Calling All Writers!

I need help.

I am piecing together a new work to submit for publication. I have about 100 pages of material right now, I am just having trouble coming up with a cohesive way to tie everything together.

Here's what I envision:

An anthology of creative non-fiction pieces (mine) that are chronologically tied together. Has a diary-like feel, each entry separated by date. Not every piece is long. Some are one liners, some are three pages. In total, I'd like it to be about 150 pages.

My working title is "Weaving a Basketcase". I have a couple of subtitle options I am toying with. I don't even know if a subtitle is necessary.

Possible subtitles:

The Anatomy of a Break-Up
The Diary of a Hopeless Romantic
A Compilation of Notes to Myself
Blogging Myself Whole Again

Most of the pieces are posts from my blog from 2003 - Present and most of them have to do with my love life.

What I am struggling with is if this will even be readable. If you have read me before, please leave your comments.

Or, if you promise to be constructive, I will send you a copy of the working manuscript and you can tell me your thoughts. I am particularly having trouble with the transitions between posts/pieces. I don't know if people will have a hard time following the chronology, even with the date.

This is something I've wanted to compile for a while now; I just don't know if it's possible or how I would even begin to make it cohesive.

Any help you can give is much appreciated!

Thanks. :)