Objective. This research demonstrates that interoceptive attentiveness (IA) can modulate cortical oscillations related to the emotional and cognitive representations of observing pain in others. Methods. Twenty participants were required to observe painful/nonpainful stimuli in an individual versus the interactive condition during the recording of the electroencephalogram. The sample was divided into experimental (EXP) and control (CTR) groups, and the EXP group was explicitly required to direct the attention on its interoceptive correlates while observing the stimuli. Results. Mixed repeated measures, analyses of variance, were applied to each EEG frequency band. Significant findings were obtained mainly for theta and beta bands for the two groups. A hemispheric lateralisation effect was found, with right lateralisation of the theta band for the EXP group when observing painful stimuli and enhanced left activation of theta and beta bands for the CTR group when observing nonpainful stimuli. For both groups, frontal cortical regions were significantly sensitive to social scenarios, while posterior parietal activation was found for stimuli depicting the individual condition. Conclusions. The results suggest that IA might enhance the emotional representation of painful stimuli, highlighting their negative and unpleasant features in the EXP group, while the attention of the CTR group was mainly drawn to nonpainful stimuli in social and individual conditions, with a positive valence. The role of frontal regions in the processing of social stimuli through social cognition, inducing emotional mirroring and requiring deeper analysis of the social context, was underlined. We propose that IA could be trained for promoting emotion regulation and empathic response.