Never married parents (NMPs) are a burgeoning population within the Family Court system. However, there is no empirical research on these parents' separation process, though the neighboring literature purports that NMPs are more at risk for negative child wellbeing outcomes than their divorcing counterparts. This study investigated child behavior problems in high conflict litigating never married families by assessing four salient issues collectively termed chaotic environment: economic strain, lack of social support for the parents, parental repartnering, and family relocation, which included parent changing residence and child changing schools. They were then compared to divorcing parents. It was hypothesized that NMPs would experience higher levels of chaotic environment, and subsequent increases in child behavior problems than divorcing parents, but that the relationship for NMPs and divorcing parents would be the same with each of the chaotic environment variables. This study found the contrary. NMPs only had significantly higher mean scores on lack of social support for fathers and marital status did not predict child behavior problems. Both economic strain and child changing schools predicted child behavior problems for both mothers and fathers. Two interaction effects with mothers were found, indicating that the more a never married mothers repartnered and/or changed her residence, the more behavior problems her child had, while divorcing mothers experiencing the converse effect.