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Because you still have the same expectations about how music should be structured the second time you listen to it. But the effect wears off after some time. Try playing it 20 times on repeat. It won't do it anymore. But that's mostly temporary, if you come back to it after a while it should work again.

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I don't think it's about expectations at all. For me it's about the state of mind I'm in when I listen to it, same song will or won't give me goosebumps based on where my head is at even if I've heard it hundreds of times.

That's a different effect. There are different reasons why you react to music. You can have a strong emotional reaction for example because it was played during a key moment of a movie you really liked, or while someone broke up with you, and then this feeling is forever fused to a song. And recalled through it. But it is well understood that music in general connects with us by meeting and breaking expectations we have about music.

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