Polyploidization, the process leading to more than two sets of chromosomes, is widely recognized as a major speciation mechanism that might hold the key to Darwin's 'abominable mystery', as he referred to the sudden rise of angiosperms to ecological dominance. On their way to become polyploid most plants take the route through the production of unreduced gametes that might eventually lead to viable triploid intermediates able to backcross or self-fertilize to give rise to stable polyploid plants. Polyploids are almost instantly reproductively isolated from their non-polyploid ancestors; as hybridizations of species that differ in ploidy mostly lead to non-viable progeny. This immediate reproductive barrier referred to as 'triploid block' is established in the endosperm, pointing towards an important but greatly underestimated role of the endosperm in preventing interploidy hybridizations. Parent-of-origin specific gene expression occurs predominantly in the endosperm and might cause the dosage-sensitivity of the endosperm. This article illustrates, based on the recent molecular and genetic findings mainly gained in the model species Arabidopsis thaliana, the 'journey' of unreduced gametes to triploid intermediates to polyploid plants and will also discuss the implications for interploidy and interspecies hybridizations.