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A total of 296 (101 male) participants from Great Britain and 235 (101 male) from Iran completed a questionnaire which measured respondents’ self-assessed character strengths based on the Values in Action Inventory of Strengths (VIA). It used a shortened version used in previous cross-cultural studies. It aimed to investigate culture and sex differences in, and the factor structure of, Character Strengths as well as the six Virtues which are the “higher order” classification of the strengths. Females gave higher ratings than males on Kindness, Loving, Gratitude and Enthusiasm, but lower ratings on Good Judgement and Bravery. Exploratory and confirmatory factor analysis provided some evidence for the six Virtues. In all, there were 8/24 significant effects for culture and 9/24 for sex, with 3 significant interactions. There was more nationality than gender main effects on the analysis of the Virtues, with British students providing significantly higher estimates on all, except Wisdom. British participants and the latter gave higher estimates on the Virtues Justice and Humanity. Possible reasons for both gender and cultural differences are speculated and discussed, and directions for further research are outlined.