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Love's Labour's Lost. As the title implies, notwithstanding their "labour" at getting together, at the end of the play nobody gets married to anybody else. The play itself recognizes that this was totally unconventional for a comedy. "Berowne: Our wooing doth not end like an old play: Jack hath not Jill". Contrast the much more conventional Midsummer Night's Dream: "Jack shall have Jill; nought shall go ill; the man shall have his mare again, and all shall be well."

Another Shakespeare play which was a departure from the conventional was Troilus and Cressida. To this day, people argue over whether it is a comedy or a tragedy or something totally different.

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Q: What was Shakespeare's groundbreaking play?
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