Jennifer Aniston has twice been a summer bride. She walked down the aisle for the first time in July 2000 when she married Brad Pitt; they divorced less than five years later in the wake of his affair with Angelina Jolie. Then Jen did it again in August 2015 when she and Justin Theroux exchanged vows. But just two years later, that union ended, too. So would she say “I do” again? “Never say never,” Jen said in a recent interview, “but I don’t have any interest.”

For a long time, that sentiment extended to her dating life, too. “Jen has been burned so many times that she’s more careful than ever when it comes to jumping into a new relationship,” says an insider, explaining that the actress “doesn’t feel like she needs a relationship right now. She’s never been happier and is content enough to be by herself.” Indeed, Jen, 54, recently admitted she’s “a very independent person.” But that doesn’t mean she wouldn’t welcome meeting someone special. “It just hasn’t happened yet,” continues the insider, who claims Jen “hasn’t gone on a single date since Justin. They’ve remained friends, but despite all the reports to the contrary, things never got romantic again for them.” The Morning Show star is hopeful she’ll find a new partner when she’s meant to, says a source: “Jen has been healing and learning to love again.”

In 2021, Jen confessed that amid the pandemic and her work commitments, she wasn’t prioritizing romance. “No one of importance has hit my radar yet,” she said explaining that she didn’t want to share herself with another person “for a long time. I loved really being my own woman without being a part of a couple. I’ve been a part of a couple since I was 20, so there was something really nice about taking the time.”

Digging Deep

But a year later, things had shifted. “I’d love a relationship. Who knows? There are moments I want to just curl up in a ball and say, ‘I need support,’” she admitted in 2022, adding, “It would be wonderful to come home and fall into somebody’s arms and say, ‘That was a tough day.’”

Jennifer Aniston and Justin Theroux
Michael Tran/FilmMagic

Her heart has been through the wringer. “Jen really thought she would start a family with Justin, grow old with him, that he was the one. It was extremely difficult to come to terms with that divorce, maybe more so than her divorce from Brad,” says the insider. “Brad cheated — that was a cruel betrayal. Justin changed the way she felt about love.”

Jen’s done a lot of work on herself since then. “I feel like I’m coming through a period that was challenging and coming back into the light,” she said at the end of 2022, admitting that “intimacy has always been a little [tough to reach]” for her. “I have had to do personal work that was long overdue, [look at the] parts of me that hadn’t healed from the time I was a little kid,” she confided. According to the insider, “Jen has had years of therapy. There have been a lot of tears.”

But there have been laughs, too. Looking back at some of the men from her past, “Jen’s joked that she could write a book about her dating horror stories,” says the insider — “guys who expected her to be Rachel from Friends, who asked why her hair isn’t the same. One actually wanted a selfie and an autograph. Some have even pitched scripts to her or, worse, asked her to pick up the tab.”

What She Wants

She knows there are better men out there. She also knows she doesn’t want to meet them online. “No Tinders and no Rayas, please. I’m an old-school girl,” she says of the popular dating apps, lamenting that “people don’t come up to people anymore.” If a man does approach her, what’s she looking for? “Chemistry,” she says, “and also the ease at which the conversation flows the first time. Confidence, but not a cockiness. Humor, please, I beg of you. Be generous and kind to people.” A first kiss, she admits, “is also pretty important,” of course.

Is she picky? Maybe, but Jen is done compromising. “She’s very selective about who she’ll let into her heart again, but she also knows that she doesn’t need a man by her side to be happy. That’s huge growth for her,” says the source. “She may have lonely nights at times, but she’s at peace with being alone. She’s confident love will come again.”

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