I'd say the bends are the least of its problems.

Or, the squid is having the best day ever, getting a piggy back ride from their bestest buddy whale.

Wheeee!

Squids are naturally bendy so it's not a problem for them. Humans on the other hand have many bones, and so getting the bends is much more serious.

For the squid, it's like being lifted into outer space.

depends on how much nitrogen is diffused through their bloodstream and soft tissues. for a creature living at those depths, I'd wager: not a lot.

also, nitrogen narcosis is probably not very noticeable compared to being clamped down by 20' jaws and dragged to the surface while being chewed.