You couldn't fill the outer glass as the inner one would get in the way of the filling! Just stand the 2 in hot water to expand the outer one, ice or cold water in the inner would help too.
I sometimes struggle to free the top of a new bottle of squash. I cut through the little plastic lugs to separate the cap then run it under a hot tap, after which it easily opens.
If we haven't used a glass decanter in a while (!) the stopper is often stuck. I just pour a little water around it and it come free. Not quite the same but its sparked a hint in me.
Put ice in the top glass and stand the two in a basin of hot (not boiling) water. The ice will contract the top glass and the hot water will expand the bottom one.
I would think the slightly bigger of the two. Based on my very rocky science knowledge, heat expands, so the slightly bigger glass should expand enough to free the smaller one. But that may not be accurate!
I've been told that one way of freeing a glass that's become lodged inside another is to fill one of them with hot water. But which one? (any better ideas?)