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The present research aims at comparing younger (21,5 yrs) and older (75,3 yrs) adult’s comprehension of utterances containing a homophone following a context sentence either neutral or biasing towards one sense of the homophone. Participants were asked to select the drawing that best fits the target ambiguous sentence. The meanings of the homophones differed or not in frequency and varied or not according to the familiarity judgments expressed in the younger and older generation. Results show a facilitating contextual effect on the semantic decision that increased with age. An influence of familiarity was observed at both ages with a larger selection of the dominant sense for the belonged generation. No frequency effect was noticed with an equal selection of the more and less frequent meanings.