dice are d600, roll low to hit/crit/effect
Step 1:

rest
-15 en
heal for 20
+5hp +3en

nightshade
-5 en
15 dmg
Step 2:

sing
-7 en
299 hit yes

is asleep (2)
+5hp +3 en

zzz
+5hp +3 en
Step 3:

sing (chill is not a move, it is an action, it cannot be attempted while asleep using sleep talk)
-7 en

faints!

is already asleep