The unexpected
A Caretaker is employed to look after the ill person. Winston is strong enough to manage his work and also drill the doctors who are under him.
So a friend, according to mental health, having good positive friends and spending time with them is really important and that changes our outlook for better.
Winston knows that but he always ignored it thinking he was doing good without friends. But is he really good? Then why can't he smile and mingle with people? Is that the reason he is cold and unapproachable? Is it why none dares to be friendly or strike a general conversation?
Winston didn't think about a question but asked, "Then why should it be a woman? Why can't it be a man? A man can also be a good friend."