This moment for me is the best Season 4 moment for Damon Salvatore. Because he doing what he does best. He is being completely honest, brutally honest. Not only with Elena, but with himself. He is literally just screaming out all of the reasons why he is insecure about their relationship and why he feels that he is unworthy of her love, of love at all. He is finally coming out with all of the insecurities and worries and hurts that have been plaguing him all season. He is letting them hang out there in the air for her to see.
All cathartic feelings exposed, he is laying himself bare to her. He is saying “THIS IS ME. THIS IS WHO I AM. And I get it if you can’t love me. If you can’t love that.” And as much as it hurts to see him feeling this way about himself and talking this way about himself, it is what he needed. He NEEDED to get these feelings and worries out of his body and mind and soul, to rid himself of them. He needed to allow Elena in. And the only way to do that was for him to honestly spell out to her all the reasons he feels he is unworthy, irredeemable, undeserving. For her to hear all these reasons, and then afterwards to still tell him I LOVE YOU DAMON… it meant everything to him.
He owned it. This moment was so DAMON. Angry because he is passionate. Consumed by wanting to be consumed. Wanting love so badly but not daring to hope for it. Self-deprecating before he can be put down by someone else. He has come so far but he can’t see it yet. BUT SHE CAN. And that is why I love this moment. Because he exposed all of his greatest fears about himself… held nothing back. He was brave yet vulnerable, determined yet unsure. That is Damon. An enigma. A contradiction. Our prince of darkness.