Synchronous speciation of hosts and herbivorous insects predicts a congruent topology of host and insect phylogenies and similar evolutionary ages of host and insect taxa. To test these predictions for the specialized herbivorous fly genus Urophora (Diptera: Tephritidae), we used three different approaches. (i) We generated a phylogenetic tree of 11 European Urophora species from allozyme data and constructed a phylogeny of their hosts from published sources. Superimposing the Urophora tree on the host-plant tree we found no evidence for general congruence. (ii) We correlated genetic distances (Nei distances) of the host plants vs. the genetic distances of associated Urophora species. Overall, the relationship was not positive. Nevertheless, for some pairs of Urophora species and host plants genetic distances were in the same order of magnitude. (iii) We collected allozyme data for pairs of thistle taxa and pairs of herbivores on thistles together with independent time estimates. With these data we calibrated a molecular clock. There was a non-linear relationship between phylogenetic age and genetic distance, rendering the dating of deep events in thistle–insect evolution difficult. Nevertheless the derived molecular clock showed that the split of insect taxa lagged behind the split of hosts. © 2005 The Linnean Society of London, Biological Journal of the Linnean Society, 2005, 84, 775–783.