7 Guys Who Totally Blew It With Taylor Swift

Year: 2012

What Happened: Taylor was practically an honorary member of American royalty before the duo went their separate ways. His famous grandmother Ethel Kennedy gave her seal of approval, saying, "She's just sensational inside and out." Taylor even had a residence near the family's Cape Cod compound. She sold the Hyannis Port, MA, home for nearly $6 million in March 2013, mere months after the split and less than a year after purchasing it.