According to Miley Cyrus' autobiography, "Miles To Go," she first met Nick Jonas at the Elizabeth Glaser Pediatric AIDS Foundation charity benefit on June 11, 2006 (per PopSugar). By that summer, the two would be spotted together with Jonas' arm around Cyrus. It was around that time the brothers appeared on "Hannah Montana."
Things got a bit more public when Cyrus joined the Jonas Brothers on stage at the Teen Choice Awards to promote the Best of Both Worlds Tour, which started in October 2007. It was while they were on that tour that the two first split. "Prince Charming and I broke up on December 19, 2007. The hardest day ever," Cyrus wrote in her book. "My life felt like it had ground to a halt, but the rest of the world kept right on rolling. I was on tour. People were counting on me, but my head — no, my heart — was dizzy."
It was tense between the two as they completed the tour and promoted the 3D concert film that went with it. "I bawled for a month straight," Cyrus told Seventeen of the breakup (per E! News). "I was so sad. I just went into this weird funk. And I dyed my hair black."
