2006

John Mayer

December 31

Stepping Out with Jessica Simpson

New Year's Eve marks the unofficial coming out party for Jessica Simpson (right) and Mayer. But the love-connection doesn't sit well with some of Mayer's longtime supporters (What's an East Coast intellectual doing with Ms. Chicken-or-Fish?) "We had a blast that night," he tells Entertainment Weekly. "Some of my fans have been a little upset at me." Still, Simpson begins tagging along on Mayer's tour, and Mayer tells Ryan Seacrest at the Grammy Awards – in Japanese – "She's a lovely woman and I'm glad to be with her."

2007

John Mayer

May 18

Breaking Up with Jessica Simpson

After months of together-time (including romantic trips to Australia and Rome), Mayer and Simpson break up – but remain in frequent email contact. They briefly reunite days later, but split for good in early June. Although both keep mum on the parting, Simpson admits to In Style, "I've had my heart broken since my divorce."

John Mayer

October

Friday Night Lovin'

After briefly spending time with Cameron Diaz, Mayer steps out with Friday Night Lights cheerleader Minka Kelly (right). The two refuse to speak publicly about their romance, but certainly log plenty of frequent flyer miles to be together: brunch in Austin, Texas, shopping in Santa Monica and courtside at a New York Knicks basketball game. They quietly split in January 2008.

2008

John Mayer

Spring

John & Jen's Hot Romance

While shooting the movie Marley & Me with Owen Wilson in Miami, Jennifer Aniston, 39, has an intimate lunch with Mayer, 30. The two stars spend the entire weekend together, where paparazzi snap photos of them embracing on a Miami beach. Although the pair is inseparable for months, their romance fizzles in August.

Photo Credits

BIOGRAPHY (top to bottom): INF; Mike Hensen/AP; James Devaney/WireImage; Fame

Edited by Mai Dinh, Janet Murphy