Christina Applegate and Brad Pitt
In 1989, Christina Applegate and Brad Pitt were dating when she was just 17 and he was a 25 year old struggling actor. While at the VMAs, Applegate actually ditched Pitt in order to meet up with Sebastian Bach, lead singer of Skid Row. When asked about the dumbest thing she ever did in an interview with Entertainment Tonight, she admitted: “One night, I ditched Brad Pitt for this other dude.”
Christine Taylor and Neil Patrick Harris
Neil Patrick Harris dated actress Christine Taylor from 1997 until 1998. He told Howard Stern: “She’s the coolest, nicest chicken ever. She’s an absolute catch, and I thought if I’m not going to feel the super sparkls with her…it probably means I’m gay.” He came out officially in 2006, saying that he is a “very content gay man.” Taylor went on to marry Ben Stiller. NPH is married to David Burtka.