Time Machine and Windows are definitely speaking on the same topic / person(s). But contrary to Windows, this one sounds a bit hopeful/optimistic.
I can really relate to the lines -
I wish that I could take all of those feelings away
Throw them in a canyon,
Bury them in the sand
Wanting to console, being helpful but feeling helpless at the same time.
On a another note, I would love if Jason could give some comments on this collection of songs like he did with Paper Cuts