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Background: Interpersonal emotion regulation (iER) is the process of managing others’ emotions and is critical during early adolescence, when social awareness and peer dependence increase. Little is known about how sex and gender role orientation shape adolescents’ iER. This study examined whether early adolescents differ in their use of person-focused (acceptance) versus problem-focused (positive engagement) strategies and whether these differences depend on context and measurement method. Methods: Data were collected from 322 adolescents (141 girls, 181 boys; aged 10–14 years, M = 12.47, SD = 1.55). The cross-sectional online study used a multi-method design comprising open-ended visual vignettes, a standardised questionnaire, and a serious game task. Participants also completed a validated gender-role self-concept measure assessing femininity and masculinity. Analyses were conducted using Poisson and logistic regressions with sex, femininity, and masculinity as predictors. Results: Across tasks, adolescents preferred problem-focused over person-focused strategies. Girls and those higher in femininity reported or generated more acceptance-based strategies, whereas boys and those higher in masculinity favoured positive engagement. These effects were evident in reflective measures (vignettes and questionnaire) but not in the interactive game, where sex and gender differences were absent. Conclusions: Findings suggest that gendered socialisation processes shape how adolescents regulate others’ emotions, particularly when behaviour is consciously reported. However, in ecologically valid contexts, these differences diminish, indicating shared capacities for adaptive interpersonal regulation across genders.