I'll hate myself for this....I just know it.
It appears like you have some real talent as a writer, but the problems I saw in the script stem from the specifics of Screen Writing.
You can be a good writer, but not a good screen writer and that is what it looks like in this particular script. It has the promise of a good solid style and the dialogue isn't bad in parts so you have some talent as a writer for sure. Now don't get mad (you asked for "brutal" honesty) so here it comes.......
I think you need to put more effort into writing a visual story as first priority and stop leaning so heavily on the unseen elements. This is something that every new screen writer has to overcome, and the good news is that most of them DO overcome it and move to the next level, but if someone doesn't step up and point it out to you, you may not see it. Here are 2 examples from the first couple paragraphs.....
"A young professional woman, JESSIE, is storming down the sidewalk toward the entrance of her apartment building after a horrible day at work."
The mood is set and the scene opens with some good strong visual elements, but you added some extras that should have been left out (for 2 reasons). The camera can not show "after a horrible day at work" so that was just there for the reader of the script. Don't jump all over me yet ok it's just an example. You could have left that part off and left a little suspense for a few paragraphs later. I know it is hard to write words that are 100% visual and sometimes we have to include a few non-visuals to help the reader understand things.....but I don't think that is what you were doing here. Take that same opening and make it a strong VISUAL. You can see all the elements except the bad day example:
You can see: a young professional woman
you can see her: Storming down the sidewalk
you can see: the entrance of an apartment building
but you can not see that she had a horrible day at work, so leave it off and the story (believe it or not) actually becomes much more engaging. It grabs you faster because you have no idea what is going on yet and that is a good thing many times. The next shot would then build on that:
"JESSIE comes in the door, dumps her purse and the mail onto the floor, and throws her coat in the other direction on the floor"
Much better this time because all the elements are indeed visual...you can SEE all these things and if we did NOT already know that she had a horrible day, the viewer/reader is now thinking "hey what's up with this gal?" and it draws them in.
Then you go back to the crutch again......
JESSIE slumps onto the couch, clearly annoyed with her day.
All we can SEE is the slumping on the couch we can not see "clearly annoyed" so leave it out......these things need to be discovered not "told to us". Then the dialog commits the worst infraction of screenwriting. This is the "writer" in you overpowering the "screenwriter" in you.
JESSIE
(sighs)
That had to be the worst day of my Life! I'm glad it's finally over
People NEVER do that. They do not have dialogue when sitting alone in a room. This is only there so the writer has a easy way to show the part he is having trouble with (namely the horrible day thing). Never ever have the character just blurt that stuff out....it just takes people out of the story right away. Instead have her just sit there. She can sigh (that is appropriate) but never have a character just say something because you as the writer can not think of a way to convey it visually. Wait til the room mate gets home and then have her say it, but then she is at least talking to another person........or have her slump down on the couch and sigh then glance over at her diary on the coffee table. She opens the diary and puts a big red X though the day and writes "today sucks" then closes the diary and drops it to the floor, or she gets a call and answers the phone saying "look I had a really bad day can I call you back later" or....or....or the list goes on
I am not trying to nit-pick just pointing out a few Very specific examples . I always find specific examples are easier to get a handle on versus when someone just gives me general feedback about overall feelings or impressions...... I find it more helpful when a critique includes these, because for me when someone tells me "It just didn't work for me" I have no idea what to do with that info....but if they say "Stop being a writer and start being a screen writer" that makes more sense usually. Spend some more time with the visuals....there is ALWAYS a way to write the story visually but it takes more time and effort and it is an aquired skill. Also by leaving OUT the crutches you allow the story to build naturally and it becomes more interesting.....if we didn't know right away that she had a bad day, we would wonder why she was acting so strange and would want to keep watching to find out.
I hope you take this in the manner it was intended, the last thing I want to do is turn anyone OFF from writing....you absolutely do have some talent and it shows very well in certain areas of the script, so keep going man.........just try to remember your script will be filmed not read......write visually and everything will start to flow easier for you because you will begin to see the story in your own head. Don't take the shortcuts of a writer.......use the minds eye of a script writer instead.
You could re-write this same script and turn it into a much better story and much less predictable...consider it a challenge. I know you said you are not crazy about the story, so that is exactly why you should re-write the thing and try to incorporate some of the visuals and the suspense.......it would be an excellent assignment. See if you can make THIS story into a better story. You may not dislike it so much the next time around. Heck, maybe we should all take this assignment on and try to re-write the story to make it more engaging.
Don't flame me......just trying to offer a few observations to help out a fellow screen writer. Besides it's just one persons oppinion so you can always ignore it completely........what the heck do I know anyways hahaha.
Take care
Frank