This paper looks into whether there are any differences in demonstration of attentiveness between different generations and different cultures. By attentiveness I mean a demonstrator’s preemptive response to a beneficiary’s verbal/non-verbal cues or situations surrounding a beneficiary and a demonstrator, which takes the form of offering. When and how often one would demonstrate attentiveness may vary according to such factors as generation and culture. Three groups of people from different generations and different cultural backgrounds (Japanese and Americans) served as the participants (280 people for the questionnaire data and 18 people for the interview data). It was investigated whether there were any differences among the participants in demonstration of attentiveness, in the reasons for demonstration of attentiveness, and in rating degree of imposition to demonstrate attentiveness. It was also examined whether there was any relationship between degree of imposition to demonstrate attentiveness and demonstration of attentiveness; and in which relationship (the relationship between a demonstrator and a beneficiary of attentiveness varied from very familiar to not very familiar at all) attentiveness was demonstrated. The data were collected using a questionnaire with six situations, based on field notes; and the interviews were conducted using the same six situations. The results show that in most situations there were no major differences among the participants in the choice of demonstration of attentiveness and the reasons for it. The participants chose to demonstrate attentiveness in four situations in the questionnaire, because they wanted to be of help to the other party. There was a relationship between degree of imposition to demonstrate attentiveness and demonstration of attentiveness in four situations. Overall, the interview data confirmed the questionnaire data.