This special issue of Journal of Personality, composed of eight original articles, attends to the intersection of intrapersonal and interpersonal processes. Articles adopt a contextual approach to personality with attention to the need to belong (and the lack thereof), self-presentation concerns and styles, sexuality, curiosity, self-regulatory strength and strategies, and dynamic methodologies and analyses to study people within relationships. In this introduction, we offer challenges and aspirational goals for personality science. In particular, we discuss the importance of context when conceptualizing and studying personality, the seduction of innovative methodologies and analytic procedures, and the value of focusing on people and heterogeneity in groups instead of simply variables. We hope that this collection of articles deepens personality science and reminds readers that to truly understand human beings, they cannot be divorced from their social milieu.