iPod touch Confusion with checkboxes

[mx16m]

I have a first gen. iPod touch with the most up to date iTunes on my MacBook Pro. I am having some trouble figuring out the check boxes. I have some songs unchecked in iTunes so they won't sync to my iPod, but when I put the songs in a playlist iTunes skip past them. Is there anyway I could have unchecked songs in my iTunes library that won't sync to my iPod, but will still play when on shuffle on my MBP? I know this is kinda confusing, sorry. Thanks in advance!

 

[pacers721]

i have this same problem. i far as i know, there isn't a way. It seems there is a way to do the opposite (have on ipod and skip when shuffling of mb)...