Did you used to make mix tapes for your friends, and particularly your more-than-just-friends? I know I did. Road Trip mix tapes. Romantic Weekend mix tapes. I Miss You mix tapes.
To burn a CD in iTunes you have to create a Playlist. Create your Playlist of Valentine's songs, but replace all the album art with pictures form your vast collection of shots of you and your loved one. (This is pretty much a drag-and-drop operation from your photo library (perhaps iPhoto) to iTunes.
When the object of your affection rips your CD gift, it will be added to iTunes as a Playlist and synched with the iPod next time around. When listening to the Playlist on the iPod, your loved one will see the pictures you added on their screen.
My suggestions for Valentine's Day songs?
Anita Baker - Caught Up in the Rapture or Sweet Love
Annie Lennox - Primitive
Bill Withers - Lovely Day
Bonnie Raitt - You
Brian McKnight - The Only One For Me
Dave Matthews Band - Crash Into Me
Elton John - Tiny Dancer
John Hiatt - Have a Little Faith In Me
Johnny Clegg and Savuka - Dela
Luka Bloom - Black is the Color
Midge Ure - Fallen Angel
Paul Westerberg - Born For Me
Pete Townshend - Let My Love Open the Door
Peter Gabriel - In Your Eyes
Rickie Lee Jones - It Must Be Love
Seal - Come See What Love Has Done
Shawn Colvin - This Must Be the Place (Naive Melody)
Tonic - Sugar
Hat tip: simplehuman