This study meta‐analytically examined theoretically derived antecedents of both directions of work–family enrichment (sometimes labeled facilitation or positive spillover), namely, work–family enrichment and family–work enrichment. Contextual and personal characteristics specific to each domain were examined. Resource‐providing (e.g., social support and work autonomy) and resource‐depleting (e.g., role overload) contextual characteristics were considered. Domain‐specific personal characteristics included the individuals' psychological involvement in each domain, the centrality of each domain, and work engagement. Results based on 767 correlations from 171 independent studies published between 1990 and 2016 indicate that several contextual and personal characteristics have significant relationships with enrichment. Although those associated with work tend to have stronger relationships with work–family enrichment and those associated with family tend to have stronger relationships with family–work enrichment, several antecedent variables have significant relationships with both directions of enrichment. Resource‐providing contextual characteristics tend to have stronger relationships with enrichment than do resource‐depleting characteristics. There was very little evidence of gender being a moderator of relationships between contextual characteristics and enrichment. Lastly, meta‐analytic structural equation modeling provided evidence that a theoretical path model wherein work engagement mediates between several contextual characteristics and enrichment is largely generalizable across populations.