John Mayer

In the early 2000s, John Mayer dated his fellow chart-climber, Vanessa Carlton. However, they called it quits in 2002, and shortly after, he was linked to Jennifer Love Hewitt. Unfortunately, they didn’t last long together. He then began seeing Jessica Simpson in 2006, but when he referred to her as “sexual napalm” in a 2010 interview, it was the final straw that ended their on-off relationship.

Some of his other flings were Jennifer Aniston, Cameron Diaz, Rashida Jones, Scheana Marie, and Taylor Swift, who he dated back in 2009 when she was still 19 years old and John was 32. He was also briefly linked to Kim Kardashian but it was just a baseless rumor. His only long-term girlfriend was Katy Perry, whom he dated from 2012 to 2016. They had a collaborative song together titled, Who You Love. John even dedicated his lovesick song, Still Feel like Your Man to Katy, saying that this was his ‘only’ relationship. Well, it was a good thing he never married any of these girls, otherwise, he would have spent a ton on lawyer fees.