Christina Applegate and Brad Pitt Before 1989 MTV Movie Awards Disaster

Brad Pitt and Christina Applegate could have been the ‘it’ couple of the late 1980s. They began dating when Pitt was 25 and Applegate was 17, but they never stood a chance when things went downhill on the very first date. This was at the 1989 MTV awards show, and after arriving at the venue together, Christina left Pitt’s side unannounced in the arms of another man.

Applegate never publicly told anyone who she left with, abandoning Pitt during the middle of their date. But some fans speculate it might really be Sebastian Bach, who already claims to be that man who broke Pitt’s heart and date.