okok so there was this visual novel i used to play a few years ago and I FORGOT THE NAME OF IT UGH. i'll try to describe everything i remember about it: 

a girl in high school 
study for tests 
buy clothes 
a blue/green creature thing that talked about internet or something 
a "crazy" guy named blake(?)  
dates 
build up skills like makeup, cooking, grades (idk) 
you could go to the mall, a pizzeria, a pool, a beach, etc 

i think the game started with an 'H' but i'm not entirely sure. i just had a lot of fun playing this vn and i'd looove to play it again(: 

Magical Diary?

Here is the link, but the more I think about it, it's probably not what you are looking for:

http://store.steampowered.com/app/211340/Magical_Diary_Horse_Hall/