Starting off where season one ended, season two opens at the Gilbert house with Uncle John mistaking Katherine for Elena. Now if, you'll remember, John is actually Elena's father, the brother of her adoptive father, who is descended from the founding Gilbert family who tried to round up the town's vampires back in the 1800s. Katherine is the one who turned Damon and Stefan into vampires way back when, a fact that Stefan would like to forget, while Damon has been searching and pining for her for these hundreds of years. Damon turned Isobel, Elena's mother, who was married to Elena's history teacher, Alaric, who came to Mystic Falls to kill Damon, who has seemingly moved on from Katherine to Elena. Problem is, Elena's in love with Stefan.
No matter how hard he tries, Damon is a Salvatore brother that just can’t catch a break. He tried being the bad seed, the one who doesn’t care, the snarky adult who doesn’t mind being hated. But behind all his antics, Damon craves acceptance and love more than human blood.
As alone as he feels, Damon isn't the only Mystic Falls male whose life sucks (pun intended - this is a vampire show, after all). In fact, season two appears to belong to these easy-on-the-eyes brooders who push away everyone around them when all they really want and need is to hug them.
