Suppose an ettercap sneaks up on Bob the Barbarian whom is trailing his group and attacks him with a web garrote, inflicting Bob with the Grappled condition. Normally this is to the ettercap's advantage, but Bob is fine with grappling and feels the scenario is closer to the ettercap being trapped with him.
In order to ensure that this sneaky enemy can't escape, Bob wants to turn around and grapple the ettercap, to force it to hold still while Bob's allies rain pain on it from afar.
Can Bob do this without breaking the original grapple? If so, are both creatures considered to have the Grappled condition and thus have a speed of 0?
Best Answer
Yes, you can try to grapple an enemy who is grappling you.
The rules for grappling are...
PHB195
The effect of a Grapple is...
PHB290
There's nothing in here that prevents you from counter-grappling, as long as you have a free hand and can reach your target. In which case you are both subjected to the Grappled condition, and now neither one of you can move without breaking the grapple first.