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Mayer and the 9-1-1 actress sparked a romance in 2002. Though their relationship was reportedly brief, it's long been rumored that JLH inspired Mayer's hit song, "Your Body Is a Wonderland."
The 7-time Grammy winner went on to date the pop-country singer for almost a year, starting in 2006. Years later, Mayer told Playboy, "Yeah, that girl is like crack cocaine to me. Sexually it was crazy. That's all I'll say. It was like napalm, sexual napalm." He later admitted that he regrets his comments.
After calling it quits with Simpson in 2007, Mayer was romantically linked to the Bad Teacher actress.
That same year, the singer-songwriter was photographed getting flirty at a basketball game with the actress.
In 2008, Mayer started dating the Friends star. Their on-again, off-again romance officially came to an end in 2009, but Mayer later admitted he wasn't over it. "I've never really gotten over it," he told Rolling Stone in 2012. "It was one of the worst times of my life."
In 2009, Mayer took to Twitter to share that he wanted to work with the music superstar. The duo later collaborated on the song "Half of My Heart," which they also performed together on several occasions. During this time, Swift and Mayer reportedly started a romance, which may have served as the inspiration for T. Swift's song, "Dear John."
John and the pop star had a roller coaster of a relationship, which started in the summer of 2012. The two artists spent the next few years having an on-off relationship, with Perry later moving on to her current beau, Orlando Bloom.
Mayer and the "Without Me" singer have been getting flirty on social media recently following her split from G-Eazy. From FaceTime sessions to flirty Instagram comments, these two are sparking romance rumors! Halsey later shut down any rumors with a tweet that said, "I just had a ground breaking idea. What if...we let female artists...have friends...without assuming that they are sleeping together? I know I know. It's like, completely ambitious but like, imagine if we like, tried ?"