Youth, while tech-savvy and highly active on social media, are still vulnerable to online privacy and security risks. Therefore, it is critical to understand how they negotiate and manage social connections versus protecting themselves in online contexts. In this work, we conducted a thematic analysis of 1,318 private conversations on Instagram from 149 youth aged 13-21 to understand the digital privacy and security topics they discussed, if and how they engaged in risky privacy behaviors, and how they balanced the benefits and risks (i.e., privacy calculus) of making these decisions. Overall, youth were forthcoming when broaching a wide range of topics on digital privacy and security, ranging from password management and account access challenges to shared experiences of being victims of privacy risks. However, they also openly engaged in risky behaviors, such as sharing personal account information with peers and even perpetrating privacy and security risks against others. Nonetheless, we found many of these behaviors could be explained by the unique "privacy calculus" of youth, where they often prioritized social benefits over potential risks; for instance, youth often shared account credentials with peers to foster social connection and affirmation. As such, we provide a nuanced understanding of youth decision-making regarding digital security and privacy, highlighting both positive behaviors, tensions, and points of concern. We encourage future research to continue to challenge the potentially untrue narratives regarding youth and their digital privacy and security to unpack the nuance of their privacy calculus that may differ from that of adults.