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Participation in romantic relationships during adolescence and young adulthood provides opportunities to explore one’s sexuality, yet may also cause distress once these relationships dissolve. Although researchers have asserted that participation in same-sex relationships may be beneficial for young gay and bisexual men’s (YGBM) psychosocial well-being, less is known about YGBM appraisals of breakups after participating in same-sex relationships. We examined the association between self-reported psychological well-being (e.g., symptoms of depression and anxiety; self-esteem, sense of personal competency) and YGBM’s negative and positive appraisals of breakups within a sample of single YGBM (N=1,040; ages 18–24) who reported prior serious same-sex relationships. Negative appraisals were associated with lower psychological well-being. Positive appraisals were associated with greater anxiety symptoms, self-esteem and sense of personal competency. Our findings highlight the need to acknowledge how YGBM’s differential responses to breakups may be associated with their psychological well-being.