Relativity of Time for Two Observers

[FactChecker]

I think it's more like saying I'm 100 miles from Pittsburgh and youre 1000 miles from Pittsburgh and that's a contradiction because it means Pittsburgh is in two places at once.

Or is it like I took a 100 mile round trip beginning and ending at Pittsburgh and you took a 1000 mile round trip beginning and ending at Pittsburgh and that's a contradiction because it means Pittsburgh is in two places at once.