5. Jesse James & Kat Von D. I didn't buy them as a couple to begin with. Jesse James and Kat Von D had kind of a whirlwind romance after Jesse's divorce from Sandra Bullock. He was a constant fixture on Kat's reality show and the two became engaged in January of 2011. That only lasted until July when the two called it quits right before Kat's new season was set to air. They got back together in August before decided to end it for reals in September. But seriously, they were kinda a bizarre couple. No idea how they made it work for as long as they did.