aggienaut | Near-synonyms

I have a deep philosophical question for you. It may cause some soul-searching and perhaps an identity crisis or two.

My recently former flatmate Eric, a native of Taiwan, liked to ask me questions about the difference between near synonyms, like "wreck" and "ruin" or "burst" and "explode." I found it rather entertaining to try to hash out the subtle differences.

I felt I was having difficulty, however, adequately describing the differences between "jerk," "asshole," and "dick." I feel like there's something about it that causes one's boss to be more likely an "asshole" than a mere "jerk," and I think "dick" intends a more intentional inconveniencing of others, but I'm curious to hear your thoughts!