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Here are the rules on falling:

At the end of a fall, a creature takes 1d6 bludgeoning damage for every 10 feet it fell, to a maximum of 20d6. The creature lands prone, unless it avoids taking damage from the fall.

One of the effects of the Enhance Ability spell is called Cat's Grace:

The target has advantage on Dexterity checks. It also doesn't take damage from falling 20 feet or less if it isn't incapacitated.

Let's say Bob is affected by Cat's Grace. Bob grapples Rick and starts dragging him forward, but then a trap opens below both Bob and Rick into a 20ft deep pit, making both of them fall down. We know Bob does not take falling damage, but what about Rick? Does Rick take the 2d6, or does he also take nothing, thanks to Bob acting as some sort of cushion?

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Yes, you (Rick) takes damage

Enhance Ability states (emphasis mine):

You touch a creature and bestow upon it a magical enhancement. Choose one of the following effects; the target gains that effect until the spell ends.

Cat's Grace. The target has advantage on Dexterity checks. It also doesn't take damage from falling 20 feet or less if it isn't incapacitated.

Cat's Grace has zero effect on Rick because it is cast on Bob and it only affects Bob.

How this works narratively is up to the DM/Player, but there is nothing in the language that confers the spell effects onto the grappled target so the grappled target still takes the damage.

How I'd narrate

I'd say that Bob and grappled Rick fall into the pit together. Bob's enhanced ability of Cat's Grace allows him to position himself to land on top of a prone and damaged Rick. His grapple is continued and things proceed. But Rick is now prone and grappled.

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    \$\begingroup\$ A cat always lands on its feet. Sometimes the cat's feet also land on you. \$\endgroup\$ – Darth Pseudonym May 8 at 18:38
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By RAW, Rick takes fall damage whether Bob likes it or not.

There is nothing I was able to find in the RAW in either Grappling or Falling that would indicate a special interaction between the rules for either, so by RAW, Rick fell 20 feet and suffers the damage accordingly.

It also states that a grappled creature two sizes larger than the grappler doesn't slow them down at all, and specifies that the grappler can "move or carry" them, but in none of these caveats does it say anything about any of this affecting fall damage. Bob could not be this kind of cushion even if he wanted to be.

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