The Truth About Brad Pitt's Post-Divorce Dating Life

Who would have thought one of the world's sexiest men would be struggling to score a date?

By Sarah Grossbart Sep 30, 2019 10:00 AMTags
Brad Pitt, Ad Astra premiereJordan Strauss/Invision/AP/Shutterstock

Who could have possibly imagined a time when women would be scrambling to deny reports that they were dating Brad Pitt

Messy, excessively drawn-out divorce aside, this is Brad. Pitt. Six-time Oscar nominee, two-time recipient of People's Sexiest Man Alive honors, the man who stumped for everyone to have the chance to wed and raved about having children, "It's a true joy and a very profound love. You can write a book, you can make a movie, you can paint a painting, but having kids is the most extraordinary thing I've ever taken on."

And yet most recently it was spiritual healer and jewelry designer Sat Hari Khalsa who has joined a not all that short list of ladies who have emphatically denied they were ever romantically involved with the 55-year-old actor, a source decrying a report that the friends had upgraded their platonic relationship as "entirely false." 

Sure, the pals attended the Sept. 18 after party for his latest film, Ad Astra, but Khalsa interacted far more with a female friend than Pitt, a fellow reveler told E! News: "At no point during the party did there appear to be an obvious PDA or any indication that they were romantic." 

Brad Pitt's Dating History

It's not like Thelma and Louise's hunk suddenly became unloveable. Sure, his in-limbo marital status with Angelina Jolie (a bifurcated judgment handed down in April rendered the actors officially single, but there's still more to be hashed out before the divorce is declared official) complicates any dating situation and the idea of becoming an instant mother figure to a brood of six may intimidate some potential paramours. (See: Tiffany Haddish who joked, "I don't know if I could deal with a man that's got that many kids.") But age has been kind to the Missouri native. His 5-foot-11 frame remains as chiseled as ever and his emotional awareness is at an all time high. While examining his role in the dramatic 2016 split from Jolie, 44, he embraced therapy and the art of taking responsibility for his downfalls. 

So, yeah, it's not so much that the Once Upon a Time in Hollywood star is continually striking out with the opposite sex (who could resist his reportedly humble pick up line?) as he was never actually trying to date these women in the first place.

People don't like to see their beloved screen idols floundering about alone so the question of, "Hmm...I wonder why did they split?" tends to be quickly followed by, "Who will they date next?" And with Pitt not yet providing an answer, fans are eager to fill in the blanks, pairing him off with any woman he chats with longer than it takes to say hi and make some off-handed comment about the weather. 

The first woman to get the next Mrs. Brad Pitt treatment was Kate Hudson. The coupling was pretty much sealed when the then-single actress went on Howard Stern's radio show mere days after Pitt's split and shared that while a personality is great and all, she was really looking for a man that inspired more lust than laughs. 

"You know what I really want right now? Honestly—I'm just gonna be honest—I want funny. Funny makes me happy. But I just want someone really hot!" she shared. "Like, I just want, like, a hot guy right now. Not quite for life, you know."

When the host suggested someone with Pitt's pedigree, Hudson played along, replying, "Yes! I think Brad is very, very handsome." But when he pointed out that he was available should she be interested, she demurred, "Oh god, Howard!" 

No matter, they were soon paired off, enjoying supposed nights of passion and even moving in together before a "bitter" Hudson dumped him when he refused to marry her just months into their courtship. Or, at least, that's the thoroughly dramatic storyline that played out across magazine covers. 

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To be fair, they definitely looked the part. And they had the whole parenting and longtime Hollywood veterans thing in common. And there was the added factor of her brother Oliver Hudson, who couldn't resist keeping the rumors alive. When Star printed that Pitt had moved into the actress' L.A.-area home in early 2017, he jokingly posted to Instagram, "Yeah and it's been hell!! He's messy as s--t! He drinks out of the f--king carton and leaves the door open when he's taking a dump!! And this is when he's at MY house!!!"

What's more, he continued, his mom Goldie Hawn hadn't been able to resist flirting with the star, "She's wearing these little nighties around the house now?! But ALL DAY!! Like at 3pm! And Pa just keeps saying "All right!! It's Brad Pitt!!" Anyway not going well."

Not content to give her brother the final word, the 40-year-old finally addressed the fauxmance on an episode of Bravo's Watch What Happens Live that November and the truth was, she wasn't mad about it. 

Brad Pitt & Angelina Jolie's Famous Exes

Sure it was "the craziest rumor of all time," she told host Andy Cohen noting that they hadn't actually crossed paths "in, like, four years." But she wasn't exactly complaining about being linked to the Moneyball star. "It was kind of an awesome rumor," she joked. "I kind of liked it. I was like, 'OK, fine. We're having twins!'" 

