general | March 10, 2026

Was Jennifer Aniston’s new silver Bentley originally a gift for John Mayer?

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I remember hearing that John Mayer gave Jennifer Aniston one of his guy-style Rolexes and that she wore it proudly ,even sporting it after they broke up for the second time. They got together again after that, although it’s hard to tell how long it lasted.

Now that Jennifer and John are over again for good maybe, she’s been seen out driving a silver Bentley – that she reportedly bought for him. So he gave her an expensive watch and she bought him a Bentley? I wasn’t able to semi-confirm this news at all, and this is the first I’ve heard that she bought him a Bentley. Those cars cost over a quarter million, so I’d like to think she bought the thing for herself and not her hot and cold overly talkative lover. This news is in Star Magazine anyway, so the only true part could be the fact that she’s driving a Bentley.

Nothing says revenge like a brand-new Bentley! Jennifer Aniston has been cruising around in the $350,000 ride, but she didn’t get the sexy toy for herself – it was meant as a gift for her off-again ex, John Mayer! “Jen really wanted to knock John’s socks off with this car,” an insider tells Star. “Unfortunately, they broke up soon after she ordered it.” Jen didn’t let the expensive purchase go to waste. “She got back at John by keeping it for herself!” dishes the insider.

[From Star Magazine, print edition, December 14, 2009]

Yeah, all Star has is a timeline and Aniston in a new Bentley. It’s a nice car I guess, but it kind of seems like an old person car to me. There’s something kind of stodgy about the car, but I don’t like BMWs either and they have similar lines. I also think Louis Vuitton purses are ugly, so what do I know. Just because something is really expensive and luxurious doesn’t mean that everyone will necessarily covet it.

In related Jennifer Aniston news, she was served with legal papers outside the launch of her trainer’s new yoga DVD in LA last night. Photo agency Pacific Coast News reports that she was summoned to be a witness in a lawsuit against her agent, Todd Shemarya, who “is being sued by his former assistant Heather Devlin in a sexual harassment case.” That must have sucked to get served outside after a nice time out with friends. Also at the DVD launch were Courtney Cox, Ricki Lake, Josh Groban and Faye Resnick.

A car similar to Aniston’s new silver Bentley. Photo credit: LSDSL on Wikimedia.
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Photos outside Aniston’s yoga DVD launch credit: Josephine Santos, PacificCoastNews.com. Other photos are from 11/30/09 at LAX and are credit: Fame Pictures