Damon's relationship with Matt is interesting in that, aside from Stefan, Matt is the only other male character present in the books that isn't on the opposing side. Matt is also the only one who stands up to Damon and calls him on his behavior in a direct, human way (Dark Reunion). Damon seems to develop a guarded respect for Matt after this confrontation, perhaps admiring the courage it took to stand up to someone like Damon. Although Matt and Damon don't communicate much before or after their confrontation, they seem to have an uneasy relationship of acquaintance going by the end of Dark Reunion.