Both of them strive for love; both of them have been in unrequited love or rejected because they weren’t the person that person really wanted.
Both of them felt inadequate by their respective parents, and were actually turned away by their parent once they became vampires (although Caroline’s mother later accepted her, Damon actually spoke out for Caroline in this regard. He knows how it feels.).
I actually think their little scene in 1x01 was adorable. Plus I adore dark!ship tropes, unhealthy relationships, and obsessive personalities (girl or boy), if you couldn’t tell from my other ships. (;
I acknowledge that the ship is majorly flawed, and that Damon has raped, manipulated, and attempted to kill her and her family members/friends multiple times. That would be deplorable in this world, however this is a fictional vampire show. Different morals, different motivators.
They were my very first TVD ship, and I do think he cares for her in his own twisted way; and I don’t think I remember a time when he let someone else try to kill her right in front of him. (He has always tried it himself, no one else can. Romantic, no?)
I think their dynamic as sire and prodigy would be an interesting one to explore as well.
Here are some fics of them I enjoyed. Careful, - trigger warnings and smut ahead, and one is plenty dark.
Robbie Kay as Henry Mills in 3x10 "The New Neverland"
(…), about to bend the knee for the first time in his thousand years, and what relief will come with it. (x)