Seed size is a fundamental life-history trait for plants. A seed number/size trade-off is assumed because the resources invested in reproduction are limited; however, such a trade-off is not always observed. This could be a consequence of the method used for testing it, where the null hypothesis is dictated by common statistical practice, rather than being based on any underlying theory. Alternatively, there might be some population- and species-dependent variables that affect resource availability and, in turn, influence the presence and intensity of this trade-off. Using data on 42 herbs from two communities (lowland and alpine) from Southern Norway, we tested the validity of the classical linear model vs. two previously proposed models, based on resource competition, when assessing the existence of this trade-off at different levels. We also evaluated whether some species- (fruit aggregation, ovules/flower) and population-dependent (pollen limitation) variables could affect this trade-off. Classical linear modelling outperformed the other proposed functional models. Significant seed number/size relationships were negative in single-fruited species, whereas they were positive in species with infructescences of one-seeded fruits. Concordantly, fruit organization was the most influencing variable for the intra-specific trade-off in the lowland community. In the alpine community, species suffering higher pollen limitation showed more strongly negative slopes between seed size and seed number at the fruit/infructescence level. Across species, seed size and number were negatively related, although the relationship was significant in only one of the communities. No evidence of trade-off was found at the plant level. Linear models provide a flexible framework that allows coping with the variability in the seed number/size relationship. The emergence of the intra-specific relationship between seed number and size depends on species- and population-dependent variables, related to resource allocation and the pollination environment.