Best of 2009

Split! The Year's Biggest Breakups

From Jessica and Tony to Jon minus Kate, it was a year of dramatic endings

JESSICA & TONY

Pals said Jessica Simpson was hoping for an engagement ring on her birthday. Instead, on the night before her 29th bash, Dallas Cowboys quarterback Tony Romo broke off his nearly two-year relationship with the singer. Sources close to the couple said her family factored into the split. "They are extremely close and when you date her, you date her family," the source said.