Songs won't scrobble from ipod!

It's been like this months if not most of the time I've been on this site! It's be auto scrobbling at first but I discovered you have to press the scrobble button and sometimes my computer would crash or I wouldn't notice it so I would just shut down or whatever. Did I lose those? I remember I went on a school field trip for like 3-4 days and the bus rides were super long and I want to know what I listened to on that trip since a lot was going on in my head but it would be nice to know a solution. I've also gotten another ipod since then, I still have that one but I don't use that (itouch) cause I have the 160 classic which I like better. But I think only about 30 or so songs have ever scrobbled from my new classic. WHY? Itunes scrobbling seems to be the only one that works for me! I have tried scrobbling my own but it has lots of errors and won't do it, it did 15 songs litterally and they were all from different days... like 5 songs from like a week ago and 2 from yesterday and other randoms...