So you're getting bugged with people asking you what choons you like?

Just take a copy of your WinAmp playlist and send them that!

But how is the file laid out?

This is just a header to the file. I think the #EXT means it's not a filename
#EXTINF:423,Baz Luhrmann - (Everybody's Free) To Wear Sunscreen
E:\music\Baz Luhrmann - Sunscreen.mp3
Here's a file where the track has been indexed. WinAmp has extracted the name from the ID3 tag, and the '423' means that there are 423 seconds (or 7 minutes, 3 seconds) in the song
E:\music\Lemon Jelly - Lemon Jelly - Kneel before your god.mp3
This one hasn't been indexed. Just the plain filename.
Pink Floyd - Another Brick In The Wall Pt 2.mp3
This one isn't in the E:\music\ directory, but in the local directory #EXTINF:240,Wayriders - Hazy
E:\music\Wayriders - The Moose -9 - Wayriders Promo - Hazy.mp3
And the file just ends there. No tailers, that's it.

And your friend now knows what songs you have, don't have, if they're full versions, and other cool foo.