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D&D 5E Tavern Brawler + Rope/Hook... reach grapple?

I would use the net rules rather than the grapple rules here. I'd let you pull someone in a net too.

Do recall grappling requires a free hand. I don't think it is unreasonable to require that hand to be able to reach the target. Tavern Brawler doesn't remove that requirement.
 
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The kuo-toa use a pincer staff that lets them grapple at 10'. Here's how I ran it:

If the grapple succeeds, the kuo-toa with the staff and the target cannot attack each other in melee. However, the target can still melee adjacent squares as normal. The kuo-toa can push/pull the target with an opposed strength check.

Basically, one of the kuo-toa would try to catch a PC with the staff, then pull the PC away from allies to a floor hazard or a position where other kuo-toa could attack.

The PC grappled by the staff can three options:
1- Try to escape by rolling Str(Athletics) or Dex(Acrobatics) vs DC
2- Try to grapple the kuo-toa (success means that you have a firm hold on the staff and good footing), after which you can push/pull the kuo-toa with an opposed Str check.

Of course, in case (2) the kuo-toa would have the option of simply dropping the staff, in which case neither party is grappled any more.

So for the rope/hook combo, I would allow some similar mechanic and reward the player for a clever idea for an improvised weapon.
 

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