After their breakup in 2007, John Mayer eventually started reaching out to Jessica again in 2009 when she was dating Tony Romo. Tony found an email John had sent Jessica, and it was over right then and there.
She said: “Tony accused me of seeing John behind his back. I hadn’t cheated on Tony at all, but I could not lie and say I hadn’t even seen him. Tony didn’t believe that for a second. And within that second, he broke up with me right there. Two years gone, with an email.”