Once upon a millennium ago, Brad Pitt's agent factored heavily into his romantic life.
He met former fiancée Gwyneth Paltrow on set, ex-girlfriend Juliette Lewis too. In fact he has a not-all-that-short list of actresses (see: Robin Givens, Thandie Newton) that he would go on to date after connecting mid-shoot. And everyone remembers what happened when he signed on to film Mr. & Mrs. Smith with that talented and becoming young single mother.
But before that there was the blind date that launched the golden couple of the early aughts. Set up by their rather intuitive and matchmaking-inclined agents, future spouses Jennifer Aniston and Pitt knew instantly when they broke bread in 1998 that they were destined to become a thing. "We both did on our first date," the Emmy-winning Friends star revealed in a January 2004 interview with Diane Sawyer. "It was weird." Though she was careful not to share she was already considering forever, "I thought it," she said, recalling the excitement that ran through her head. "'Hmm...that's weird. That was a really easy evening. That was really fun.'"
Friends are confident more fun nights await for Pitt, the 54-year-old Oscar winner wading back into the dating pool for the first time in more than two decades. But they certainly won't begin with a call from CAA. "I can't see Brad dating someone super famous again," one source told The New York Post's Page Six this week, "I can definitely see him dating someone with a lower profile."
Not that courting a relative unknown would prevent any romance from becoming headline news.
Because try as he might to remain under-the-radar, having said what he's going to say about his split with Angelina Jolie and the plan for putting the pieces of his life back together in his one tell-all with GQ, Pitt's behind-closed-doors existence is still the source of constant speculation. Never mind that his social life could best be summed up as quiet dinners with pals and the occasional set-up, no one woman yet sticking out as an obvious candidate to become the next Mrs. Brad Pitt.
That hasn't stopped outlets from pairing him off with Kate Hudson, Sienna Miller and Elle Macpherson (all of which firmly refuted the rumors) and, finally, M.I.T. professor Neri Oxman, whose real relationship with billionaire hedge funder William A. Ackman proved to be so serious they recently celebrated their engagement.
"The public obsession with everything he does is just hard," another pal tells the Post. Which is why narrowing his pool of potential mates down to those outside the industry is a sound strategy, two bold-faced names always proving infinitely more interesting to the public than one. Those in his inner circle trusted enough to make introductions (that list includes sculptor Thomas Houseago and Dede Gardner, president of his Plan B production company) are tasked with considering one criteria above all else. "He wants to be with someone nice," the pal says of the father of six, "it's just going to take a while before a long-term relationship can happen."
Because even if someone starts out as a relative unknown in the pop culture realm, once they're linked to someone as high-wattage as Pitt they're unlikely to stay that way. (See: Clooney, Amal.) Agreeing to a date with the Once Upon a Time in Hollywood actor is akin to stepping behind a giant X-ray an undeniable fact that has made dating extra challenging for the star. "There's all this gossip," the source tells Page Six, "and suddenly this person becomes a public character."
Such was the case for Oxman even though she never actually dated the Ad Astra star. Her grave error was agreeing to host the architecture enthusiast at one of her classes last November and being both attractive and brilliant at the same time. Having spent time as a first lieutenant in the Israeli air force and then in medical school before earning her Ph.D. in design computation at M.I.T. and being named the Associate Professor of Media Arts and Scientists, the scholar had a background that left Pitt intrigued. "He's interested in getting to know her more and learning from her," an insider told E! News, "but they are strictly friends."
After months of speculation it was a point Oxman felt the need to emphasize in a New York Times profile. As another source told E! News at the time, "Some people seem to be exaggerating this into something that doesn't exist."
The latest woman to take a spin through the Pitt news cycle is spiritual healer Sat Hari Khalsa. Both close with Red Hot Chili Peppers' Flea, they appeared deep in conversation throughout the Silverlake Conservatory of Music gala the bassist hosted in late September. "They seemed to know a lot of the same people and enjoyed themselves," noted one onlooker. "They had a lot to talk about."
Of course, that could be true of anyone who finds themselves seated across from the jewelry designer who once toured as the band's designated spiritual healer. While one pal described the divorced mother of one to the Post as a "totally awesome" woman with "wonderful energy," it's Chili Peppers frontman Anthony Kiedis who has the highest praise, labeling Khalsa as one of his "main soul mates."
In his 2004 memoir Scar Tissue, Kiedis describes Khalsa as "a sweet, incredibly sheltered, turban-wearing young lady. She looks like a female version of Flea, with the same gap-toothed smile, the same shape of face, the same color eyes, the same little pug nose. She's maternal and she's warm and she's loving and she's unassuming, a complete breath of fresh air and female energy, and I don't mean sexual energy, at least not for me. For me she's like a sister and mother and caretaker and nurse all in one."
She's certainly taken to helping Pitt. An insider tells E! News Khalsa has been making house calls to the actor's L.A. compound. "She's providing him with some guidance and has been a welcome breath of fresh air and spirituality in his life," says the insider. "he feels like he has a lot to learn to better himself."
Right now the pair are in the "getting to know each other" stage, the insider reports and it remains to be seen if she'll be the one to capture is attention for the long-term. Still pushing through his never-ending divorce battle with Jolie as they try to come to an agreement over how to share custody of Maddox, 17, Pax, 14, Zahara, 13, Shiloh, 12, and 10-year-old twins Vivienne and Knox, logging time with his kids remains more important than scheduling date nights.
"He's focused on his children, his work and wanting to have some sense of normalcy," the source tells the Post. "He's dating casually but, for the foreseeable future, everything is about the kids."
Still, his friend tells the outlet they have reason to believe the Missouri native could one day find himself on bended knee again. "Brad comes from a very traditional family," the friend says, noting he's close to his parents, trucking company owner Bill and school counselor Jane, "and his brother and sister are both married with families. I could see him marrying again, but it will be a much more low-key relationship."