Plus the chatter gave her cover as she developed a new relationship with musician Danny Fujikawa, a longtime friends she met through pals Erin Foster and Sara Foster. (Fujikawa is their stepbrother.) "I've known him for many years, but we never saw each other like that until a year ago now—well, last December, where we just sort of looked at each other and went, 'Oh, wow. This is weird. I really like you,'" she shared with Cohen. "And the rest is history."

Indeed, the duo welcomed their first child together just shy of a year ago, daughter Rani Rose Hudson-Fujikawa, so safe to say Hudson is firmly off Pitt's list of options. 

J. Countess/WireImage

As is Sienna Miller who was none too pleased to be linked to Pitt, a producer on her drama The Lost City of Z. Spotted chatting during a 25-person dinner for the flick in April 2017, the duo were instantly paired off in the press, a rumor, the 37-year-old Brit told Page Six, she wasn't "going to even dignify" with a response. "It's predictable and silly." 

It became more plausible when they met up at England's famed Glastonbury Festival in June (Pitt was attending with Miller's American Sniper costar Bradley Cooper), but a source insisted to Us Weekly that the group "were all hanging out as friends," and not, as The Sun suggested, so crazily in lust that they were unable to keep their hands off each other. Said the source, "There's nothing going on there." 

Ditto with Elle Macpherson, who took a turn being painted as Pitt's leading lady when Australia's New Idea reported they had been on an intimate date in a Hollywood nightclub complete with hair flipping and arm touching.

And same for Charlize Theron and Jennifer Lawrence. Though the latter, set to wed Cooke Maroney any time now, admitted on Watch What Happens Live that she wasn't all that bothered by her temporary status as Pitt's paramour. I've met him once in like 2013, so it was very random," she said in a March 2018 appearance. "But, I also wasn't like, in a huge hurry to debunk it."

Getty Images / FilmMagic

Then Pitt had what we'll call his George Clooney phase. 

Pairing him off with MIT professor Neri Oxman, a renowned expert in architecture, made sense. His old pal Clooney had found love with a non-Hollywood type who seamlessly stepped into his world, often outshining him, so why wouldn't it work for Pitt? And he was certainly intrigued by Oxman. The daughter of two professors The New York Times dubbed "architectural royalty," she spent time as a first lieutenant in the Israeli air force and in medical school before earning her Ph.D. in design computation at M.I.T. 

Having long been passionate about the field, renovating his own homes and building sustainable housing in New Orleans' Lower 9th Ward, Pitt visited one of her classes last November and found the Associate Professor of Media Arts and Sciences to be "brilliant," a source told E! News. "He's interested in getting to know her more and learning from her."

The one snag, of course, as we all learned in an October 2018 New York Times profile of the Cooper Hewitt Design award winner, was that she was otherwise entangled with Harvard-educated billionaire hedge funder William A. Ackman. And theres was no casual affair. By January they had wed quietly in a New York City synagogue. They welcomed their first child months later. 


That's not to say Pitt is feeling down and out. In between doing the Hollywood movie star thing—the September release of Ad Astra came just on the heels the highly anticipated Once Upon a Time in Hollywood—and focusing on the relationship with his kids, he's found time to date, a source reveals. But after spending the last 20-plus years in serious relationships, first with former fiancée Gwyneth Paltrow, then ex-wife Jennifer Aniston, then Jolie, he's been understandably fastidious about the process and, says the source, "doesn't have anyone serious in his life." 

 Those that have been shipping the return of Brad and Jen since she announced her separation from husband Justin Theroux received the gift of hope in February, when Pitt turned up to celebrate her 50th birthday. Alas, his presence at the Sunset Tower affair wasn't a sign of things to come, but rather a natural continuation of their friendly exes status, the two taking to exchanging the sporadic text over the years. 

"Someone extended the invitation to Brad to come to Jen's party and he accepted," a source explained to E! News. "He wanted to support Jen and it was a momentous occasion. But that's the extent of it. It was a social evening with a lot of people who have been a part of her life. They definitely aren't dating or on that path. They are friendly, but that's it." (For the record, his revisiting his Jolie romance is equally as unlikely.) 

Pitt is far more interested in looking forward than reminiscing on the past. Though his heartthrob shelf life is nowhere close to expiring, Pitt is heavily leaning in to his second act. 

Having recently dubbed acting a "younger man's game" he's focused on picking winners for Plan B, the production company behind Moonlight, 12 Years a Slave and If Beale Street Could Talk. "It'll be fewer and father in between for me, just because I have other things I want to do now," he noted in a recent interview with The New York Times. That list includes pursuits both solitary (sculpting, landscaping) and social (the profile notes he wasn't on hand to watch Moonlight lose, and then win, the Oscar for Best Picture because he attended a spaghetti dinner at director pal James Gray's house) but nothing too conventional like curating his own Instagram account. ("Never gonna happen," he told E! News.) 

"When you feel like you've finally got your arms around something," he said of his pivot toward work behind the camera, "then it's time to go get your arms around something else."