AZlawyer
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I think it was written '08 because of a few things:
1. The '03 is only on the LEFT HAND page. That one might have been written in '03. It does kind of match with the RIGHT HAND page, but as you'll see, I don't think they go together.
2. The tone. I don't know about you, but the RIGHT HAND page doesn't sound like something I would have written in my junior year of high school. Maybe when I graduated and was going off to college - but Casey never graduated, never went off to college. What in the world would have her being so introspective in high school when she didn't graduate and wasn't heading off to college at all? There was nothing big going on around that time of her life, that we know of, that would cause the kind of writing on the RIGHT HAND page. But Killing Caylee, and getting a new, Caylee free life - that would cause to her write what is on the RIGHT HAND page.
3. Tone again - The LEFT HAND page is definitely high school, or at least something a girl would write upon getting a new diary. Notice how many pages are missing between the LEFT HAND page and the RIGHT HAND page. I'm thinking she had this diary since '03, kept a pink pen with it, and only wrote in it sparingly. Five years is a long time to have one diary unless you don't write much in it. Casey doesn't strike me as the kind of girl who writes novel length diaries. I'm not totally sure about this one, but I'm giving the fact that '03 is in the corner the benefit of the doubt.
4. It looks to me like she got rid of the middle of the diary in case her mother ever found it. I'm sure she wrote about her sexcapades and stuff like that. Can't have mom stumbling on that and finding out her innocent little girl isn't innocent at all. The first and last page were vague enough that she thought it could be applied to anything, so she left them there - plus, if she did write that RIGHT HAND page in '08, she definitely was not going to get rid of it.
5. The timing. The RIGHT HAND page date is June 21 - that would be what, five or six days after Caylee's death, around the time she dumped Caylee for good, right? That would be the perfect time for her to be thinking she got away with what she did and contemplating, without the distraction of Caylee's body, for the first time about life without Caylee. It fits perfectly in the timeline of what happened to Caylee. That can't be a coincidence.
6. Timing again - why on earth would she write an entry like that in the summer of '03? I can see maybe writing something like that because of stuff happening during the school year, but it seems odd and out of place to write something like that when school is out for the summer. And it doesn't make sense that she'd meet a new group of people just weeks after school let out. It's not like she went to camp or anything like that that we know of.
To me, the RIGHT HAND page screams '08, after Caylee was dead and dumped. The LEFT HAND page could be from '03, or it could be from '08 - that one I'm not so sure about. But I'm certain about the RIGHT HAND page.
These are all the reasons I keep going back & forth on this one. Also, one reason to rip out all the diary pages before that one might be to say, "All the rest of this crap doesn't matter any more. I'm starting my new life."
For those of you who think she would never have written this down because of the risk that it would become evidence against her, remember that this is the same girl who posted the "everyone lies, everyone dies" poem on her MySpace page in early July for the entire world to see and also kept a carefully cut-out sticker backing in her Caylee keepsake box, possibly to remind her of the sticker she left on her dead daughter's duct-taped face.