This study examined the relationship between the damage of bullying in junior high school and school adaptation after entering high school. Three surveys of 281 high school students were conducted at various points in time. The first survey was conducted immediately before the respondents started high school to measure the extent of bullying respondents had experienced in junior high school. The second survey was conducted in June, shortly after the respondents started high school, to measure their depressive tendencies and future prospects. The final survey was conducted in November to measure the extent to which respondents had adjusted to high school. An analysis of the survey results suggested that the “prosocial effort orientation” factor and the “positive and active future image” factor that compose a positive future outlook may be related to the process by which being a target of bullying reduces an individual’s ability to adjust to school.