This research study explores the association between attachment in a romantic relationship and past familial emotional experiences. Familial emotional experiences included family differentiation and family violence; and family differentiation included the experience of affective involvement and intrusiveness. Stepwise multiple regression analysis was adopted. In addition, the different relationships between father and son, mother and son, and perceived parents were explored separately, and gender differences were also compared through regression analysis. The research sample included 480 participants (168 males and 312 females) who were in a relationship at that time. The research results yielded three conclusions: (1) overall, offspring-parent violence best predicted anxiety attachment in a romantic relationship, however the predictive power was low and varied by gender; (2) in general, perceived parents affective involvement best predicted avoidance attachment in a relationship; (3) for men, affective involvement on the part of perceived parents best predicted avoidance attachment in a relationship with low to medium levels of predictive power. Generally speaking, the fewer violent experiences in an offspring-parent relationship, the less anxiety attachment an individual would likely experience in a romantic relationship. Also, the more emotional connections between perceived parents, the less avoidance attachment an individual would likely have. In closing, the paper included additional discussions and addressed research limitations.