I really enjoyed your writing and your sense of humor is very evident throughout this script. I also think you structured this story very well and you kept it going at a good pace. However, overall, I don't think the subject matter quite works for a screenplay. While this would be an exciting and funny story to tell at a party, it's a little too mundane for a movie, unless you add in some very profound and moving dialogue. In order to make it a little more interesting, I think you could try and add more conflict within each scene. Some scenes, such as Marie talking to her roomate, tend to drag on a little. I also think Marie's conversation with Boppa on the train could be heightened for more interest. As it stands, Marie's inability to comprehend why she's so entitled kind of seems like millennial bashing (even though she is not a millennial). I think this scene could use more nuance in the dialogue regarding what they don't know about each other's lives. One thing that could really benefit this story is giving Marie's character more of an arc. As the story stands, no one really changes and Marie doesn't learn anything except why she's entitled. I think there's more room for her to show how her trip with Boppa changes her. I also would work on the dialogue between Boppa and Nanna toward the end. This is an important scene, but it leans toward cliche. I think this could be a lot more moving to the reader with a few tweaks to the dialogue. A smaller thing to note-I would consider changing Mia's name. Mia and Marie are too similar and it can be a little confusing for the reader, especially before they get to know the characters.
Love the concept of this, and there are some very well written scenes and unexpected twists, such as his wife lying about being on bed rest. One thing that I think could be improved upon is William's dialogue. His aggressive language is a little over the top, and I think it could be better to show his "lost sense of self" through action rather than through his aggressive language. I largely think this because of his transformation throughout the script. His language makes him such an extreme that his character seems to go from a very harsh personality to an almost soft one too quickly - especially in scenes with the counselor. I also think there are a few lines that don't line up with how I picture him as a reader. Lines such as "They ain't coming" and the use of the word "brah" don't seem to match the more sophisticated middle age man I see him as, regardless of how troubled he is. Another thing I might reconsider is Oliver's character - he's a great character, but I would make him more of a comic relief based on the fact that he is seemingly unshaken by his idol not matching up with how he probably pictured him. If he's not an almost comically unshakable optimist, it's confusing as to why he wouldn't fear Billy or be more upset by him. One final thing of note is the breakdown William has about giving Celia medication. This may be insensitive to readers who have children that do have to take medication and may be grappling with it. Overall I really enjoyed reading this - and although I think you could soften his character arc a bit (a bit extreme as mentioned before) I really appreciated that I could see his change and the flashbacks that helped me understand his character as a whole. Well done!