Bristol Palin and Levi Johnston
It read like an Alaskan fairytale. Levi, Wasilla High School's star hockey player, had dated Bristol, the eldest daughter of the state's governor, since freshman year. His love ran so deep that after losing a promise ring (while hunting caribou), he tattooed her name on his finger. Then she got pregnant, and the Republican Party announced that the teen paramours would soon marry. Then vice-presidential candidate Sarah Palin and presidential candidate John McCain lost the election, and the pair broke off their engagement in March 2009, just three months after their son Tripp was born. Bristol toured Alaska advocating abstinence, and her hunky baby daddy posed for Playgirl. Despite their troubles, they both remain committed to raising Tripp together. "I think [Levi] needs to know that he is loved," Sarah Palin told Oprah Winfrey. "He has the most beautiful child, and this can all work out for good. It really can."