Jen's destined to be haunted by fake Prego pics forever,
but when it comes to her exes,
it's a legit trail of broken hearts,
besties, or nemesis. 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 cancelled 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 Slaughter, 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 and Order,
and he was nominated for a Tony Award for his
role in Broadway 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,
think it didn't last very long,
but she's a nice girl.
Do you know something? Do you know something?
According to Us Weekly, Duritz claimed that T 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 Courtney 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 OC 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 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. We were 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 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 2 greatest Enemies, Ross,
Rachel Green 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.
and Missus 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 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 of of
of her year, it was Vince Vaughn to the rescue
after Aniston and Pitts high profile split.
The two actress began a relationship in the summer of
2005 while filming their comedy The Breakup.
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. Von 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 Mayor gave a sort of DIY press
conference outside his New York gym to discuss their initial
breakup,
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 Mayor along as her date to the
2009 Oscars. However, it wasn't long before they split again.
During an interview with Rolling Stone in
2010, Mayor 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 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.
Well, if we need each other,
I think you're there for each other.
There, long time 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 Thoreau Co wrote,
they didn't strike up a romance until
2011 when they worked together in Wanderlust.
It wasn't long before Thoreau 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 seems like the real deal.
Which then led to extreme shock when news broke of
the couple split in February
2018. However, like many of her previous relationships,
the two remained friendly. Thoreau first spoke out about their
split with The New York Times sharing.
The good news is that was probably the most gentle
separation and 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 the wounds in
2021. Thoreau 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 thank the same for her.