We show that the virtual cohomological dimension of a Coxeter group is essentially the regularity of the Stanley--Reisner ring of its nerve. Using this connection between geometric group theory and commutative algebra, as well as techniques from the theory of hyperbolic Coxeter groups, we study the behavior of the Castelnuovo--Mumford regularity of square-free quadratic monomial ideals. We construct examples of such ideals which exhibit arbitrarily high regularity after linear syzygies for arbitrarily many steps. We give a doubly logarithmic bound on the regularity as a function of the number of variables if these ideals are Cohen--Macaulay.