Federally funded Healthy Marriage Initiative HMI) programs provide marriage education as well as other services to low-income diverse individuals and couples at many points along the marital continuum with improving childrens well-being as the overarching purpose. These programs need appropriate measures of healthy marriage for couples with children that relate to well-being. Purposes of this research were to examine the factor structure of a healthy marriage measurement developed by Manpower Demonstration Research Corporation MDRC) and how it varied across a) gender, b) race African American and Caucasian), and c) marital status married and unmarried). An additional purpose was to test a measurement model, developed by Child Trends, Inc., in which healthy marriage is hypothesized to predict parenting and child well-being. This cross-sectional quantitative survey research included 343 Head Start parents 151 males and 189 females) involved in a marriage/relationship. Overall, the unidimensional healthy marriage measurement fit for both males and females and the addition of two marital virtues, namely forgiveness and teamwork, also loaded well on this measurement. The factor loadings were significant for both males and females and results of chi-square difference tests indicated that the factor loadings for the great majority of variables were invariant across gender. However, the factor loading for relationship stability ones assessment that their relationship is not in trouble) was larger for males whereas child commitment ones assessment of their spouse/partners commitment to their child) was larger for females. Path analysis demonstrated that the Child Trends, Inc. healthy marriage measurement model fit differed by gender and this was supported by further SEM analysis. The effect size for the direct path between risk and healthy marriage was significantly larger for females than for males. The effect size of this path tended to be greater for African American women and unmarried women. Results using fit indices showed that the fit of the measurement model was appropriate for the diverse sample. Mediation results revealed that for both males and females, healthy marriage partially mediates the effect that depression and stress have on parenting. For females, parenting partially mediates the effect between risk and childrens social competence as well as between healthy marriage/healthy relationships and childrens social competence. Findings demonstrate support for the Child Trends, Inc. measurement model that healthy marriage/healthy relationships may enhance childrens social competence through positive parenting. Study results may inform federal and state healthy marriage and family initiatives as well as marriage and relationship education in terms of program delivery and evaluation.