This paper investigates the simplification problem in Gaussian Half-Duplex (HD) diamond networks. The goal is to answer the following question: what is the minimum (worst-case) fraction of the total HD capacity that one can always achieve by smartly selecting a subset of k relays, out of the N possible ones? We make progress on this problem for k = 1 and k = 2 and show that for N = k + 1, k ⋯ |1, 2} at least k/k+1 of the total HD capacity is always approximately (i.e., up to a constant gap) achieved. Interestingly, and differently from the Full-Duplex (FD) case, the ratio in HD depends on N, and decreases as N increases. For all values of N and k for which we derive worst case fractions, we also show these to be approximately tight. This is accomplished by presenting N-relay Gaussian HD diamond networks for which the best k-relay subnetwork has an approximate HD capacity equal to the worst-case fraction of the total approximate HD capacity. Moreover, we provide additional comparisons between the performance of this simplification problem for HD and FD networks, which highlight their different natures.