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I liked Shirley, she was both cheerful and someone who genuinely loved Lelouch, coming to understand him in her next-to-final moments...all of which made her death especially sad, but her story always had a high probability of ending in tragedy once the Mao arc had set things in motion so I expected her fate to be bittersweet at best.
If the subplot introduced near the end of the first season had continued and she had confronted Lelouch about the letter, I expected the eventual results to be painful for both of them considering where his own path was eventually going to take him (and where it indeed did).
What could have made a difference are the circumstances under which such a meeting finally happened and in that respect I imagine that there were endless possibilities. Would she understand his goals, join him and try to help out somehow? That would have been very interesting to see. At the same time, she could also have chosen to reject his methods and stay at the school, or Lelouch would have to cut himself off from that world, willingly or otherwise, leaving Shirley as someone who would wait for him without being directly involved in the grand scheme of things.
It's hard to say what would happen in terms of specific events.
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