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Kirito and Heathcliff were arguing over Asuna, but the duel isn't really about her, but rather about Kirito. Win or lose so will they still be together and Asuna will still be in the guild. All the duel decides is if she will take a short break from the guild duties or if Kirito will have to join it.
As for trusting a maverick like Kirito in a serious battle, so does he already fight with them during the floor Boss fights. The only change is that he will now do so while wearing their guild tag.
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