John Mayer has been unlucky in love — and he’ll be the first to admit that he’s partially to blame.
In the early days of his career, the “Gravity” singer was riding high as he scored dates with everyone from Jennifer Love Hewitt to Jessica Simpson.
After his romance with Simpson fizzled in 2010, Mayer subsequently dated Jennifer Aniston, Taylor Swift and Katy Perry, romances that made headlines — and songs. Fans have long theorized that Swift has written a handful of tracks about Mayer, including Speak Now‘s “Dear John,” Midnights‘ “Would’ve, Could’ve, Should’ve” and more, while Mayer’s “Paper Doll” is rumored to be about the “Anti-Hero” artist. Mayer also admitted to writing music about Perry.
In October 2025, a source exclusively confirmed that Mayer was dating influencer Kat Stickler, adding that the relationship wasn’t “serious.”
Keep scrolling to see Mayer’s A-list romances throughout the years:
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