And then there was John Mayer. Jennifer Aniston and the “Your Body Is a Wonderland” singer dated on and off for about a year after meeting at an Oscars after-party in 2008. They split in August and Mayer held an impromptu meeting outside his New York gym to discuss their initial break up: “There’s no lying, there’s no cheating, there’s no nothing … People are different, people have different chemistry.” However, the former couple gave it another go, with Aniston bringing Mayer along as her date to the 2009 Oscars. They split shortly after.
In an interview with Rolling Stone in 2010, Mayer shared that the split was one of the hardest times he’s ever been through. “I have this weird feeling, a pride thing, for the people I’ve had relationships with … What would I be saying to Jen, who I think is f****** fantastic, if I said to her, ‘I don’t dislike you. In fact, I like you extremely well. But I have to back out of this because it doesn’t arc over the horizon. This is not where I see myself for the rest of my life, this is not my ideal destiny,'” he said.
Read Related Also: Sarah Lew and Chris Lucas tie the knot in Venice in front of celebrity guests
That same year, Mayer’s widely controversial Playboy interview came out. In it, the singer confessed to still loving Aniston, however, he appeared to take a dig at their age difference: “I’ll always be sorry that it didn’t last. In some ways I wish I could be with her. But I can’t change the fact that I need to be 32.” Despite this, the singer attended Aniston’s 50th birthday celebration in 2019.
