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The screenplay kept me reading till the end, where I kept wondering if the boyfriend survived. I particularly found the flashbacks to be smartly written, where one flows into the other, and the story to be well structured.
Couple of points:
You began the second scene ("INT. COFFEE HOUSE- LATER") just moments after the waitress left the table. That might not be necessary. You could simply have left the scene heading out and combined the first and second scene.
The first round of dialogue between the WAITRESS and the BOYFRIEND seems rather rushed. While with acting it might make sense why the BOYFRIEND was agitated quite quickly at the mention of the word "job", perhaps the scene might be further developed such that there is more conflict before he flares up.
WAITRESS I know... Look I gotta get ready for work, can you get the creamer?
Getting ready for work was perhaps unnecessary, as the waitress did not go anywhere else and stayed in the kitchen.
Before I go any further into the story, perhaps you might wish to consider giving your characters names and ages. I got confused at some points as to what happened as I jumbled up BEST FRIEND and BOYFRIEND.
BOYFRIEND I love you. WAITRESS (slyly smiles) Who doesn't?
IMO, these are great lines, and says something about the WAITRESS' personality.
Having the boyfriend outside the window to discover their tryst might not be believable, as BEST FRIEND and the WAITRESS should have been more careful.
'A sudden flash happens.' might be replaced with the transition "BRIGHT WHITE FLASH TO:". Perhaps other members who are more well versed in formatting could please assist to point out if this transition is accurate. Thanks!
I was out of this one on page 7 I'm afraid to say. Look, don't get me wrong the writing isn't all that bad. You have a large number of mistakes that can be fixed easily. The problem, for me lies in the story and the way you tell it. In my honest opinion short films have to get to the nitty-gritty quickly. None of this waiting around with pointless dialogue is needed. Why not get straight into things? You have a limited space to tell this story and you seem to be wasting it on details that aren't really too important. By page 7, I still had no idea what this was about, which is why I put it down.
As well as that, there are various writing issues that pulled me out of the read. For starters, there's no FADE IN, which is really just a generic thing that needs to be included in writing. As well as that, you don't name your characters, which is just frustrating (and admittedly one of my pet peeves). You have a main character who is literally just named "The MAN". Give me a name to associate this guy with. Make it a little more personal. Having a name is essential IMO. It allows us to relate names to certain character traits, as opposed to just thinking "That Man who was nervous at the start". Know What I mean??
Page 1: Your first sentence is WAY too long... Four lines with just one sentence reminds me of how Shakespeare would write. He also had the annoying habit of not including things like full-stops. The point is... It confuses the read. You've tried to cram too much information into one sentence which really ruins the message.
Page 1: "... looking as if he committed a crime." - Try not to include details that you can show. For example, why tell us that he's nervous, if you've already shown us through his behaviour? It's just redundant.
"Page 1: "INT. COFFEE HOUSE - LATER" - Don't waste our time with the same slug repeated. Just have a simple "LATER" and get it over and done with.
Page 2: "We read in SUBTITLE..." - Avoid having "we" in any of your screenwriting. It makes it incredibly redundant. You could just write this...
"SUPER: "A few hours ago"
Page 2: "... pulls out a coffee can and begins to make the coffee to start the morning" - Here we have detail that has already been implied. Does it really matter WHY she is making the cup of coffee?? No. She's making the cup of coffee. That's the important part.
Page 2: The Boyfriend's reaction is way too sudden. He goes from a happy man to a screaming fit and then back to happy. What? It's hard to get an idea of this guy's point of view if it's constantly changing. Keep it consistent. If he's going to get angry, we've got to see some sort of build-up. Most people don't just blow their top after one sentence. I'm not saying it's impossible... Just highly unlikely.
Page 5: BOYFRIEND You're damn right wow. (shakes his head in disgust)
- Use a the parenthetical function if you're going to have something in brackets. Additionally, don't have a parenthetical if it's at the end of the line. You could just write it in the action, instead.
It's not bad. It just doesn't get into the story fast enough, making for a rather dull read. It feels more like a feature length than a short, which isn't the vibe you want people to get.
Agree with the majority of what others have said, but to add bring something slightly new for your consideration, don't confuse the audiance! Start right away telling us what's going on. Don't just drop us in the middle of things and hope on the off chance we'll be really interested to continue reading. I know I wasn't. I stopped after page 5.
The dialogue needs to move your story along, or gives us some insight into the story. But I know judging by the first few pages, it's just mindless chatter that's unnecessary in my opinion.
Some of your action lines are describing the same thing again and again. Be straightforward with a character's image, emotion, locations, time, etc, etc.
I was also unable to understand the characters through your dialogue. They seemed to almost contradict their own feelings, or maybe, their feelings in general seemed bipolar (?)