Leslie doesn't fit in and gets bullied a lot by his classmates, so Jess gets frustrated with her. Because of his feelings about Leslie, he couldn't sleep because of worrying about it too much.
The answer to this is your hair. I just looked it up and thats what most sites are saying
He is scared of the ultimate duties he will have from being an adult and the regret for what he had done as a kid.
Shroud
/SHroud/
Learn to pronounce
verb
past tense: shrouded; past participle: shrouded
1.
wrap or dress (a body) in a shroud for burial.
2.
cover or envelop so as to conceal from view.
"mountains shrouded by cloud"