I like this! I think you can make the metaphor a bit clearer for what chess means. Does it mean taking risks to get closer with someone? Is the moral of the story that you just have to play with the right person? Is the chess game between Jane and Charlie a challenge to Charlie's strategization of trying to get a girl? Or his decision to attempt playing at all? It seems at the end Charlie becomes opened up to the possibility that he doesn't have to be nervous and people will want to play with him. Is the story Charlie triumphing over his lack of self confidence, or his understanding that sometimes he'll lose a game no matter what?

Continuing this thought to the title - En Passant is a tricky move. One that seems illegal, but isn't, and catches people off guard at the first moves of their pawn and captures them. Is there any symbolic connection to these ideas with the en passant? Is Jane the one who employs en passant? Or Charlie?

I think making what the challenge is clearer will help viewers be able to align with the stuggle and story for Charlie and root for him - unless it is that we aren't supposed to be, and have a critical outlook on his approach to relationships. The way you set up the character in the beginning - he seems nervous, anxious to make friends, not self confident, and overwhelmed. This makes us want him to succeed, seeing him struggle. But he doesn't seem to want a relationship until Thompson brings it up. We haven't even met Jane yet when Charlie begins his journey to getting her. Perhaps by introducing her at the scene in the coffee shop, maybe ignoring Sadie to look at her, or somehow he goes to the coffee shop just to see Jane, will provide a similar extension of alignment.

By maybe also refining the chess analogy for example will clear up for the audience where they are in alignment to Charlie's story and wants.

But overall I think you've got a great start, and would love to see you experiment a little more with how you tell this story! You don't have to of course, I think my filmmaking style personally is a bit whacky, but this is your short film, have the courage to think of the ways you find personally will powerfully communicate these essences!

This is good development - how can we make it more vivid and personal? Think La La Land (I know, come on Haleigh you're really going to bring that movie into this) yes I am. Remember the montage of them throughout LA on the trolley and in the jazz club and running around with each other? Maybe you can experiment and do something similar to show them connecting more! You have limitless potiental here besides dialouge. But - if you do want to keep the weird jokes in, you can always do that within any experimental strucutes. All suggestions by the way!

From a story stand point - it seems too soon for Charlie to win at chess. He's taken a risk, but has he learned how to win the game, synoynmous with the girl, at this point? The parallel seems disjointed. Perhaps you can show Charlie taking risks at chess mid game for this scene.

Is this in like retrospect to the real charlie? Does the real charlie exisit here? If so, maybe explain this transition more and where exactly we end up. Is this imaginary charlie in his room? In a void?

Charlie closes the app, and stops before setting his phone on his nightstand, noticing the book of chess tactics placed there.

Lol I feel this.

Do we need to see him settle into bed, or will the change from him studying to him suddenly in bed scrolling have more of an impact?

Use CUT TO: indentation

by the lamp light?

I love love LOVE this analogy. It's very upfront though, so it depends on if you want it that way. Perhaps if you wanted to be more subtle, and lead the audience into this connection for Charlie, you could have Thompson mainly argue on one front: Charlie needs to learn how to take risks at chess, here's the book to learn how, and btw maybe call that girl while ur at it OR Charlie needs to ask this girl out, here's a book on risks, and maybe you'll get better at chess too.

Letting the audience make the connection with the main character may keep them more engaged, rather than have Thompson tell us the whole time.

Delete.

Eeeeek I love this!

board, calculating his next move.

You can capitalize things like this if you want to increase the importance of an action :)

Delete?

Himself?

Where did he go?? Perhaps you can delete, or clarify by saying, "Charlie looks up from his book."

Ok I see you James! Nice use.

Lol love this.

Confusing, if we are seeing Charlie from their perspective, what is this new perspective?

"And then turn back to" before is evil to me >:)

Ok - here is where I'm curious about what Charlie is doing in the mirror. Does he take them off and scorn at himself? Does he take them off and fall in love with himself? Basically why does he make this decision?

Also - I always try and find ways to communicate things without dialogue. Perhaps you could focus in on a pair of contacts on the counter, have him contemplate, and bam next shot Charlie is walking around with contacts in at the coffee shop.

I am confuzzled. Wasn't he already wearing the square frames? I don't know what sqaures means ??

Do we need to clarify another pause here? Or can he just start circling. Also - switch back to implies we have seen him do this before. Perhaps say "He circles the room as if he has been here for a long time."

"and then removes the glasses and puts on a square framed specs instead"? Going back to a "before" confuses the clarity of action a teeny bit here

Woah we have Charlie doing two different things at once in the mirror here! Is he sizing himself up or hunching over?

Ok - I will try not to be picky, but this sentence is very complicated for a screenplay. Think the essentials, what would I want a snarky producer to absolutely know? Messy bed, dark apartment, a figure standing in his bright bathroom. Experiment with how concise yet still clearly you can communicate these elements!

This is information mainly provided by the scene heading, so you can "early morning," instead of "morning," in that scene heading and delete it in the action to make this clearer!