Five shocking ways to combat the teenage dead end conversation. We have all experienced these dreadful teen responses to what we thought were more than appropriate questions: Fine. Good. I don’t know. And, then there are the exasperated sighs or silent shrugs or worse, challenging glares. For most, this can feel like the conversation has reached a dead-end. I frequently wonder how it is possible that in just over a decade of living, tweens and teens have mastered the art of ending conversations while making you feel like a burden. For the more persistent, you may attempt a second round of conversation if you dare and ask, “What do you mean you don’t know?” This usually triggers the disgusted eye roll.