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I actually really liked this. I didn't see either twist coming and I thought they were both pretty funny. I'm sure every man feels this way sometimes, and you did a good job of engaging the audience on that level. I liked the dialogue, too. It was a little long in some parts, but that's not too big of a problem. But I think you have a knack of writing comedic dialogue.
One thing I will say, the formatting seemed a bit... off? I'm not sure but it just didn't look right. Did you do the entire script in bold? I don't know. Perhaps brush up on the formatting or you could use one of the free script writing programs out there (I think there's a couple). There were a couple of minor spelling mistakes like 'no' instead of 'know' near the end of page 2. Maybe consider reading through and double checking.
With some minor tweaks, most notably the formatting, this'll be a pretty good script. Good job.
So I guess I'll start with the technical stuff first. No time for your opening slug. Usually scripts have a title page and then a "FADE IN" to start. I'm not a stickler with things like that but thought I'd bring it up in any case.
Your opening action block doesn't feel right to me. Six lines and it describes very little IMO. You chose to describe what Ricky is wearing but neglected the setting or his features. Clothes can say a lot about a person but I feel like there should be more. Simone doesn't get any description either.
Some grammar issues. "how come you didn't come out the other night." Should be a question. "no" should be "know". Just a few. A reread should clear it up.
Through through to page 3 and all we've got really is a couple talking heads. Shorts need to be all killer and no thriller. Action should be driving this thing with dialogue playing the support role. Any reactions from other customers or even the cashier whom I'm guessing would have some kind of baffled look on his or her face.
So I'm out on page 4. Sorry but too much talking about events that I wished you would have portrayed. I'm a believer in a good flashback scene and I think it could have used it here. Simone repetitively shouting Ricky's name from the street as neighbors yell for her to shut the hell up or something would have spiced this thing up. The way it is, it's more along the lines of a story about a story. Perhaps there's something more down the road and if so, I highly suggest trimming some fat off this thing so we can get there sooner.
I enjoyed your story for the most part. Dialogue flowed nicely, despite some grammatical issues. I tend to leave some typos and misspelled words in my stories too. It happens.
That first description block was a bit of an eye saw. Try to to keep it to three or four lines. Five if absolutely necessary. (but try and avoid five)
I got a chuckle on how she kept asking for that hot chocolate and he kept ignoring her and ordering more stuff for himself.
I noticed Simone was driven by the fact that she was being ignored by Ricky. So when we realize it was day dream and she's been talking the entire time. I laughed because she was being ignored once more.
Not sure I agree with John's suggestion of a flashback scene. Giving the ending, it wouldn't have worked. Maybe he shouldn't have jumped out on page four..lol
I'm big on dialogue myself. Now I don't feel it should be all dialogue, I cant agree with the fact that dialogue cant drive a story. Especially if it's a short. Just my two cents.
But for the most part I felt like you could have added something more. Maybe the fact it was just them two going back and forth. Maybe have them hold up the line, and have another customer try to get passed them. Simone could have flipped out on the customer. I don't know, something...
All in all, enjoyed the dialogue, it was a fast read. It was good effort