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The Question and Answer section for David Copperfield is a great resource to ask questions, find answers, and discuss the novel.
I believe his desire to court Miss. Shepherd was the first loss. The second would have been Miss. Larkins engagement. I see no evidence that one of these losses was the "greatest loss".
What chapters are you referring to?
Steerforth's words foreshadow what will come. He is morally lacking.... and even now, he knows that he will alienate David at some point in the future. Steerforths seduction on Miss Emily will sever their friendship.
