Here are the possible solutions for nate's and chuck's girlfriend at different times of course clue
Answer
Clue
Relevancy
blair
Clue
Nate's and Chuck's girlfriend (at different times, of course)
sarah
Clue
Chuck's girlfriend on TV's "Chuck"
smokeweedeveryday
Clue
Suggestion uttered by Nate Dogg at the end of Dr. Dre's "The Next Episode" (The views and opinions expressed in this answer are not necessarily shared by The Cross Nerd Inc.)
ellie
Clue
Chuck's sister, on 'Chuck'
ifa
Clue
"... woodchuck chuck, ___ woodchuck could chuck wood?"