Is $A$ regular if $A^{2}$ is regular?
Consider Lagrange's four square theorem. It states that if $B = \{1^{n^2}| n \geq 0\}$ then $B^4 = \{1^n | n \geq 0\}$. If $B^2$ is regular, take $A = B$ else take $A = B^2$. Either way, this proves the existence of irregular $A$ such that $A^2$ is regular.