Season 14: Jake Pavelka
Winner: Vienna Girardi
What happened? Jake and Vienna were a match made in the opposite of heaven (read: Bachelor hell — a sinister place filled with flowers that aren't roses). Despite the fact that these two became engaged on The Bachelor, they broke things off in June 2010 when Jake dumped Vienna over the phone. "It was a difficult conversation on the phone," he told People. "But the relationship was headed in that direction." Jake is now dating Broadway legend Kristin Chenoweth.