Dating Disaster

Six years after ending her second marriage, the Morning Show star Jennifer Aniston is still single - but not for a lack of trying

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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-horrorfilm-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."