Inside the Many Loves of Brad Pitt, From Jennifer Aniston to Angelina Jolie and Beyond

Brad Pitt is playing the field.

Brad Pitt is known for his acting roles, sure, but also for being extremely handsome. Fans have been swooning over Pitt since his star-making turn in 1991’s Thelma & Louise. As a result, Brad Pitt’s love life has been in the spotlight almost as much as his movies.

Brad Pitt’s dating history is filled with some of the most beautiful women in the world. The father of six has had some very high-profile breakups that have taken place in the public eye. But, he’s also had some girlfriends that you may have forgotten about.

Here is all you need to know about Brad Pitt’s dating history.

Is Brad Pitt in a relationship?

At this time, it would appear that Brad Pitt is not in a committed relationship at this time. A source has told PEOPLE that the actor is currently casually dating, but nothing is serious. So… that means you still have hope, go shoot your shot!

Related: Brad Pitt Accuses Angelina Jolie of Harming Wine Brand

Who is Brad Pitt's new love?

Brad Pitt is not currently in a relationship, so he does not have a new love — unless you count his new $40 million bachelor pad on a cliffside in Carmel. Which … I think I do?

Who is Brad Pitt dating now?

In November 2022, Pitt was reportedly linked to Vampire Diaries star Paul Wesley's ex-wife Ines de Ramon. The pair were spotted hugging at a Bono concert, and sources later told PEOPLE that while their relationship isn't serious (yet), Pitt is "really into" jewelry designer de Ramon, 32, and that they'd been seeing one another for a few months. The pair reportedly rang in 2023 together during a vacation in Cabo San Lucas, Mexico.

Is Brad Pitt dating Emily Ratajkowski?

In late September 2022, Page Six reported that Pitt had been on a few dates with model Emily Ratajkowski following her split from estranged husband Sebastian Bear-McClard, but that it's not serious just yet. In early October 2022, sources confirmed to PEOPLE that Pitt and Ratajkowski were "having fun" but not in a committed relationship. It appeared to have fizzled out quickly, because by mid-November 2022, EmRata was seen getting cozy with Pete Davidson. Even Brad Pitt is no match for that BDE!

Is Jennifer Aniston in a relationship with Brad Pitt?

Jennifer Aniston is not currently in a relationship with Brad Pitt, to whom she was married from 2000 to 2005. The two sparked reconciliation rumors (and brought hope to their fans’ hearts) back in January 2020 when the former couple shared a sweet moment backstage at the SAG Awards. However, despite their fans’ wishes, it would appear the moment was just that and the exes remain apart.

Are Brad Pitt and Jennifer Aniston still together?

Brad Pitt and Jennifer Aniston have apparently not been together since their divorce in 2005. The two met in 1998 when they were set up on a blind date by their agent. The relationship ended due to Pitt’s alleged affair with future ex-wife Angelina Jolie on the set of 2005’s Mr. and Mrs. Smith.

Related: More Like Moneyball-er! Inside Brad Pitt's Massive Net Worth

How long did Brad and Jennifer date?

Brad Pitt and Jennifer Aniston first met in 1998 when they were set up on a date by their agent. They dated for two years before marrying in 2000. The pair reportedly split among rumors of infidelity when Brad Pitt was working with future ex-wife Angelina Jolie on 2005’s Mr. and Mrs. Smith. Aniston and Pitt were officially divorced in 2005. All in all, it appears the pair were together for around six to seven years.

How many wives has Brad Pitt had?

Brad Pitt has been married twice, once from 2000 to 2005, and again from 2014 to 2019 (though he and his second wife separated in 2016).

Related: Angelina Jolie and Brad Pitt Are Divorcing 'For the Health of the Family'

Who were Brad Pitt's wives?

Brad Pitt’s first wife was Jennifer Aniston, who he married in 2000 and divorced in 2005. Pitt’s marriage to Aniston reportedly ended due to an alleged affair he had with his second wife, Angelina Jolie, during the making of Mr. and Mrs. Smith.

Jolie and Pitt were together for almost a decade before marrying in 2014. Unfortunately, the relationship did not last as the two officially separated in 2016 and were declared legally single in 2019.

In October 2022, as a result of ongoing litigation between Pitt and Jolie over her former stake in their Miraval winery, court documents revealed that Jolie accused Pitt of physically abusing her and at least two of their children on a private plane from France to Los Angeles in September 2016. The incident is reportedly what led to their separation that month. In court documents, Jolie accused Pitt of asking her to sign a non-disclosure agreement barring her from speaking publicly about the alleged abuse she suffered during their relationship—and refusing to engage with her on a deal to sell the winery unless she complied.

How many biological children does Brad Pitt have?

Brad Pitt shares six children with his ex-wife Angelina Jolie. Three of these children are adopted, three are biological. These children are Maddox, Pax, Zahara, Shiloh, Vivenne and Knox.

Did Brad Pitt and Julia Roberts ever date?

Brad Pitt and Julia Roberts have been friends for many years, but the pair have never dated — despite rumors to the contrary. The duo have appeared in several movies together, including The Mexican, Ocean’s Eleven, and Ocean’s Twelve.

Did Geena Davis and Brad Pitt ever date?

While neither has officially confirmed the romance, it would appear that Geena Davis and Brad Pitt did indeed have a romance of sorts following their appearance together in 1991’s Thelma & Louise. Pitt’s former roommate Jason Priestley told The Hollywood Reporter that the two would meet up, keeping it secret at Davis’ request. Whatever the relationship was, it would appear it was short lived.

