This study was conducted to compare the factors that student dropouts report as contributing to their dropping out of school with those factors that "at-risk" students report as influencing their attitudes toward school. These two sets of factors, assessed in two separate studies, include in-school and out-of-school experiences, socioeconomic factors, and participant attitudes toward schooling in general. The two studies obtained in-depth interview data from 65 white female school dropouts participating in the Kentucky Department of Education single parent/displaced homemaker programs and 68 white female disadvantaged high school students considered "at-risk." Findings revealed that respondents from both studies consistently reported home-life experiences which were highly incompatible with school demands (lack of discipline, little parental interest in school/education, many home responsibilities, financial problems, abuse). Respondents from both studies reported problems with peer pressure, drug use, and absenteeism. Other findings concern the relationship between teenage pregnancy/parenthood/marriage and dropping out. (TE)