A survey of 1,860 15-year-olds from across the United States found that mentees' perceived positive regard from caring adults was associated with a range of personal, school, and civic outcomes. A structural equation modeling analysis found that for youth who have a mentor or other caring adults that they feel "gets them," this perceived positive regard was positively related to youth's sense of purpose and effort in school, which are related to higher grades and civic engagement. A person-centered approach found associations between feeling 'gotten' by a caring adult and higher academic and civic engagement. Results also demonstrate potential negative effects for youth who perceived low positive regard from an adult. Implications for research and practice are discussed.