How do I stop my Converse from hurting?

Give them a wash! The fabric on your chucks may be a little stiff and until you really wear them in, it may take some blisters. So speed up the process by throwing them in the wash to get the fabric softened up a bit. PS My Converse have now become SO comfortable that I wore through a pair and had to replace them.

Why are Converse uncomfortable?

The gist of the corporate-speak: Converse has realized that most people who wear them find them kind of uncomfortable. As Bloomberg put it, this oh-so high-tech innovation comes after "a billion sore feet." Converse have been cool, but their thin flat soles have long made them difficult to wear.