1-what does 'watches of night' mean?
2- rolling eyes emoticon means?
Could you please provide the context where you saw/read/heard that phrase?
Do you not roll your eyes in your culture? It expresses amused exasperation.
I'm not a teacher, but I write for a living. Please don't ask me about 2nd conditionals, but I'm a safe bet for what reads well in (American) English.