Vanessa Carlton: 2002
Back in the early 2000s, John Mayer dated the beautiful Vanessa Carlton. The pair met as they started their musical careers and paved their way to stardom! Carlton is best known for her hit song A Thousand Miles. Their whirlwind romance wasn’t meant to be.
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Their short-lived relationship didn’t even last a full year before the singing duo called it quits in 2002. John set his sights on the stunning actress Jennifer Love Hewitt. Nowadays, Carlton is married to John McCauley. The couple couldn’t be happier and in 2015, they had a baby girl named Sidney.