Regina Spektor participates in "Ask a Grown Woman" for Rookie, addressing various questions from teenagers. She empathizes with a 16-year-old struggling to communicate with immigrant parents about everyday stresses, suggesting a conversation emphasizing the desire to benefit from their wisdom. Spektor encourages another teen unsure about their future career, advocating the importance of staying open to discovery and using one's unique talents. Addressing a senior's dilemma about a relationship with a freshman, Spektor advises considering the challenges of distance in a relationship and the value of shared experiences.