Did Brad Pitt and Gwyneth date?

Brad Pitt and Gwyneth Paltrow did date and even got engaged during their time together. The pair were in a much publicized relationship from 1994 to 1997, after meeting on the set of 1995’s Se7en. The duo have been able to form a friendship since their breakup and still say they have love for each other.

Of the relationship, Gwyneth has said, “​​I was such a kid, I was 22 when we met. It’s taken me until 40 to get my head out of my ass. You can’t make that decision when you’re 22 years old. I wasn’t ready, and he was too good for me.”

​​Who was Brad Pitt with before Jennifer Aniston?

Brad Pitt had several high-profile relationships before he met his first wife Jennifer Aniston. One of the people he dated directly prior to his relationship with Aniston was Gwyneth Paltrow, who he was with —and even engaged to—from 1994 to 1997. He also dated Meet Joe Black co-star Claire Forlani circa 1998 before he began dating Aniston later that same year.

How did Brad Pitt meet Juliette Lewis?

Juliette Lewis and Brad Pitt met on the set of the 1990 tv movie Too Young to Die? when he was 26 and she was … 16. Yikes, ugh, and gross! The pair reportedly dated from 1990 to 1993. Pitt reflected on the relationship in 1994 to Rolling Stone saying, “We were trying to be Sid and Nancy or something. We were idiots. We were just having a great time."

How old was Juliette Lewis when she started dating Brad Pitt?

This answer may diminish your attraction to Brad Pitt by quite a bit. Juliette Lewis was only 16 when she met 26-year-old Brad Pitt on the set of their 1990 TV movie Too Young to Die?. However, the pair claim they didn’t start dating until after filming on the project wrapped, when Lewis was 17. The couple quickly moved in together and cohabitated for three years. The relationship lasted from 1990 to 1993.

It would appear their different ways of thinking contributed to the breakup, which Pitt opened up about to Vanity Fair in 1995. “I still love the woman. There's some real genius there. I had a great time with her. Look, I don't want to go into an explanation. She has her own views, and I respected those views. She does know people. It was one of the greatest relationships I've ever been in. The problem is, we grow up with this vision that love conquers all, and that's just not so, is it?" …Or maybe adults just shouldn’t date teenagers, eh Brad?

Related: 5 Things You Didn't Know About Brad Pitt

Who was Brad Pitt dating when he made Legends of the Fall?

It is rumored that Brad Pitt and his Legends of the Fall co-star Julia Ormond shared a romance behind the scenes during the filming of the movie. However, neither have confirmed the relationship publicly.

If the pair were involved romantically, it would appear it was short lived as Pitt brought Czech model ​​Jitka Pohlodek to the movie’s premiere.

How many times has Brad Pitt been engaged?

Brad Pitt has reportedly been engaged four times—that we know of! Pitt was first engaged to his Cutting Class costar Jill Schoelen for three months in 1989 before she broke it off to date the director of a movie she was working on.

Next, Pitt was engaged to Gwyneth Paltrow, who he was in a relationship with from 1994 to 1997; the two called things off prior to walking down the aisle.

Pitt began dating Jennifer Aniston in 1998 and proposed a year later before tying the knot in 2000. The marriage lasted for five years before the two divorced in 2005 amid rumors Pitt was having an affair with Angelina Jolie on the set of 2005’s Mr. and Mrs. Smith.

Speaking of Jolie, Pitt and Jolie dated for almost a decade before getting married in 2014, after getting engaged in 2012. Sadly, the two separated in 2016 and have been declared legally single as of 2019.

Related: Brad Pitt Rocks a Linen Skirt for Red Carpet Premiere

Who has Brad Pitt dated in the past?

Ah, the question on everyone’s minds. We have already discussed some of the relationships Pitt has had: Jill Schoelen, Juliette Lewis, Jitka Pohlodek, Gwyneth Paltrow, Claire Forlani, Jennifer Aniston, and Angelina Jolie. We’ve also discussed his rumored relationships with Julia Ormond and Geena Davis. But, it should come as no surprise that these are just scratching the surface of Brad Pitt’s romantic history.

Pitt reportedly dated British singer Sinitta between 1984 and 1986, on and off.

He is said to have dated actress Shalane McCall while he had a stint on her show Dallas as her boyfriend between 1987 and 1988—when she was still a teenager. In a 2023 interview with W magazine, Pitt said his favorite sex scene of all time was with a then-15-year-old McCall while filming Dallas. He would have been between 23 and 24 years old at time.

"It would have been in the show Dallas," he said of his favorite love scene. "I had to roll around in the hay in a barn. I don't think I had a line. I was just rolling and frolicking."

He had a brief romance with Christina Applegate in 1989 before she broke up with him for another man.

The same year, Pitt dated E.G. Daily, aka Dottie from Pee-Wee’s Big Adventure and the voice of Tommy Pickles, for a short time.

Also in 1989 (big year for Brad!), Pitt had a short but dramatic fling with Robin Givens, which was rumored to have caused some issues with her estranged husband Mike Tyson.

During the making of 1994’s Interview with the Vampire, Pitt entered into a romance with co-star Thandiwe Newton that apparently lasted for about a year, though the pair kept things low-key.

Following his breakup with Angelina Jolie, Pitt dated married German model Nicole Poturalski around 2019 but the relationship was brief, ending in October 2020. The actor has also been linked to actress Alia Shawkat, but the pair claim to just be friends.

Next, check out Jennifer Aniston's romance history—including details on her marriage to Brad Pitt.