A child’s social world is complex and rich, but has traditionally been assessed with conventional experiments where children are presented with repeated stimuli on a screen. These assessments are impoverished relative to the dynamics of social interactions in real life, and can be challenging to implement with preschoolers, who struggle to comply with strict lab rules. The current work meets the need to develop new platforms to assess preschoolers’ social development, by presenting a unique virtual-reality set-up combined with wearable functional near-infrared spectroscopy (fNIRS). As a proof-of-principle, we validated this platform by measuring brain activity during self-guided social interaction in 3-to-5-year-olds, which is under-investigated, yet crucial to understand the basis of social interactions in preschoolers. 37 preschoolers chose an interaction partner from one of 4 human-like avatars of different gender and age. We recorded spontaneous brain fluctuations from the frontal and temporoparietal regions (notably engaged in social-categorization and preference) while children played a bubble-popping game with a preferred and an assigned avatar. 60% of the participants chose to play with the same-gender and same-age avatar. However, this result was driven by females (>80% vs. 50% in males). Different fronto-temporoparietal connectivity patterns when playing with the two avatars were observed, especially in females. We showed the feasibility of using a novel set-up to naturalistically assess social preference in preschoolers, which was assessed at the behavioural and functional connectivity level. This work provides a first proof-of-principle for using cutting-edge technologies and naturalistic experiments to study social development, opening new avenues of research.