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Message to Readers
I like the premise of this. The storyline is very good, and although jumbled at times, I think it's a really good idea that should be expanded on.
I found a few things worth addressing. First of all, you use the same transitions a lot. Vary your language to make your writing more interesting. You don't have to have a transition after every sentence; the story should flow without them. Second, you break the fourth wall a lot. This is when you talk to the reader. Even in a diary entry, this is something an author should avoid at all costs. Third, when events should be dramatic, you kind of play them down. Like, this guy gets arrested for beating someone almost to death, and everyone's just like "meh". Don't be afraid to dramatize! That's what gets a reader hooked! Also, you change tenses often. It's a diary entry, so it should all be past tense. Don't stray from that. Lastly, the ending is very confusing. Are you going to add another entry, because if this guy falls out a window, I want to know what happens. You just end it on "oh he might have died, no big deal". Yes, it is a big deal! Expand on that idea! You have the ideas, but they seem a little boring in practice.
So sorry if this review seems harsh, I just want your writing to be the best it can be! Please don't hesitate to ask me to explain anything, and I think you have an awesome idea here that can be taken really far.