This chapter moves away from traditional approaches to the study of illegitimacy by framing it as a varied and complicated phenomenon that resulted from a range of consensual and non-consensual sexual encounters between men and women across the social spectrum. The first part of this chapter examines the diverse sexual encounters and relationships that cannot be attributed to courtship. This evidence is used to engage with hypotheses such Laslett’s ‘bastardy prone sub-society’, and theories attributing higher levels of illegitimacy to cohabitation and irregular marriage. Evidence of sexual encounters such as rape, incest, adultery, prostitution and casual sex with no pretense of marriage is also explored. The second part of this chapter analyses the socioeconomic backgrounds of parents. Rather than being drawn exclusively from a single, impoverished sub-society prone to bearing and begetting illegitimate children, the mothers and fathers of illegitimate children in Wales had diverse occupational and social origins that reflect the diversity of Welsh society at the time. Evidence of socioeconomic diversity challenges the assumption that poorer individuals were at greater risk of bearing illegitimate children. This chapter argues that the link between illegitimacy and poverty is better understood as one of effect rather than a cause.