Hale’s superior seemed (unwilling, unwillingly) to ask anyone to cross enemy lines.

the answer is unwilling

Nathan Hale was a young man who had every prospect for a happy and fulfilling life. He was very well educated for his day — a Yale graduate in an era when very few went to college. Although there are many contemporary accounts regarding his appearance and personality, no negative statements have been recorded; indeed, he was vividly remembered and admired by his acquaintances — longer than 60 years after his death.and Both men and women commented on his striking appearance. He had fair skin and hair, light blue eyes and stood just under six feet tall. No wonder it was said that all the girls in New Haven were in love with him. Nathan's love of sports included wrestling, football and broadjumping (stakes marking one of his record-breaking broad jumps are said to have stood on the New Haven Green for many years).  

and that he was kind, gentle, religious, athletic, intelligent, good looking and as one contemporary testified, "the idol of all his acquaintances.

thanks