John Mayer: December 2009 – February 2010

One of the most widely recognized breakups in Taylor Swift's dating history involved John Mayer. Some attribute their separation to a notable age gap, while others believe things took a complicated turn when Taylor penned the song "Dear John" about their relationship.

The song holds a special place in the hearts of Swifties, even though it carries a sad and melancholy tone. John Mayer's reaction to the song wasn't particularly positive, and rumors swirled that his song, "Paper Doll," might be a response to Taylor, though he has neither confirmed nor denied this speculation.

Advertisement