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I haven't really watched Buffy before, but I can try to help a little:
1. Whitney Houston - "I Learned From The Best" (It's about a person who now knows how to break people's hearts because her former lover broke hers, then she does the same thing to him.)
2. Toni Braxton - "How Could An Angel Break My Heart" (Beautiful song with strings and Kenny G.)
3. Christina Aguilera - "Walk Away"
4. Evanescence - "My Immortal (Band Version)"
5. Pink (with Steven Tyler) - "Misery"
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