... and the songs they inspired.
Swift dated Joe Jonas of the Jonas Brothers trio in 2008. After several months, he left her for his "Lovebug" video co-star, Camilla Belle.
The song: "Forever and Always"
The country star ended up dating her "You Belong With Me" video co-star, Lucas Till. According to Till, the relationship didn't last because he "just really liked her as a friend."
Swift met Lautner while filming the movie "Valentine's Day." Her song "Back to December" is rumored to be about their breakup.
Swift dated fellow musician John Mayer briefly in 2010. Eleven years her senior, it came as no surprise when he called it quits only after a month. Her song, "Dear John" is thought to be about Mayer, although Swift says that's "presumptuous."
Swift moved on to "Glee" actor Cory Monteith. The two tried to keep their relationship under wraps, but they couldn't fool us!
Alas, yet another older celebrity breaks Swift's heart. This time, leave it to Jake Gyllenhaal. It's rumored that many of the songs featured on her new album "Red" are inspired by the split, especially "All Too Well."
Swift reportedly had a quick fling in 2011 with Zac Efron.
Their summer romance fizzled out after Taylor hit the road to promote her new album.
Swift's latest heartbreak comes shortly after the new year. She and the One Direction frontman began dating last November.