Laboratory studies have demonstrated beneficial effects of making comparisons on children’s analogical reasoning skills. We extend this finding to an observational dataset comprising 42 children. The prevalence of specific comparisons, which identify a feature of similarity or difference, in children’s spontaneous speech from 14–58 months is associated with higher scores in tests of verbal and non-verbal analogy in 6th grade. We test two pre-registered hypotheses about how parents influence children’s production of specific comparisons: 1) via modelling, where parents produce specific comparisons during the sessions prior to child onset of this behaviour; 2) via responsiveness, where parents respond to their children’s earliest specific comparisons in variably engaged ways. We do not find that parent modelling or responsiveness predicts children’s production of specific comparisons. However, one of our pre-registered control analyses suggests that parents’ global comparisons—comparisons that do not identify a specific feature of similarity or difference—may bootstrap children’s later production of specific comparisons, controlling for parent IQ. We present exploratory analyses following up on this finding and suggest avenues for future confirmatory research. The results illuminate a potential route by which parents’ behaviour may influence children’s early spontaneous comparisons and potentially their later analogical reasoning skills.