I have never previously managed to keep a diary. I always wanted to - especially when I was young, because the girls in books tend to keep diaries, and they were my best friends. I still, every couple of years, go a buy a nice journal and then sit starting at the blank pages for a bit before admitting defeat and using it for notepaper.
I think the problem is in starting it - if I could get a good solid first line then I'm sure I would become a veritable font of eloquent insights and poignant observations. But what are you supposed to call the diary - who are you writing to? Do you name them? What is there relationship to your life - do they know the people you do, or should you make introductions? The first lines are full of so many decisions, which set the tone for the whole rest of the project - and that is just too much pressure to put on 'Dear Diary.'
This diary was easy to keep. I was writing to my boy. As it turns out, I can't even imagine a better friend than him, and so 8 months later I do not have a book of old shopping lists, but a slightly late valentine's present and a urge to go journal shopping.