Unable to delete songs from iTunes on my iPod shuffle 2nd gen

When I try to delete songs on itunes to delete on my playlist for my ipod shuffle 2nd generation, the song is not deleting, it just remains there even when I click delete, how can i remove songs that I no longer want?

(NVMMM I figured out how, just click on the song then click on the delete button on your laptop)

(keeping this up in case anyone needs it :)

[Re-Titled by Moderator]