The 2.5 generation refers to individuals who have one parent born in the United States and one born in another country. The presence of both native-born and foreign-born parents has the potential to enhance bicultural adaptation. Across two studies with Latino young adults, we examine the extent to which the 2.5 generation is distinct from members of other generations with regard to cultural orientation, acculturative stress, and parent ethnic socialization. Results suggest that the 2.5-generation individuals report greater native cultural orientation, ethnic identity, and parental socialization compared with third-generation individuals, along with greater American orientation than first-generation individuals. The 2.5 generation also reports less language use and more acculturative stress due to Spanish competency pressures than first- and second-generation individuals. These results demonstrate that the 2.5-generation individuals may have some bicultural advantages compared with third-generation individuals; however, they may also experience similar challenges with regard to language maintenance.