|The biggest problem by far is that this is clearly a plot with the complexity of a short film padded out to the length of a full movie. Every other issue in the script stems from that one problem. 95% of this, without exaggeration, could have been easily removed without any of the story being lost.
The plot is very poorly structured. The rule of starting the story as close to the climax as possible is grossly violated leading to an overly long, overly boring exposition with far too much information. There is no Inciting Incident, a scene where we see a major change in Stanley's life that jump-starts the rest of his journey, causing the rest of the story to read more like a series of days where things just happen than an actual plot. I believe the only strong element of the plot is the climax where Stanley shows up late to work, as it shows us how he is finally able to free himself from a toxic need that destroyed his old relationship and almost costed him his new one. After this, the resolution should have consisted of him asking out Rita and that marking the end of the film. However, instead of doing that, the film pads itself with additional unnecessary conflict and repeated information, which bogs down the story and makes the ending a bore to sit through
Far more exposition is used than actually needed. You frequently stop or delay the story to tell flashbacks that give information that could have been delivered much better in a single sentence. Information is also often thrown at the audience before they would have any desire for it. The most egregious example of this is the flashbacks in the beginning where you give us information about the characters before we've even met them.
Despite making sure the audience knew extremely minute details in each character's past, you neglected to tell what, in my opinion, was the most important detail: Why is Stan obsessed with always being on time? (even after we see it cause the death of his wife). Even if you didn't give us the most logical reason, this simple insight onto the main character's motivations would have given us a lot more reason to root for, or at least understand his actions (especially after he forced Rita to arrest the robber at his office).
Finally, the dialogue and interactions in between characters aren't natural or entertaining. Most exchanges can be described as one character delivering information to the audience, and then that exact bit information just being repeated 10-15 times. Characters also remain static from the beginning to the end of each scene making a lot of them feel pointless.
I feel like that at the end of the day, this is a really good story being choked by horrendous storytelling. I believe that if it were rewritten into a 10-20 minute film, it would pretty nice story, but as it stands now, it's extremely boring and a pain to read through.