There's the "Mr. and Mrs. Smith" affair, the "Friends" coupling,
and the "Se7en" romance. But not everybody's feeling the love!
Here's what Brad Pitt's exes really think of their hunky former fling.
Kim Hubbard is believed to be Brad Pitt's first ever girlfriend,
with the pair having dated in high school as young teens. In 2014, Hubbard told the Daily
Mail that the two would sometimes go ice skating and attend sporting events together, adding,
"I think everybody knew he would be successful in whatever he would do. […] He just had a
personality that attracted people, he had leadership skills, and he was sweet and kind."
Hubbard went on to marry baseball-player-turned-coach
Howard Bell. And as for whether she regrets not staying with Pitt, she says,
"In my dreams! But no, I've never really thought
about it. I do know that my story went a different way."
Back in the '80s, Pitt dated singer Sinitta, who is best known for her 1985 hit "So Macho."
According to her, the pair had a hot 'n' heavy romance that never veered into serious
territory. She recalled to Absolute Radio that on their first date, the pair ended
up rolling around on the floor of the VIP box during a show at the Royal Albert Hall.
"I like a boy who knows how to — who prepared
to roll around on the floor in the VIP box, you know."
But Sinitta claims she never
had any interest in her ex's budding A-list status. As she explained to New Magazine,
"To be honest, he was just a jobbing actor. He was in 'Dallas' for a bit,
but I never watched that, so I didn't know or care if he was a good actor or not,
he was just a really cute, fun guy who I fancied."
The two parted ways in 1988, but Sinitta is still spilling the deets on their fling,
revealing on "I'm A Celebrity" in 2011,
"He was beautiful with the most amazing body."
Scream queen Jill Schoelen starred in classic horror fare like "The Stepfather"
and "Popcorn." And in 1988, she met Pitt while they shot the flick "Cutting Class."
"Not until your grades improve."
Unlike his previous casual flings, Pitt's relationship with Schoelen
was very serious and the pair even got engaged. Radar published a collection
of love letters that Pitt apparently wrote to his then-fiancée, with the star reportedly declaring,
"I can't stop thinking about you. I don't feel complete without you next to me."
For her part, Schoelen had nothing but praise for her famous ex, telling the outlet,
"Brad wrote me one of the most beautiful poems a man can write
a woman. I thought he was so deep and soulful."
Still, the couple's engagement was called off in 1989. Chatting with The Sun in 2011,
Pitt claimed he was heartbroken when Schoelen left him for a film director.
The actor had supposedly spent all but $200 of his life savings to fly
to Hungary to see his fiancée where she was filming, only for her to promptly dump him.
Pitt quickly moved on to actor and voice talent Elizabeth "E.G." Daily. Appearing in Pitt's
"E! True Hollywood Story," Daily reflected fondly on her former boyfriend, recalling,
"He was a very deep-souled guy. He was very up and coming. I just knew that he was super cute."
Years later, in 2016, as Pitt was facing accusations of domestic violence following
an alleged physical altercation with his young son Maddox and then-wife Angelina Jolie,
Daily spoke out in his defense. Claiming that Pitt couldn't possibly be guilty
of the claims levied against him, she told the Daily Mail,
"Brad isn't an aggressive man. Not at all. I know Brad doesn't behave in that kind of manner."
Though she admitted that she hadn't spent time with Pitt in many years and didn't
know the precise circumstances of the allegations, Daily insisted that he had
previously behaved in the opposite manner than that of which he had been accused. She said,
"He's very laid back, very earthy. He was never someone that was super Hollywood,
he was a very calm and gentle guy."
Pitt began dating actor Juliette Lewis when she was reportedly just 16. He was a
full decade older. In 1993, she revealed that she met Pitt when they filmed the
TV movie "Too Young to Die?" three years earlier. And as she told the L.A. Times,
"I already liked him as an actor, plus you gotta respect somebody who's in the same field as you."
"We're gonna howl at the moon, g–damnit. [Howls] Yeah. Just like that."
At the time, they had just wrapped their second project together,
"Kalifornia." But the pair parted ways soon after. Still, Lewis admitted that
she only has fond memories of her former co-star, whom she said she genuinely
loved. She explained to The Guardian, "He's not in my universe at all now. It
seems like a high-school relationship because now he's a very famous person."
