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Wow, this was great though I don't think your title flatters your writing genious. History sounds bland and plain, and your story frankly isn't. I haven't really got any suggestions but I must say the first thing that stuck out was that little road block. I'm not saying that you have to change it, but it would be a good idea. Lots of good books go to waste because of rather slow titles. [And don't worry, I'm not being an ogre when I say that because, I, to know how it feels, titles suck!]
Another thing I found rather troubling is the amount of characters you brought out in the first chapter. Mainly, in a first chapter, you are just introducing the MC, one - four characters, the setting, a slight guideline as to what the reader is to expect (otherwise known as a drawer) and maybe a slight problem that isn't connected to the plot (boyfriend leaving, best friend hating you, etc.). Otherwise you cannot go overboard because you lose the reader with the large amount of characters and other info dumps that are not neccessary. This is another problem I suffer from so don't worry.
In one story I wrote, I ended up adding ten maybe even more characters the you're supposed to and immediatly whips started flashing because everyone who read it told to me to not place so much people in. The reason is because it is hard to learn about them as a person, and see some kind of root that could lead to character development or even personalities and trust me that is a major factor in successful writing. All the Bestsellers are stories with good character development and if you don't hit the nail hard with the hammer in the first chapter, its hard to rope the reader in during the rest. No one wants to read a novel with characters that have next to nothing personality or no major development.
Now, I'm just going to recollect the main points of that because I tend to blabber: lessen the amount of characters. Just a tad, keep Brad, keep some of the friends but don't have them all coming in at once because I can hardly remember their names. And...and place some more personality into them. They don't really shine like they should.
Another factor that stood out, and which trips many writers, is show not tell. You need to do more of this because all I can see is tell in chapter one though a lot of show in the prologue. Show not tell simply means that you explain things such as settings, events that are occuring and characters, romancising really, whilst tell is dumping information in front of someone like a slab of cold meat. What I suggest you doing is layering. This helps me to romance my writing up and it can also help you.
Layering is where you go through and remove or add things that makes the chapter more classical and smooth. You definitely have to remove the amount of characters and you have to explain such things as appearance of the school, of characters and some personalty (spice it up). When you explained Olivia, I got a very different picture.
See here as you say she is extrovert, well I actually found her quiet. I actually thought she was little more refined in herself then any of the group. Day dreaming as you pointed out fits her well but I wouldn't consider her 'out-going'. If you want to stick with this you have to place it in the dialogue and her actions because I'm getting a very different vibe. Add a joke or something, that's what I do.
All in all, this was a great read and I cannot wait to read more. There weren't to many grammatical errors, not something you couldn't fix with a little layering. I hope that my advice came to some help, I'd like to elaborate a little more but Mum is getting angry about me being on the computer to late. It's only nine pm, I don't see what's so bad about it. Nonetheless, I must be going, good luck in your future novels and chapters of this one.
Apple.