.
Aniston gushed to People in 1997,
"He's so real, so honest, so funny, so kind and considerate.
He's all these things meshed into one perfect guy."
Donovan even talked about the possibility of marriage, telling the outlet,
"I definitely want to get married; she definitely wants to get married.
There are no proposals or anything, not yet, but we definitely think about it."
Though there are conflicting reports on whether Donovan ever popped the question, the couple
split in 1998.
That same year, he landed a recurring role on "Friends," playing Rachel Green's crush,
Joshua, for six episodes.
He recalled the experience to Us Weekly, remembering,
"I was just happy to be on the team.
The only bummer was Jennifer and I were breaking up at the time.
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."
"I remember just getting back to my dressing room and just weeping."
Looking back, Donovan admitted that though the entire "Friends" cast was great, he still
felt like he was, quote, "sort of dying inside" throughout his time working on the show.
In 2005, he married Corinne Kingsbury, but the couple divorced three years later.
The late '90s gave us Hollywood's most talked about couple: Jennifer Aniston and Brad Pitt.
The duo began dating in 1998 and tied the knot two years later.
Pitt even joined his wife on "Friends," starring in a Thanksgiving episode as a character who
despised Rachel Green.
"My two greatest enemies, Ross; Rachel Greene and complex carbohydrates."
Just as "Friends" was wrapping up in 2004, Aniston appeared to be ready to start a family
with Pitt when she told The Guardian,
"It's time.
It's time.
You know, I think you can work with a baby, I think you can work pregnant, I think you
can do it all."
But the power couple shocked the world with their split in early 2005.
Rumors swirled that Pitt had strayed and cheated with his "Mr. & Mrs. Smith" co-star Angelina
Jolie, with whom he would end up dating shortly after his divorce.
In 2007, Pitt told V magazine that he and Aniston are still very close friends despite
their separation.
But his 2011 interview with Parade had fans questioning his marriage to Aniston when he
revealed that his life had been a little boring.
The actor clarified his statements, via Reuters, saying,
"The point I was trying to make is not that Jen was dull, but that I was dull to myself
— and that, I am responsible for."
In 2020, all seemed to be well between the exes when they were spotted reuniting at the SAG Awards.
But sadly for fans of this former couple, it didn't mean these two were rekindling their romance.
"The second, the second most important reunion of her year."
It was Vince Vaughn to the rescue after Aniston and Pitt's high-profile split.
The two actors began a relationship in the summer of 2005 while filming their comedy
"The Break-Up."
At the time, Vaughn told People,
"She's awesome.
She has just a wonderful warmth and likability about her."
But by the end of 2006, the two had called it quits.
Ever since, the pair has continued to say nothing but good things about each other.
In 2008, Aniston told Vogue,
"He literally brought me back to life.
My first gasp of air was a big laugh!
It was great.
I love him […] He was lovely and fun and perfect for the time we had together.
And I needed that."
Vaughn revealed how overwhelming it was to deal with the media coverage of their romance,
telling Playboy in 2015,
"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."
After Vaughn, of course, there was John Mayer.
Aniston and the singer dated on and off for about a year after meeting at an Oscars after-party
in early 2008.
They split in August of that year, at which point Mayer gave a sort of DIY press conference
outside his New York gym to discuss their initial break up.
He told TMZ,
"There's no lying, there's no cheating, there's no nothing.
People are different, people have different chemistry."
The former couple gave it another go, with Aniston bringing Mayer along as her date to
the 2009 Oscars.
However, it wasn't long before they spit again.
During an interview with Rolling Stone in 2010, Mayer shared that the split was one
of the hardest times he had ever been through, recalling,
"I have this weird feeling, a pride thing, for the people I've had relationships with.
What would I be saying to Jen, who I think is f—ing fantastic, if I said to her, 'I
don't dislike you.
In fact, I like you extremely well.
But I have to back out of this because it doesn't arc over the horizon.
This is not where I see myself for the rest of my life, this is not my ideal destiny.'"
That same year, Mayer's controversial Playboy interview came out, during which the singer
confessed to still loving Aniston.
But, he appeared to take a dig at their age gap when he said,
"I'll always be sorry that it didn't last.
In some ways I wish I could be with her.
But I can't change the fact that I need to be 32."
"If we need each other, I think,"
"You’re there for each other"
"We know we're there."
Longtime fans of Aniston were over the moon to see the actor find love again with Justin
Theroux.
Though they first met on the set of "Tropic Thunder" in 2007, which Theroux co-wrote,
they didn't strike up a romance until 2011, when they worked together in "Wanderlust."
It wasn't long before Theroux proposed to the star in 2012, and the two wed in a top-secret
ceremony at their California home in 2015.
"Linda?
I think you just met Linda."
It seemed like the real deal, which then led to extreme shock when news broke of the couple's
split in February 2018.
However, like many of her previous relationships, the two remained friendly.
Theroux first spoke out about their split with The New York Times, sharing,
"The good news is that was probably the most […] gentle separation, in that there was
no animosity.
[…] It was heartbreaking, only in the sense that the friendship would not be the same,
as far as just the day to day."
But it appears that time heals at least some of the wounds.
In 2021, Theroux shared with Esquire that the pair even Facetime on occasion, adding,
"I'm sincere when I say that I cherish our friendship.
It would be a loss if we weren't in contact, for me personally.
And I'd like to think the same for her."