John Mayer has dated countless women in the past, but the most random and loveable pairing came in the form of John Mayer and Jennifer Aniston.
That’s because they became the ultimate “it” couple when they dated from 2014 to 2016.
Their quirky ways and their oozing confidence seemed to win over those at home, and it just heightened Katy’s own belief that she has a thing for bad boys.
John Mayer’s relationship with Jessica Simpson proved to be a turning point for the artist.
The couple found their way to each other after Simpson’s marriage to Nick Lachey broke down, and they seemed like the most adorable pairing.
It’s not known how these two stars came to meet each other, or why they ultimately decided to part ways, but it’s been suggested that they had a deep and intense relationship.