Season 2: Aaron Buerge
Winner: Helene Eksterowicz
What happened? Aaron and Helene got engaged during The Bachelor Season 2 finale, but sadly they broke things off shortly after the season aired. And guys? It wasn't pretty — unlike Helene's 2-carat engagement ring. "It felt like a bomb dropped," girlfriend told People at the time. "I said, 'I feel very deceived by you. You've told me every single day that you love me, and now this is it?'"