This is an absolute struggle. Most of the songs that are coming to mind would be difficult, if not impossible, to write an adequate sequel for.
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Originally posted by Temporal
Ehhhh. I'd want more allusion that "Hey, this is a sequel" than what's between HG/LK. You want to have a standalone song, sure, but for the purpose of the challenge, there should be a stronger between the two songs in question. There shouldn't be question or doubt.
The love interest in LK/HG is too ambiguous me thinks, in PBP and BOY there's a much clearer development and direction because both songs are about her father, someone more specific. Does that help? 
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How is Kelly calling PBP "BOY 2.0" any different from Taylor spelling out the title "Forever & Always" in a hidden message in the lyrics of "Last Kiss," or using a lyric from "Superman" as the hidden message to "Dear John"? Both make it clear that the songs are about the same subject, and are therefore "sequels."
Would "White Horse" be an acceptable example of a sequel to "Love Story" because of the common fairytale imagery and the shift from "I'll be the princess" to "I'm not your princess"?