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First off let's address the formatting. All the slugs should have a period after the INT. or EXT. and not a dash. Also, no : after the character's names. And when you introduce MAN, you should just call him DAVID at that point, and instead of saying "looks to be around 34", just say DAVID (34).
Also, the first page has a lot of "we see" and "the camera" doing things. Don't direct the camera. If you want to show the staircase, say something like (since you say it's raining) "the dark staircase lights up in a flash of lightning". This tells the reader - and the director - we're seeing an empty staircase.
Also, break up the longer narratives and put a space between each shot that you envision happening separately.
As for the story, I went back and forth on it. The first problem I have is that ...
... you have David tell Ryan he "committed suicide", and then you back out of it.
Second, your premise is that Ryan gets the chance to save Cassie. Really there's no "peril" once Ryan comes back to life, since his mere appearance as being alive will save Cassie (i.e., she's not depressed or going to kill herself over anything other than Ryan leaving her).
Third, you don't fully explain why Ryan feels guilty over Donnie's death. Nothing in the story suggests that Ryan would have been at fault, and certainly not anything enough to push him towards his own suicide. All we have is David telling us that Ryan feels guilty.
Lastly, David's dialogue is way to expository. You need to find a way to get the "back story", i.e., the happenings, into the narrative rather than the dialogue. As for the whole purgatory thing, it's been done to death (no pun intended), so you need a REALLY fresh angle if you're going to write a story like this.
My advice would be to go over each character and make sure they're fully fleshed out and that their motives are clear to the reader. Again, watch the on the nose dialogue, and spend some more time breaking up - and punching up - your descriptive narratives.
This is not bad, although I was hoping for an ending with more impact. It just drizzles the way it is now.
The story is interesting, but not that we've never seen before. Something in the lines of What Dreams May Come and A Christmas Carol. The pacing is good, I never feel bogged down by too many unnecessary details. All scenes have a purpose, and they build to some kind of conclusion.
The major problem I found is the lack of climax. You sorta have one here, but it's just David TELLING us that Cassie will commit suicide at 10pm. But I can't tell you how I would change it because that's like end of your short.
What I'm thinking is that your story should be about saving Cassie instead of focusing on Ryan's backstory. I think that would give the audience more anticipation and suspense.
Formatting wise, you could've introduced the MAN as DAVID right away. No camera angles please. Some minor typos.
A rewrite would benefit you. Good job.
Memwipe - Sci-Fi, Action, Thriller (114 pages) - In a world where memories can be erased by request, a Memory Erasing Specialist desperately searches for the culprit when his wife becomes a target for erasure -- with his former colleagues hot on his trail.