This chapter focuses on the involvement of unpaid voluntary work in a project in charge of assisting and supporting refugees in an Italian town. In particular, it investigates the ambiguous nature and the risks related to this form of help by analysing the motivations that led some retired people to teach Italian classes to refugees as well as the meanings that these people gave to their actions. Drawing on ethnographic fieldwork and in-depth interviews among voluntary workers and refugees, the chapter intends to stress three main issues. First, it calls into question the framing of the help offered by voluntary workers in terms of unselfish gift. Indeed, their involvement is better located within a continuum between self-interest (gratitude, self-esteem, intercultural exchange) and altruism. Second, it describes the relationship between voluntary workers and beneficiaries as an asymmetrical power relation between the one who helps and the one being helped. Besides reproducing the victimization of refugees, this asymmetrical relationship solicits their gratitude for the help received. Third, it shows how voluntary workers tended to evaluate their help in emotional terms (listening, talking, encouraging), thus eliciting refugees to share their feeling by talking about their flight, family, and memories. This resulted both in hurting beneficiaries and in jeopardizing voluntary workers’ emotional stability.