Jennifer Aniston's A-List Status Has Reportedly Led to Some Disastrous Red-Flag Dates

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Jennifer Aniston hasn’t been shy about being open to love again after her divorce from Justin Theroux in 2018. The 54-year-old star may be ready for a relationship, but sometimes it’s hard to date as one of the most famous faces in Hollywood.

Anyone who has been on dating apps knows that it isn’t easy to find the perfect partner, but being an A-list star only adds to those woes. “Jen’s had six years of being single and says it’s been pure hell,” a source told Life & Style. “She says she wouldn’t wish what she’s gone through on her worst enemy.” The insider even detailed “one of the worst dates she’s ever been on.”

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Justin Theroux (L) and Jennifer Aniston attend the 85th annual Academy Awards at the Dolby Theatre. Aniston wears Fred Leighton jewelry with a Salvatore Ferragamo clutch. Theroux wears a Salvatore Ferragamo suit. (Photo by Donato Sardella/WWD/Penske Media via Getty Images)
Justin Theroux (L) and Jennifer Aniston attend the 85th annual Academy Awards at the Dolby Theatre in 2013.

“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,” the source divulged. “Not only did he write it, but he also wanted to be in it, opposite Jen as the star.” Needless to say, Aniston was reportedly “flabbergasted” by the date using her Hollywood power as an opportunity to hold a pitch meeting during their time together. Talk about a red flag!

Aniston apparently tried to meet her match using “a secret online dating profile” which she decided wasn’t the right approach for her. The insider claimed that The Morning Show star is insteadscoping out a very popular “mall” in Los Angeles to possibly meet the man of her dreams. “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,” they noted. “And if he’s a loser, she can go shopping instead.”

The Friends icon believes that her parents’ divorce when she was only nine years old had a big imprint on why she isn’t in a relationship now. “Watching my family’s relationship didn’t make me kind of go, ‘Oh, I can’t wait to do that,'” she told WSJ Magazine of her late parents, Nancy Dow and John Aniston. “It was almost easier to just be kind of solo. So I didn’t have any real training in that give-and-take.”

Before you go, click here to learn more about celebrities who’ve opened up about dating after divorce.

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