The aim of this paper is to investigate the potential of online group activities alongside one-to-one offline counselling in youth work targeted toward young adults not in employment or education. The study examines the feasibility of moderated anonymous online group (MAOG) discussions from a comprehensive standpoint, with reference to the perspectives of end-users, service providers and further research. The paper is based on a two-arm, quasi-experimental and mixed methods study. To this end, the data consists of group interviews with young adults and youth workers arranged at the beginning of the study, baseline and follow-up interviews, online discussion threads, as well as evaluations of the online group activities. The piloted intervention was most acceptable to young adults who suffered from loneliness and had difficulties in joining face-to-face groups. Most youth work professionals considered the pilot viable. Finally, several modifications are suggested prior to implementing an experimental setting to study the effectiveness of the intervention.