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- In 2006, John Mayer began dating pop singer Jessica Simpson. The couple reportedly met at a Grammy Awards party, leading to an on-off relationship that lasted until 2007. Jessica Simpson is a multi-platinum pop singer, known for hits like Irresistible and I Wanna Love You Forever.
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Jul 7, 2023 · Jessica Simpson John Mayer and Jessica Simpson (Shutterstock) After her marriage to Nick Lachey ended in 2006, Jessica’s first high-profile relationship was with John. The couple...
Aug 1, 2021 · Jessica Simpson had seemingly moved on from John Mayer in the fall of 2007 after she began dating NFL star, Tony Romo. According to Simpon's memoir, Mayer used to text and/or email the "I Wanna Love You Forever" singer while she was with Romo — who had always been suspicious of the former couple's relationship — however, Simpson wrote that ...
- Olivia Jakiel
- John Mayer’s Dating History: Jessica Simpson, Jennifer Aniston, Katy Perry and More. John Mayer has been unlucky in love — and he’ll be the first to admit that he’s partially to blame.
- John Mayer’s Dating History: Jessica Simpson, Jennifer Aniston, Katy Perry and More. John Mayer has been unlucky in love — and he’ll be the first to admit that he’s partially to blame.
- Jennifer Love Hewitt. The musician and the I Know What You Did Last Summer actress dated in 2002, and it was long rumored that he wrote “Your Body Is a Wonderland” about her.
- Jessica Simpson. The pair dated from 2006 to 2007, but it wasn’t until the aforementioned 2010 Playboy interview that Mayer spoke publicly about his attraction to the “With You” singer.
- Katy Perry. Katy Perry and John dated for two years on-and-off before the pair eventually split in 2014, and the pop singer moved on with actor Orlando Bloom.
- Jennifer Aniston. Back in 2008, actress Jennifer Aniston began dating John after the two met at an Oscars party. However, their relationship lasted less than a year as the singer disclosed in the infamous Playboy interview that he broke up with the Friends star, hinting that their eight-year age gap may have been a factor.
- Taylor Swift. While Taylor Swift infamously never discloses what famous exes are the inspiration for her songs, it is widely believed "Dear John" (from her third studio album Speak Now) is about her short-lived romance with the singer while the two dated from December 2009 until February 2010.
- Jessica Simpson. Following her split with first husband Nick Lachey, Jessica Simpson began dating John in 2005, but their on-and-off romance ended two years later.
Jan 22, 2020 · Published on January 22, 2020 01:15PM EST. In her upcoming memoir Open Book, Jessica Simpson writes candidly about what she learned about herself from her relationships, including her romance...
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- Liz McNeil
Jul 7, 2023 · Jessica Simpson. His rockstar mindset quickly caught up with him, however, when he came under fire for a series of now-infamous tell-all interviews about his A-list relationships — including the...
Apr 2, 2020 · Maria Pasquini. Published on April 2, 2020 07:00PM EDT. Photo: Bravo. John Mayer has responded to ex-girlfriend Jessica Simpson ’s recent memoir Open Book, in which she candidly...
