Katy Perry

As much as John Mayer is known for being one of the music industry’s most talented musicians, he’s also garnered quite the reputation as a playboy. After all, the “Gravity” singer’s long list of flings, hook-ups, and on-and-off relationships includes some of Hollywood’s most high-profile female stars.

While Mayer dated a large number of women in the early 2000s, he actually hasn’t officially dated anyone in the public eye since his relationship with Katy Perry fizzled out in the mid-2010s. He’s also tried to correct some of the more negative assumptions about him a number of times since then. “I think a lot of people’s last impression of me is outdated,” he told The New York Times in a 2017 interview. “I’ve inherited a younger man’s reputation. You can even break ‘bad boy’ into good bad boy and bad bad boy — I somehow managed to become a bad version of a bad boy.”

In 2018, he was spotted exchanging flirty messages on social media with musician Halsey, per E! News, but Halsey quickly shut down speculation about their relationship status. “I just had a ground breaking idea,” they tweeted at the time. “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?”

Most recently, Mayer has been spotted out with 22-year-old actor Kiernan Shipka more than once, sparking dating rumors, though nothing has been confirmed, and reps for both stars did not immediately respond to POPSUGAR’s request for comment. Ahead, relive Mayer’s dating history over the years.

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