The purpose of this study was to examine the effectiveness of our outreaching intervention among hikikomori individuals, based on the data collected from our outreaching practices targeted on hikikomori youths in Tokyo, Japan. Logistic regression analysis revealed that “family relations” motivated youths’ help seeking behavior, and youths in the duration of 1-5 years were more likely to accept the home visiting intervention. Furthermore, youths who started hikikomori during school years are more likely to recover social connection than those who started it during the transition to employment. Thus, it was indicated that their experiences of having support during school years would make it easier for them to accept intervention and create rapport with the workers, and which would induce better outcomes.