Although initial reports suggested that the couple dated for three years, Lewis says that
they were actually together for four years. But she also admitted that the media attention she
and Pitt generated had a costly negative effect on their relationship. Chatting with the Daily
Mail in 2010, she confirmed that she was still in high school when she dated the star, adding,
"I was a teenager at the time. It's a lifetime away. I was in
my high-school years and it was a wonderful, loving relationship."
Pitt and a then 22 year old Gwyneth Paltrow became a thing when they
made "Se7en," in 1995. Chatting to the L.A. Times in 1996, Paltrow admitted,
"When Brad and I met, he says, it was obvious that he liked me and that I was an idiot. But I had no
idea. I thought he was just really friendly. And then I started getting a crush on him."
The pair got engaged that year. During a Goop interview, she recalled how her father,
the late director Bruce Paltrow, cried with joy when the couple announced their engagement,
since he considered Pitt his second son. Although the duo split soon after,
Paltrow told ET Canada that she has nothing but love for her former fiancé,
with whom she had a happy relationship. Reportedly, the pair remain great friends.
Sadly, as loving as their romance may have been, it was also blighted by trauma. In 2017,
Paltrow opened up about being sexually harassed by disgraced film producer Harvey
Weinstein. Speaking to Howard Stern in 2018, she revealed that she told
Pitt about Weinstein's alleged inappropriate advances, and he then confronted Weinstein,
telling him to leave his girlfriend alone otherwise he would kill him.
"He leveraged his fame and power to protect me at a time when I didn't have fame or power yet."
From that point on, Paltrow noted, Weinstein kept his distance.
Undoubtedly one of the biggest celeb power couples of the turn of the millennium,
Pitt and Jennifer Aniston tied the knot in 2000 and quickly became a tabloid staple.
But Aniston was always hesitant to gush over
her husband. In a 2003 interview with W magazine, she explained,
"Is he the love of my life? I think you're always sort of wondering,
'Are you the love of my life?' I mean, I don't know, I've never been someone who says,
'He's the love of my life.' He's certainly a big love in my life."
In 2005, Aniston filed for divorce, citing irreconcilable differences.
But also at the time, there was considerable speculation as to
whether Pitt had embarked on an affair with his "Mr. and Mrs. Smith" co-star,
Angelina Jolie. Aniston admitted that she was devastated by the divorce, but
she still acknowledged that Pitt hadn't set out to purposely hurt her. As she told Vanity Fair,
"Brad is not mean-spirited. He would never intentionally try
to rub something in my face. There's a sensitivity chip that's missing."
But it appears that any lingering bad blood between the exes has since dissipated,
with Aniston telling Howard Stern in 2021 that she and Pitt are good friends.
"I'll run into Jen. She's a good friend."
Angelina Jolie claims that neither she nor Pitt were looking for a relationship when they met on
the set of "Mr. and Mrs. Smith" in 2003. But in time, she found herself falling for her co-star,
with whom she went public in 2005. As she told Vogue two year later in 2007,
"We push each other to be better. Even if it's just a better bike rider or a better
pilot. He's somebody I admire based on the way he lives his life. And that's why I'm with him."
The couple welcomed six children but didn't tie the knot until 2014. They had previously stated
that they wouldn't get married until same-sex marriage was legalized in the U.S. In 2013,
Jolie wrote an essay for The New York Times, in which she revealed she had
undergone a preventative double mastectomy due to a genetic predisposition for breast
cancer. And she praised her husband for supporting her throughout her journey.
"You approached our marriage like a job, something to be reconned, planned and executed."
"And you avoided it."
But ever since the couple's split in 2016, Jolie has seemingly reassessed her thoughts on Pitt. She
hinted at the pair's relationship being troubled for a long time, telling The Guardian in 2021,
"There's a lot I can't say. I think at the end of the day, even if you and a few people you
love are the only people who know what you've suffered, you come to be at peace with that."
If you or anyone you know has been a victim of sexual assault,
help is available. Visit the Rape, Abuse & Incest National Network
website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).