Based on observations that challenge the theory of cumulative advantage/disadvantage (CAD) which says that inequalities increase over time this paper formulates a new theory; the theory of conditional social equality (CSE). Based on observations, informal conversations and interviews at eighteen different Men’s Sheds in Denmark, New Zealand and Australia, we argue that inequalities between older men may actually decrease – but only on certain conditions, and not any type of inequality. In the current study we use a narrative approach to show how learning groups that were homogeneous age and sex helped erase class divisions, while divisions of ethnicity and sexual orientation remained firm. Other configurations of divisions that are challenged or not challenged are evident from other studies. The theory of conditional social equality (CSE) predicts the following: i) in-group homogeneity enables the acceptance of some aspects of heterogeneity, ii) some other aspects of in-group heterogeneity will not be tolerated, thus maintaining in-group cohesion, and iii), in-group homogeneity and boundary setting towards out-groups are prerequisites for the acceptance of (some) aspects of in-group heterogeneity. We invite other researcher to test the theory in learning groups of different configurations.