Everything to Know About Brad Pitt's Romantic History Before Girlfriend Ines de Ramon

Brad Pitt may be known for taking his shirt off in movies, but he tends to keep whatever's happening in his life close to the vest.

Or he tries, anyway, but the man has to go out sometimes!

While some of his romantic highs and lows have been unavoidable as far as public consumption is concerned, Pitt having married-and-divorced two of the most famous women alive, he tends to strive for a quiet private life when possible.

And that's what he appears to be sharing these days with Ines de Ramon, who was first spotted in the actor's company in November 2022 and this past August was seen sporting a "B" charm necklace. (And we know, thanks to Meghan Markle, that initial jewelry is laden with meaning.)

The date night sightings have continued, the pair enjoying LACMA's Art+Film Gala together last month, so it appears that Pitt is turning 60 on Dec. 18 as one-half of a couple.

Which, incidentally, means this relationship is the first notable update to his storied dating timeline since he and Angelina Jolie split up in 2016.

Because, having been in Hollywood for 40 years, Pitt has naturally met his fair share of women, many of whom he ended up dating. (Remember, one man's fallow period is another's much-needed pause to regroup and recharge.)

So in honor of Pitt's 60th birthday, we're gifting you his stacked romantic history. It's not as long as his filmography, but it's epic all the same:

The "Toy Boy" singer dated Pitt off and on for several years in the '80s, long before every couple had a clever one-word nickname—so when the pop star was asked in 2016 what their cutesy name could've been, she suggested "Braditta."

Brad played the actress' boyfriend Randy on four episodes of Dallas between 1987 and 1988 and was rumored to have romanced her off-camera as well. But in 1989, when she was 17, McCall married current hubby Trent Valladares and never looked back.

Pitt's first fiancée! The Cutting Class co-stars had been engaged for three months when, claiming loneliness, Schoelen pleaded with Pitt to visit her in Budapest, where she was shooting a movie. "At this point I had $800 to my name and I spent $600 of it getting a ticket from Los Angeles to Hungary to see her," Pitt reportedly told The Sun in 2011. "I got there, went straight to the set where she was filming and that night we went out to dinner. She told me that she had fallen in love with the director of the film. I was so shocked I said, 'I'm outta here.'" Love works in mysterious ways.

Pitt scored an appearance on the Riverdale actress' sitcom Head of the Class in January 1989. The ink on Givens' divorce from Mike Tyson wouldn't be dry until that February, however, and the boxing champ later recalled seeing Pitt toking away when he came across him at his estranged wife's house one morning—where Tyson says his intent was to have a quickie while on his way to see his divorce lawyer.

"She drives up with the handsome Brad Pitt," he said while telling the story, then a sample anecdote from his one-man show, on Conan in 2012. "I said, 'aw man, I ain't gonna get no p--sy, f--k.'" Andy Richter chimed in, "Brad Pitt is the international symbol for that."

The tale continued to be a favorite for interviewers over the years, with Tyson concluding on The Real in 2016, "I didn't really catch them in the act—maybe before the act...He's a really nice guy."

Pitt was the Married...With Children star's date to the 1989 MTV Video Music Awards—and though she has remained mum on the subject, Skid Row rocker Sebastian Bach insists that he was the guy Applegate infamously ditched her up-and-coming-actor date for that night.

Pitt also dated Dottie from Pee-Wee's Big Adventure in 1989. He may have had that rebel look, but Daily would later describe him as a "laid back, very earthy" guy, and not "super Hollywood." "He's the kind of guy that would pick up and leave and drive his car just to get out of the city," she told DailyMail.com in 2016.

Pitt rocked Davis' world onscreen as a hustling hitchhiker in 1991's Thelma & Louise, which proved to be the actor's (and his abs') true breakout role—and Pitt's onetime roommate Jason Priestley claimed in his 2014 memoir that they were an off-screen item as well. 

"I actually read with him first—there were five candidates for the role," Davis recalled Pitt's audition to The Hollywood Reporter in 2014. "And then he came in—this is so embarrassing—but I got a little distracted during the scene, you know? I was forgetting my lines. I was like, 'I'm totally screwing up this kid's audition.'"

