Regina and Robin Hood
We'll say it: poor Regina. When the loss of her first love essentially propelled her into becoming the Evil Queen, it seemed like she would never find love. She believed that herself for so long, refusing to act when Tinker Bell presented her with the man she was destined to love again, Robin Hood. The two have had their fair share of low points (hello, her half-sister gave birth to his baby!), but things were finally looking up when Robin confessed his love and told Regina that she was "his future." Alas, Regina was faced with yet another unhappy ending when Robin Hood was killed by Hades in season five.