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If we are using the optional flanking rules, i do not think a player can get advantage from a Dancing Sword, as it is not a character, but will the Dancing Sword get advantage on attacks when flanking WITH another character?

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No to both, unless you get liberal with "allies", then yes to both

Flanking requires:

When a creature and at least one of its allies are adjacent to an enemy and on opposite sides or corners of the enemy's space, they flank that enemy, and each of them has advantage on melee attack rolls against that enemy.

When a creature is where it already falls down, because the Dancing Sword is not a creature. But you might be in luck if you want to stretch the RAW writing of the quote, because it requires 'one creature' and 'allies', and allies are not specifically mentioned as creatures.

So if you can convince your DM that the Dancing Sword is one of your player character's allies, you get the following ruling:

When Bob the Fighter and his Dancing Sword are adjacent to an enemy and on opposite sides or corners of the enemy's space, they flank that enemy, and each of them has advantage on melee attack rolls against that enemy.

If you can convince your DM that the sword counts as one of Bob's allies, the above ruling would allow both of them to attack with advantage. Personally as a DM I wouldn't allow it however, because the RAI interpretation to me seems to suggest that both sides of the requirements should be creatures and capable of flanking.

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    \$\begingroup\$ FWIW, it makes sense in-game that flanking with a Dancing Sword would work. The sword is attacking the enemy on one side, while the user of the sword is on the other. The enemy can realistically only defend against one source of attack at a time. So RAW you're correct, but as a DM I would probably allow it. \$\endgroup\$ – TheLittlePeace Jan 17 at 15:28
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    \$\begingroup\$ @TheLittlePeace That is true, but the same argument could be made for things like the Spiritual Weapon spell. And I don't think, from a balance point of view, that the weapon should be "you have advantage on all enemies in melee range at all times if flanking rules are used, because you can provide your own flanking bonus" \$\endgroup\$ – Theik Jan 17 at 15:31

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