I had already completed the outlines for Discord but I let the board rest for several months before I thought of something better to include here.
We have seen Discord interact mostly with Fluttershy and to a lesser degree with Starlight, Twilight and Spike while we know very little about any interacting of him with other ponies. However, I could very well imagine for Fluttershy to encourage Discord to try to make some more friends among the ponies of Ponyville.Among those Ponies I could very well see Derpy as a potential friend for Discord. She is probably not very judgemental but rather forgiving and accepting of Discord’s being different. Moreover she might be a lot more curious and open minded rather than intimidated or annoyed by Discord’s antics.
Discord on the other hand might end up liking a Pony who is a bit chaotic and (though unintentionally) has been the reason for some chaos. Discord might very well use his powers to practice some kindness on Derpy.
This is a digitally colorized version of the pyrography