Dinner Parties, Dating and Befriending the Fab Five: How Life Has Changed for Justin Theroux Since His Split With Jennifer Aniston

Six months removed from his existence as Mr. Jennifer Aniston, the actor "is having the time of his life," one source reveals.

By Sarah Grossbart Aug 10, 2018 10:00 AMTags
Watch: Justin Theroux Recalls Heartbreaking Breakup Story

Appearing as the title character in a film called The Spy Who Dumped Me means you're going to be asked about past breakups. And ever the good sport, Justin Theroux was game to deliver. 

No, not that one of course. But the Washington, D.C.-born actor was willing to dish to E! News about one of the more traumatic splits of his youth—a separation that saw him playing the role of dumpee. In the months before he was set to head off to Vermont's Bennington College, he and his high school girlfriend were battling through a long-distance relationship. "I was working and she was crying on the phone to me all the time going like, 'It's our last summer together,'" he explained of his decision to make an unannounced, and ultimately unfortunate, drop in. "And I came back and she was schtupping a guy who was, like, in her bed. It was a terrifying experience! I went to surprise her." 

He was the one left stunned. And while the walk-in encounter was definitely on the low end of the sliding separation scale, none of them are good. "It sucks whether you're breaking up with someone who really likes you or if they're breaking up with someone and you really love them, it's the worst," he stressed. "There's no good side of that coin to be on."

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Not that he's feeling particularly short-changed these days. In fact, the birthday boy (he turns 47 today) seems downright content with his lot in life. To hear friends tell it, his marriage to Jennifer Aniston was finished long before they announced their Valentine's Day split, which means The Leftovers regular had plenty of time to grieve the seven-year romance before he to go out in public appearing like he was okay with the whole thing. And by all accounts, they both really, really were fine. Save for communiqué dispatched between their attorneys as they amicably sort out financials, Theroux and his former bride, 49, "have had minimal contact," one source revealed to E! News in the weeks after the split. "They have completely moved on and are not looking back." 

For Theroux, that meant physically moving some 3,000 miles away from the memory-laced Bel-Air home he once shared with Aniston and a West Coast existence that never fully suited him. "Justin is living life exactly how he wants to be in New York and has moved on from his L.A. life with Jen," reports an insider, noting he's relieved to no longer be shielded by bodyguards and security gates. "He's very happy with where he is." 

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That would be downtown Manhattan, to be exact. Back in the place he called home for decades before crossing paths with Aniston on the set of their 2012 comedy Wanderlust, he's settled into a familiar routine of roaming the sidewalks relatively unnoticed and popping into stores and coffee shops on a whim. This is a man who decided to try skydiving because "I happened to be driving by a skydiving school," he told Men's Health. He's not meant to be penned in. 

While his actor status means there's often at least one photographer on his trail, Theroux feels free to grocery shop like your average New Yorker, meet a friend to test out a new restaurant or traverse the cobblestone streets aboard his bike, ever present backpack along for the ride. 

Sometimes he'll be off to a meeting, discussing a new project that's piqued his interest. "I learned—not early, but at some point—if you do the things you like to do, you'll produce better work," he explained to Men's Health. "When you're doing things you don't want to do, the work suffers. How could it not? You're not interested in it. I gravitate toward the next thing I think I'll enjoy, as opposed to things I think would be smart to do, or a good career decision." 

Jennifer Aniston & Justin Theroux: Romance Rewind

Right now his great loves include sparring in the boxing ring with trainer Rob Piela at Gotham Gym and entertaining friends, the latter requiring him to ensure his West Village pad is stocked with his go-to Casamigos tequila at all times. "He's been hosting and attending a lot of different friendly gatherings and is trying to keep himself around friends a lot more than he used to," an insider tells E! News.

Rather than risk being home alone and moping about the divorce, says the insider, he'll do things like oversee a dinner party for Le Turtle restauranteur Carlos Quirarte. (The March fete saw him circulating cocktails and chatting up longtime pal Amy Sedaris.) Says the insider, "He's just trying to stay busy and stay happy." 

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That means, perhaps, picking up a few new friends as well. Having binge watched the first season of this winter's runaway hit Queer Eye on Netflix, "I did one of those things I've never done before in my life," he recalled to good pal Jimmy Kimmel last month. Mid-preparation for an Easter quiche he went on social media and noticed grooming expert Jonathan Van Ness was in New York and, therefore, potentially free for a low-key hang. "I was just like, 'I'm just going to DM him,'" he said. "I was like, 'Hey you probably won't get this, but this is Justin and I'm making a quiche." 

As most anyone would when receiving a message from Jen Aniston's rugged former spouse, Van Ness answered "immediately," recounted Theroux. The stylist, along with costars Tan France and Antoni Porowski, are now regulars at Theroux's place though they've yet to voice their opinions on his midcentury taste and penchant for skinny jeans and sleeveless shirts. Perhaps because faced with a picture of Theroux and his new buddies, one would be hard pressed to quickly identify the actor amongst the reality show tastemakers, so we're going to guess his wardrobe gets their hard-earned approval. 

He's easily acclimated himself, teaching the group to draw vaginas (as you do when, as he said, you're "dying to know what in their brain that looked like,") cutting up a tee for Van Ness to wear as a fringed crop at NYC's June Pride Week and going on grocery runs to ensure he has top-notch ingredients at the ready should chef Porowski want to whip up some nachos. "I'm usually the one doing the shopping," he told Kimmel, "like, 'Oh my God the guys are coming over." 

Sometimes their foursome expands to include others, like, say, Emma Stone. But Van Ness insists the Maniac costars are, as Theroux once wrote on Instagram, "JUST bfffffs." Asked about their closeness at the May 31 NETFLIXFYSEE event, Van Ness told E! News, "They're friends. We're all friends. Men and women can be friends and it can just be friendly." 

Friends with deep bank accounts, a healthy stash of frequent flier miles and work obligations that take them to fantastic spots like the south of France. That's where Theroux and the 29-year-old first got the ol' rumor working in late May. 

Coming off a joint appearance at Rihanna's Met Gala after-party at NYC's see-and-be-seen spot Up & Down (a source says they sipped Armand de Brignac bubbly and "were together all night,") and a late-night dinner at Blue Ribbon Sushi in the city's Soho neighborhood, an afternoon spent lounging at one of Hotel du Cap-Eden-Roc's cliffside cabanas was enough for people to question, wait, are they a thing? 

Alas, the Louis Vuitton brand ambassadors were fresh from a work trip to the brand's French fashion show and spent much of their time in a group hang setting with Sienna Miller, Spiderman: Homecoming actress Laura Harrier and journalist Derek Blasberg.

So put Stone in the just buds category, along with Jennifer Lawrence, who hosted the pair of them and Blasberg for a rooftop dinner at her New York apartment in June that saw the group taking a series of selfies to capture the breathtaking view. 

Still, Theroux wouldn't mind finding someone to spend nights with other than his newly adopted pit bull Kuma. "He's casually dating, but it's nothing more," reveals one source. "He's enjoying being social and meeting people from all walks of life." 

Jennifer Aniston and Justin Theroux: Sweetest Quotes

And until one of those encounters stops him in his tracks, he's content to travel the world, hang out with his bros and test out whatever activity happens to cross his path. (Get another tattoo? Sure. It's something he does "kind of when the mood strikes.") As he told Men's Health of his patented devil-may-care persona, "There are things I know I will do. I just don't know what they are yet." 


For now, the only thing gnawing at him is to get out and enjoy life. "He doesn't have anyone else to be responsible for or to report back to and he's taking advantage of that," explains the source. "Justin is hanging out and having the time of his life." 

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