In general, you'd rather learn about someone's ______ breakup
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Worst. Not out of any kind of schadenfreude, but because there's something informative about extreme cases, I think.
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It all depends. If there is a romantic interest, then last, as development and growth in one's ability to interact with other beings should have made progress over time compared to some young mistake. If no romantic interest, worst, as it's all just about the joy of story-telling