You and Damon have been best friends since you were kids. Elena broke up with him and left state for some guy named Onyx. (Just go with it). Damon believes love isn't worth it. But you try proving otherwise. He slowly starts believing you. He's been in love with you, but he doesn't even know it.

You're both sitting outside, near a river

Damon: I've been in love....It's painful, pointless, and overrated.