A Massive Squid/Octopus

I am introducing a friend of mine Tim to others, like the announcer on a game show, who is supposed to figure out some type of riddle or problem

It becomes obvious to me that he's not going to work it out, so I decide to fix it for him

There is a massive squid or octopus that is so big/massive/huge that it is literally dragging a resort filled with people on its back

It is trying to get through into a body of water, but there are poles on either side of the causeway preventing it from getting through, with the world full of people is is carrying on its back

The riddle/puzzle has something to do with helping the squid/Octopus enter

I realise I can remove the poles temporarily to let it through and then put it back once it's through

I barely get half of one side of the poles down before the squid/octopus pushes its way through, taking me along with it (underneath it)

I free myself from underneath and gently guide it into the waters

It feels like it urgently needed to get into these waters or there was a problem

The waters are a beautiful fluorescent type of green/blue

I am amazed at how beautiful the waters are

As is disappears into the water I see a couple in the waters

A woman and her partner

I'm not sure who the man is and I don't really care, but I feel like I know the woman and I'm not at all happy to see her

I get a overwhelmingly unhappy and angry feeling like "What is she doing here? She's not supposed to be here"

It feels like nobody is meant to be in this water, surely not her and especially not whoever the man is she has with her

This woman keeps turning up in my dreams/visions and things of the sort

I don't know who she is, but I'm starting to honestly feel hatred towards her because I can't get rid of her and she is always places she shouldn't be

She is like some type of unwelcome pest

Not evil, because she doesn't even seem to be real

She feels like some type of imitation that is placed intentionally to annoy, by something using her intentionally to annoy

The last thing that is interesting to me about letting this massive squid/octopus carrying a world of people on its back, into a luminous pool of water, is that it feels like all of it combined ....

Is an eye