This study examined the association between family structure history and adolescent romance. Using a national sample drawn from Add Health (N = 13,570), family structure at Wave I was associated with the likelihood that adolescents were involved in a romantic relationship at Wave II and, among those in a relationship, the number of relationships they had since Wave I. Cumulative family instability and its timing were also associated with these outcomes and largely drove the family structure effects. Gender and age interactions suggest that experiences of family instability were more consequential to the romantic lives of boys and younger teens.