What personal lesson in "American History" had Elena experienced deeply?

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The personal lesson that Elena learned is that there are different levels of outsiders, and she  would be considered beneath Eugene by his own family.

For Elena, a personal heartbreak converges with a national crisis.  She feels like an outsider, not an American.  When she meets Eugene, she sees her chance at happiness.  He is an outsider like she is, because he is smart and has a strong Southern accent.

The kids at school called him “the hick” and made fun of the way he talked. I knew I was his only friend so far, and I liked that, though I felt sad for him sometimes.

Although Elena feels like she is making progress getting to know Eugene and she has a chance because the other kids consider him an outsider, she learns that this is not really the case.  This lesson is learned symbolically and literally with the assassination of President Kennedy.  Unable to feel as she knows she should feel, Elena wallows in her own grief.  She wants to mourn the president, but she mourns the loss of her own adolescent love. 

That night, I lay in my bed trying to feel the right thing for our dead President. But the tears that came up from a deep source inside me were strictly for me.

She feels even more like an outcast and outsider, more isolated and alone, because of the self-loathing of not grieving the national loss with everyone else.

The contrast of everyday life, and the small matters of teenage love with the large ones of national pain demonstrate how Kennedy’s death touched the lives of every American in different ways.  Elena did grieve, but she was grieving for herself as well.

The moral of the story is that sometimes the outsider is not the one you think.  Kennedy was not the average president.  In many ways, he represented an outsider and immigrant like Elena.  He would have understood her pain and isolation more than she would have realized.

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