Jennifer Aniston Is Tired of Being Single After 6 Years: Dating Has ‘Been Pure Hell’

She was putting herself out there. In late 2022, Jennifer Aniston admitted that after a “challenging” period in her life, she was finally “coming back into the light” — and her heart was open. “I’d love a relationship,” she confessed. “There are moments I want to just crawl up in a ball and say, ‘I need support.’ It would be wonderful to come home and fall into somebody’s arms and say, ‘That was a tough day.’”

But on the cusp of her 55th birthday next month, she’s still searching for Mr. Right. Though the Friends star considers herself “a very independent person,” she says, and has “loved really being my own woman without being a part of a couple,” she’s also been disappointed by many of the men she’s encountered since ending her second marriage, to Justin Theroux, 52, in 2017. “Jen’s had six years of being single and says it’s been pure hell,” shares a source, referring to the actress’ many dating disasters. “She says she wouldn’t wish what she’s gone through on her worst enemy.”

Bad Luck

She’s seemingly a magnet for red flags. “Jen tells a great story about one of the worst dates she’s ever been on,” says the source. “It was with a very handsome studio executive who brought an envelope to their dinner date. After a few minutes of small talk, he pulled out a screenplay for a slasher-horror-film-meets-rom-com he was working on. Not only did he write it, but he also wanted to be in it, opposite Jen as the star. She was flabbergasted.”

Sadly, he’s not the only dud she’s crossed paths with. “There have been a lot of lonely nights,” says the source, noting that Jen’s career success — she was just nominated for another solo Screen Actors Guild Award for her work on The Morning Show, after winning the trophy four years ago — hasn’t spilled over to her dating life. “But she’d rather be alone at home with her dogs than on a date with another boring guy or one who fans out over her days on Friends or asks her to split the bill or asks her for an autograph at the end of the night.”

Despite all the cringe-inducing experiences, the actress has tried to keep an open mind and adapt. “After so many bad dinner dates, her new go-to meeting place is a mall,” says the source, noting that a popular retail and movie theater complex in L.A.’s Century City business district is among her regular rendezvous points. “She’ll wear a hat and sunglasses. She likes it because it’s clean, safe, there are a ton of people around, and she can size up the guy in broad daylight. And if he’s a loser, she can go shopping instead.”

She knows there are better men out there. However, she’s decided she doesn’t want to meet them online. “No Tinders and no Rayas, please. I’m an old-school girl,” Jen’s said of the popular dating apps, lamenting that “people don’t come up to people anymore.”

According to the source, rumor has it Jen did briefly test the waters with “a secret online dating profile,” though “that wasn’t successful either and just confirmed she didn’t like it.”

The Total Package

What she’s looking for in a man is pretty basic. “Chemistry,” she’s said, “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’s admitted, “is also pretty important.”

As she’s gotten older, she’s added to her list of turn-ons. “Fitness is important and not just about, like, how you look,” the health nut has explained. “I want to be around here for a long time and not be in a wheelchair when I’m 80.”

That’s 25 years from now. Twenty-five years ago, Jen had just fallen in love with her first ex-husband, Brad Pitt, 60. Is a third husband in her future? “Never say never,” she admitted a year ago, though added that she didn’t have “any interest” in getting married again at the time. “Jen would like to tie the knot,” insists the source, but “she won’t lower her standards.”

She will, however, “go out of her comfort zone — a blue-collar-type guy with a career and a dad bod is not out of the question. Neither is someone who’s up to 10 years younger,” says the source, pointing out that former flame John Mayer, 46, was already eight years her junior, while bestie Courteney Cox, 59, has been in a relationship with musician Johnny McDaid, 47, for the better part of a decade. “Jen’s really hoping her dating luck changes in 2024.”