The heart was made to be broken, so why not give it an extra push? I was very tempted to make this playlist just a loop of Jeremy Jordan singing Don't Speak (my a-b-s-o-l-u-t-e favourite version, if not the only correct way to sing it, including passive aggressively hushing the band). But there are just so many amazing bittersweet tunes, it would be a shame to not mention at least one or two of them....

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