In the spring of 2005, Jennifer Aniston filed to divorce Brad Pitt after nearly five years of marriage.
A few years later, he and Angelina Jolie confirmed widespread speculation they’d had an affair while he was still with Jen, confessing — him to Rolling Stone, her to The New York Times — they “fell in love” while filming Mr. & Mrs. Smith in 2004.
“There are many stages of grief,” Jen told Vanity Fair weeks before her first divorce was finalized. “It’s sad, something coming to an end. It cracks you open … when you try to avoid the pain, it creates greater pain.”
Going through such a public split was a trial rife with “anger,” “hurt” and “embarrassment,” admitted the Friends star, who tried “really hard to rise above it.”
And she did. A decade later, she wed Justin Theroux, 53. But in 2017, they, too, went their separate ways, though their breakup was far less dramatic, with Justin telling The New York Times it was “gentle,” “amicable” and “as painless as it could be.”
Looking back, Jen “readily admits to friends she’s been unlucky in love,” a source exclusively tells Life & Style.
However, she doesn’t see her biggest breakups as failures.
“My marriages, they’ve been very successful,” she insisted to ELLE in 2018. “When they came to an end, it was a choice that was made because we chose to be happy, and sometimes happiness didn’t exist within that arrangement anymore.”
Since then, Life & Style’s source confirms that Jen’s healed, moved on “and hasn’t given up on finding love again” at age 56. That hope endures, explains the source, “because she’s made peace with her past.”
Jennifer Aniston’s Good Vibes
The Morning Show star isn’t holding grudges. In fact, just the opposite.
“Brad and I are buddies,” she told radio host Howard Stern in 2021. “We’re friends and we speak.”
She and Justin have also remained pals. When the Running Point actor married Gilded Age actress Nicole Brydon Bloom, 31, in Mexico in March, “Jennifer was one of the first ones to congratulate Justin,” an insider revealed to the Daily Mail. “She is happy for him.”
Indeed, Life & Style’s source says Jen only wants joy for Justin and Brad, 61, whose divorce from Angelina, 49, was finalized last year after eight years of bitter fighting; he’s currently dating 30-something Ines de Ramon, a jewelry executive.
“Jen has zero ill will and is genuinely thrilled for their successes in love and in Hollywood,” insists the source. “She also thinks, if they can move on, why can’t she?”
Jennifer Aniston’s New Chapter
She wasn’t always sure she should — or could.
“I didn’t want to for a long time, and I loved really being my own woman without being a part of a couple,” Jen told podcaster Bruce Bozzi in 2021. That’s shifted, she added: “I’m ready to share myself with another.”
She also held back in part, says the source, “because she felt maybe she just wasn’t cut out for long-term relationships.”
Now, thanks to a great support system of friends, including Courteney Cox and Sandra Bullock, both 60, and “a lot of therapy,” says the source, “she’s never felt more confident.”
That finally came in her 50s.
“I feel the best in who I am today, better than I ever did in my 20s or 30s even, or my mid-40s,” she shared with Allure a few years ago, explaining that she’s actually learned to be grateful for the “really hard” stuff she went through over the last few decades, including the “challenging road” of trying and failing to get pregnant.
“If it wasn’t for going through that, I would’ve never become who I was meant to be,” Jen said. “I would’ve been stuck being this person that was so fearful, so nervous, so unsure of who they were. And now, I don’t f—ing care.”
Jen is deeply “content,” says the source: “But she would like to fall in love again.”
Though she’s famously dismissed using dating apps, “her friends are always scoping out potential guys for her. They know what she likes — and what she needs.”
And Jen, adds the source, “is open to it all.”
