what about flash MP3 players?
I have an ipod 30gig but found it annoyingly bulky (I know its not much but still I like tiny flash devices especially when skating/jogging/biking).
I am always near a laptop or something I can change the music quickly to anyways. 1gig is more then enough music to get me through a day or 2 if not longer.
I bought a sandisk 1gig MP3 player as a supplement (had to be OS X and win XP compatible, work with Itunes and not proprietary ala sony, and tiny, USB2, and preferably cheap)
http://www.newegg.com/Product/Product.asp?Item=N82E16855125004
It's $120 at the egg (I paid $150ish at a local best buy near my office)
BTW the provided ear buds suck IMO. I use these Sony's which are one of the best for the price range.
http://www.newegg.com/Product/Product.asp?Item=N82E16826159209
Inner ear though, some people do not like that.
While it's not the best MP3 ever, I am really happy with it for my basic needs. The menu is really klunky compared to my ipod but still for what it is, it works well. The basic controls are good IMO for such a tiny package. Actually I hated the menu orientation at first but found it can be flipped which made me alot happier. Also, although it cant read itunes playlists, I can drag and drop songs from both windows and mac itunes. I just make playlists in itunes and drag them all at once into the MP3 player. Works great. Also accepts normal files too (system mounts like a removable HD)
Again, not saying it's the best, just saying keep your options open to flash devices too. Some major things to think about:
Song selection, qty - You GF randomly likes a huge selection at her fingertips. It's better if she is someone who listens to a album or playlist through. If she is one of those constantly reading the library to pick song by song then large MP3 player all the way.
Mac/PC compatible - if that is a concern at all. Alot of the creative stuff is not mac compatible which really pissed me off.
Uses - if she wants to jog or something with it, flash technology is better. Lighter and no skip.
Power - If she isn't very good about charging stuff or prone to take this on long outtings (6+ hours) you may want something that takes regular batteries/rechargables instead of a fixed rechargable battery. None of the fixed battery systems last that long before they recharging, especially after 9-12 month.
Anyways I know time is ticking but remember who and why and what. Also on a personal note, I hope you are taking her to dinner/night out or something too. Techno gifts arent so romantic for annaversary... Better saved for B-days, Xmas IMO. -just my personal opinion.