All the Ladies Who Have Reportedly Been Romanced by Brad Pitt

During Brad’s four-episode stint on Dallas in 1987, the 24-year-old actor reportedly had an eyebrow-raising relationship with his 15-year-old costar, Shalane McCall. Shalane ended up being Brad’s first onscreen kiss (which you can check out here, if you’re into that sorta thing), but not much ever came from the relationship after he left the show.

Between 1987 and 1988, Brad dated British singer Sinitta, after begging his agent to call hers after he saw her on TV and fell in love. Sinitta later dumped the actor before he shot to fame in Thelma & Louise but looks back on their time fondly. “He was beautiful with the most amazing body,” she said. “I saw him for two years. He was fun, he was young and very sweet.”

In 1989, one of Brad’s very first roles was as a guest star on Robin’s sitcom, Head of the Class. They apparently struck up a connection but ended the affair after Mike Tyson – Robin’s estranged husband at the time – caught them in bed together and threatened Brad’s life.

Brad and Christina briefly dated in 1989, until the Married With Children actress took him as her date to the MTV Movie Awards that year, only to famously ditch him halfway through for another guy.

After meeting on the set of the horror movie Cutting Class, Brad dated actress Jill Schoelen. He popped the question and they were engaged for three months in 1989, until she started dating the director of another movie she was working on and dumped Brad.

The pop singer (and the voice of Tommy Pickles on Rugrats, NBD) was rumored to have dated the struggling actor after his breakup with Jill in 1989.

Brad, then 27, still had yet to make it big in Hollywood when he entered into a high-profile relationship with his 17-year-old Too Young to Die? costar Juliette. They dated from the end of 1989 to 1993, and Juliette still has nothing but kind things to say about him years later. “It amazes me that people are still fascinated that we went out for four years,” she said in an interview with the Daily Mail in 2010. “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 with a fun, smart guy. Then it was over and he went on to become incredibly famous.”

Brad’s steamy sex scene with Geena in 1991’s Thelma & Louise officially earned him the label of Hollywood’s newest sex symbol, and his costar took notice. The pair unofficially dated for a year after production on the movie wrapped, although Jason Priestley (Brad’s former roommate) told The Hollywood Reporter that the much-more-famous Geena made sure all of their meetups were done in secret.

Brad and Julia played lovers in the 1994 drama Legends of the Fall, and despite the fact neither ever acknowledged their relationship publicly, rumors about a real-life romance swirled.

Brad dated then-22-year-old Thandie for a year after they met on the set of Interview with the Vampire in 1994. They had an amicable split and supposedly remained friends.

Brad walked hand in hand with Claire on the red carpet for their movie, Meet Joe Black, in 1998, which had everyone buzzing about a potential romance.

Demi reportedly had a very brief fling with Brad in 1998.

Brad dated Gwyneth between 1994 and 1997, after they met on the set of the 1995 thriller Se7en. Their relationship was extremely public, with Brad proposing in 1996 and referring to Gwyneth as “my angel” and “the love of my life” in his speech at the Golden Globes that same year. They called off their engagement seven months after he proposed, and in January 2015, Gwyneth filled Howard Stern in on her relationship with Brad:

“I definitely fell in love with him. He was so gorgeous and sweet. I mean, he was Brad Pitt! My father was devastated [when we split]. 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.”

Related: Gwyneth Paltrow's Most Precious Pictures With Her Kids

Brad and Jen reportedly met in 1998 after their respective agents set them up on a blind date. The Hollywood golden couple continued to date for two more years before Brad popped the question, and they had a lavish, $1 million wedding in Malibu. In 2004, Brad started shooting Mr. and Mrs. Smith with Angelina Jolie after Nicole Kidman pulled out of the film. This, combined with reports of Jennifer not wanting to have kids, led to nonstop rumors about the couple. Jennifer filed for divorce in 2004 after four and a half years of marriage, and Brad went on to marry Angelina.

Related: 12 Jaw-Dropping Facts About Brad Pitt and Jennifer Aniston's Million-Dollar Wedding

Given their somewhat rocky start, everyone assumed that Angelina had to be, without a doubt, the love of Brad’s life. The pair were inseparable after Brad’s split from Jen in 2005 and now share six children together: Maddox, Zahara, Pax, Shiloh, and twins Knox and Vivienne. Their history made their divorce all the more shocking, with rumors of the reasoning behind the split ranging from Angelina not agreeing with his parenting style, to him having a reported affair with Allied costar Marion Cotillard.

Related: Bet You Forgot About Angelina Jolie's Other Famous Flings

Brad and Sienna first sparked dating rumors in April 2017 when they were spotted chatting most of the night at a Lost City of Z dinner event in LA. According to Us Weekly, the actor has had a few meetups with Sienna, who starred in his 2016 film, The Lost City of Z, and “they’ve been spending some time together.” While both parties never confirmed the relationship, it’s also worth noting that they linked up again two months later at England’s Glastonbury Festival with pal Bradley Cooper.