Using a sample of 248 males and females from The Netherlands, we study the effect of criminal offending on union formation and union dissolution. Criminal and relational careers of high-risk respondents are analyzed using a long observation period (age 12 to age 36). Findings for men support the hypothesis that past criminal offending reduces the likelihood of being involved in a romantic relationship. Furthermore, male's past violent offending increases the probability of being single. Analysis of union dissolution for males showed that only recent violent offending is associated with the termination of a romantic relationship. Similar to our findings for men, findings for females show that the likelihood of being involved in a romantic relationship is negatively associated with past criminal offending. Moreover, it is an extended cumulative history of property offenses that significantly increases the likelihood of being single throughout the observation period. For women, recent offending significantly increases the probability of separation/divorce.