Friendliness is essential for the development of stable interpersonal relationships. Video communication is growing rapidly in popularity for initiating and maintaining personal relationships, but it is unknown if video communication is as effective as face-to-face communication for promoting friendliness. This study compared the development of subjective friendliness between video and face-to-face communication sessions and investigated the associated neural correlates. Thirty healthy same-sex pairs were recruited and randomly assigned to face-to-face (Face) and video communication (Video) groups. Both groups performed three communication conditions face-to-face or via the Zoom platform in separate rooms: singing a song alone, singing a song with the other pair, and listening to the other pair sing a song. Activities of the bilateral dorsolateral prefrontal cortex (DLPFC) and medial prefrontal cortex (MPFC) were measured during the condition by functional near-infrared spectroscopy (fNIRS), and subjective friendliness was assessed before and after each condition using the Profile of Mood States 2nd Edition (POMS-F). After each condition, the change in POMS-F score (∆POMS-F) was compared between groups, and correlations were calculated with regional brain activity measures. Face group showed an increase in all conditions in ∆POMS-F, and Video group showed in average a decrease, which results in significant group difference in ∆POMS-F. The Face group showed a significant positive correlation between right DLPFC activity and increase in ∆POMS-F, whereas the Video group showed marginal significant negative correlation. Additionally, left DLPFC activity was significantly higher and MPFC activity was significantly lower in the Video group than in the Face group during all conditions. These findings suggest that subjective feelings of friendliness may be limited during video communication due to a requirement for greater cognitive effort.