Abstract In the present article we introduce two new combinatorial interpretations of the r-Whitney numbers of the second kind obtained from the combinatorics of the differential operators associated to the grammar G := {y → yx m , x → x}. By specializing m = 1 we obtain also a new combinatorial interpretation of the r-Stirling numbers of the second kind. Again, by specializing to the case r = 0 we introduce a new generalization of the Stirling number of the second kind and through them a binomial type family of polynomials that generalizes Touchard’s polynomials. Moreover, we recover several known identities involving the r-Dowling polynomials and the r-Whitney numbers using the combinatorial differential calculus. We construct a family of posets that generalize the classical Dowling lattices. The r-Withney numbers of the first kind are obtained as the sum of the Möbius function over elements of a given rank. Finally, we prove that the r-Dowling polynomials are a Sheffer family relative to the generalized Touchard binomial family, study their umbral inverses, and introduce [m]-Stirling numbers of the first kind. From the relation between umbral calculus and the Riordan matrices we give several new combinatorial identities