Jennifer Aniston’s unfinished business with John Mayer

Bad news, Brad: there's another ex on the scene

Jennifer Aniston John Mayer unfinished business

by Charlotte Oliver |
Updated on

Listen up, Jennifer Aniston: when we said we were happy to see you getting closer to your ex again, we were obviously talking about Brad Pitt – not the guy who’s developed a rep of being a bit of a Hollywood heartbreaker. So, rumours that the star has been meeting up with notorious playboy John Mayer do not bode well. Just saying.

The former couple, who dated from 2008 to 2009 after meeting at an Oscar party, had fans speculating wildly last week, after John posted a video to TikTok of himself cuddling up with his “new doggy playmate”, who just happened to look a lot like Jen’s pup Lord Chesterfield, as well as having the same-looking collar.

Jennifer Aniston John Mayer unfinished business
©Getty

Neither party confirmed nor denied that they were hanging out again, and the rumour mill went into overdrive – especially because Jen is known to harbour a secret soft spot for her ladykiller ex. Well, there’s no smoke without fire.

“Jen is being very coy right now,” says an insider close to the 52 year old, who’s railed at being labelled ‘poor Jen’ in the past because of her repeated break-ups.

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“All she’ll say is that they’ve been hanging out from time to time, but that it’s all purely platonic at this stage. They have their dogs to bond over, plus a few friends in common from back in the day. It’s a been real boost to her ego that he’s the one pursuing this friendship, after messing with her head when they were a proper item. She feels like they have unfinished business, and this gives her the chance for closure.”

Despite the 43-year-old singer’s colourful dating history – he’d already been involved with a series of famous faces before meeting Jen, including Taylor Swift and Jessica Simpson – many fans believed he’d finally turned a corner when they got together. But it wasn’t meant to be, with John later blaming their eight-year age gap for the split, as well as saying he hadn’t been ready to settle down.

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Jen, of course, went on to marry Justin Theroux, before they split in 2018. But our insider says she’s never quite found chemistry like she and John shared. And while she’s keeping her wits about her, she’s not against seeing where things go.

“John’s a lot more mature now, and still has that charm that Jen found so alluring in the first place,” we’re told. “Right now, there’s no expectation on either side, but the word is that they’re both excited to meet up and see if the spark is still there. She’s very mindful about how non-committal he is, but right now she’s just having fun and that’s what matters.”

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