These two played murderously dysfunctional couples twice, in the 1990 TV movie Too Young to Die? and the gritty 1993 thriller Kalifornia, but real life seems to have been sweeter during the several years—he was her Oscars date in 1992 when she was nominated for Cape Fear—they were together.

"I still love the woman," Pitt told Vanity Fair in February 1995. "There's some real genius there. I had a great time with her...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?" In 2010 Lewis told Pop Tarts that she and Pitt "run into each other on and off and we say hello and that is really nice."

Brad has described his experience making Interview With the Vampire as "miserable." He told Entertainment Weekly in 2011 that "the great thing that came out of that movie is that it birthed my love affair with New Orleans." 

But the shoot also birthed a brief relationship with Newton, who had a small role as Yvette, a servant on Pitt's character Louis' plantation.

The Czech model was Brad's date to the 1994 premiere of Legends of the Fall, which sent the actor's heartthrob status skyrocketing—and they were dating when Pitt told Vanity Fair he still loved Juliette Lewis.

Pitt's the one who lost his head for Paltrow on the set of 1995's Se7en. They were the mid-90s couple, from the top of her slip dress to the ends of his frosted tips. Accepting the Best Supporting Actor Golden Globe for 12 Monkeys in 1996, Brad thanked Gwyneth, his "angel, the love of my life," and he proposed that December. They even had matching haircuts at one point.

"I take the institution extremely seriously. There are no divorces in my family either—and in his either, so this is not something—we've been together for quite some time, so this is not a rash decision," Gwyneth convincingly told Entertainment Tonight about their engagement. But in June 1997, they broke up.

"When two people aren't supposed to be together, they're not supposed to be together," a defiant Paltrow said in 1998. Fast-forward to 2015, when she told Howard Stern, "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."

Moreover, her dad, Bruce Paltrow, was "devastated" when they broke up. "My father loved him like a son." Ultimately, Paltrow said, "I definitely fell in love with him. He was so gorgeous and sweet. I mean, he was Brad Pitt!"

After his breakup with Gwyneth, Brad's said to have briefly dated his Meet Joe Black co-star. They attended the 50th Annual WGA Awards together.

The story goes that Jen met Brad in 1998 on a blind date set up by their agents. The world still not one for smushed-together names yet, they were simply "Hollywood's golden couple." They married in 2000, Pitt guest-starred on Friends in 2001 and in 2002 Aniston said of starting a family, "Absolutely it will happen but probably not for a while."

Alas, on Jan. 8, 2005, the actors announced they had "formally" separated. "For those who follow these sorts of things, we would like to explain that our separation is not the result of any speculation reported by the tabloid media," they said in a statement. The divorce was finalized that October amid all sorts of reports perpetuated by the people who do follow these sorts of things.

Meanwhile, Aniston's September 2005 Vanity Fair interview will go down in history as one of the rawest, most poignant breakup postmortems in celebrity history.

But years later...they're friends!

The Oscar winner eventually admitted that she and a still-married Pitt had fallen in love during the making of Mr. and Mrs. Smith in 2004.

Spurred on by their kids—Maddox, Zahara, Shiloh, Pax and twins Vivienne and Knox— Brangelina finally married at their chateau in France in 2014 after being engaged for two years.

"You get together and you're two individuals and you feel inspired by each other, you challenge each other, you complement each other, drive each other beautifully crazy," Jolie told Elle in 2014, before the surprise nuptials. "After all these years, we have history—and when you have history with somebody, you're friends in such a very real, deep way that there's such a comfort, and an ease, and a deep love that comes from having been through quite a lot together."

But Jolie filed for divorce on Sept. 19, 2016, citing irreconcilable differences and triggering an FBI investigation into Pitt's behavior on an overseas flight (he never faced charges). And though there have been periods where the dust seemed settled, the aftermath got messy and stayed messy.

After he and Jolie broke up, Pitt was rumored to be seeing a number of women, from Alia Shawkat to jewelry designer Sat Hari Khalsa to architecture professor Neri Oxman.

All filed under "just friends" in the end.

But Pitt is reportedly in a real-deal relationship with de Ramon. He was first spotted with the jewelry company executive in November 2022—two months after de Ramon and husband Paul Wesley confirmed they had been separated since the spring. (The Vampire Diaries alum filed for divorce in February 2023.)

Meanwhile, the sightings of Pitt and de Ramon, though sporadic, simply haven't stopped.