Love means never having to say you're sorry.
If a single line of speech can be iconic, then this is as close to iconic as a quote from a movie can get. The line is actually used twice in the movie; Oliver has some anger issues and when he apologizes to Jenny for his behavior, this is what she tells him. What she means is that when you love a person, you can behave badly sometimes, but the behavior won't be held against you. Jenny knows that he loves her and therefore does not see the behavior as Oliver, but as an isolated incident that she can completely understand and love as part of him.
When Oliver uses the same phrase towards his father, it is almost as a sign of his forgiveness. The two have been estranged because his father disapproves of Oliver and Jenny's marriage, but when help is needed, he arrives to help, putting their estrangement aside. By telling him that he does not need to say sorry, Oliver is telling him that he understands that his father loves him and that their relationship can be repaired because the love between them never went away.
Oliver : He, what makes you so sure I went to prep school?
Jenny : You look stupid and rich.
Oliver : Actually I'm smart and poor.
Jenny : Uh-uh, I'm smart and poor.
Oliver : What makes you so smart?
Jenny : I wouldn't go for coffee with you.
Oliver : Yeah, well, I wouldn't ask you.
Jenny : That's what makes you stupid.
The conversation between Oliver and Jenny is extremely revealing on many different levels. Firstly it addresses the differences between their backgrounds and situations, in that Jenny points out his wealthy background, the fact that he has been to a private prep school, and the fact that he looks preppy. Similarly she brings up her own working class roots at the same time.
Throughout the film it seems to be Oliver's family who make judgements based on appearances and assumptions, but Jenny's comments to Oliver show that it is not just the Barretts that do this. She assumes because of Oliver's appearance that he is rich, and that he is stupid; it does not occur to her that he got into Harvard on his own merits. In this way she and his family are not so very different after all.
There is also an element of flirtatiousness in this conversation that shows how much chemistry there is between the two from their very first meeting. Jenny's obvious quick-wit is extremely attractive to Oliver and the speed of her ripostes also shows the confidence that she has in herself, and the confidence she has in her ability to attract him.
What can you say about a twenty-five year old girl who died? That she was beautiful and brilliant? That she loved Mozart and Bach, the Beatles and me?
Oliver is referencing Jenny's death, and also pointing out that a life that ends at twenty five is not a whole life. Usually an obituary or a eulogy will tell of a long life well lived, of a career, years of service to a job, or a family, or an organization. Jenny did not have this and so the only things that he can say about her are the things that he loved the most about her. This also emphasizes the very young age at which she has passed.
