Undercooled wetting films near a first‐order wetting transition exhibit an unusually long lifetime: the thermal nucleation barrier for formation of a critical hole in a film of thickness F diverges according to Γ ∼ exp (ℰc/kBT) where the excess free energy ℰc ∼ Fζ with ζ ≥ 2. Localized perturbations of the liquid‐vapor interface (‘dimples’) are shown to be a useful tool in reducing Γ in a controlled way: they act as heterogeneous nucleation centers for thermal critical nuclei. For 4He wetting films on weak‐binding alkali substrates (Cs, Rb) dimples can be generated either by vortices in a superfluid film or by surface electrons. The theory of the heterogeneous nucleation process initiated by the presence of surface dimples (‘dimple‐assisted dewetting’) is developed, accompanied by quantitative predictions for experiment.