This paper tests for differences in reported life satisfaction between married and cohabiting persons, i.e. the cohabitation gap, and in particular whether selection factors can explain the cohabitation gap. The paper also explores whether age at marriage and at start of cohabitation as well as the duration of relationship type matters for subjective well-being. Based on statistical and regression analysis of the 2008 National Income Dynamics Survey, married and cohabiting persons exhibit some differences in their respective determinants of life satisfaction. While the age at relationship commencement has no relationship with well-being, there is evidence to suggest that married people become more satisfied at a later stage in marriage, while cohabitants are more satisfied initially. A significant cohabitation gap exists (0.251), but after controlling for various selection factors, the cohabitation gap virtually disappears (0.042) and becomes insignificant, which suggests that marriage and cohabitation are very similar in South Africa. Relative income, absolute income, and education explain the largest part of the cohabitation gap. Against the global backdrop of an increasing trend towards cohabitation and declining marriage rates, the overall results of this paper suggest that, since a cohabitation gap no longer exists after controlling for selection factors, South Africans may as well not go the “official route” of entering into marriage, as cohabitation provides similar benefits in terms of its contribution to individual satisfaction with life.