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EPISODE · Jun 15, 2026 · 20 MIN

HOW AND WHEN TO ASK A QUESTION

from Men Don't Know podcast · host CHRIS BOONE

How & When to Ask a Question | Men Don't Know Podcast On this episode of the Men Don't Know Podcast, Chris and Jess sit down for an honest conversation about one of the most overlooked skills in relationships, friendships, and everyday communication: knowing how and when to ask a question. Is there ever a wrong time to ask something that's been on your mind? Why do some questions lead to deeper understanding while others create arguments? Chris and Jess break down the importance of timing, intention, emotional awareness, and learning how to communicate without putting someone on the defensive. From relationships and dating to family, friendships, and personal growth, they discuss why asking the right question at the right moment can completely change the outcome of a conversation. They also explore the mistakes people make when they ask questions looking for validation, ammunition, or reassurance instead of understanding. If you've ever struggled with difficult conversations, felt unheard, or wondered why certain discussions always seem to go sideways, this episode is for you. Topics include: • The difference between listening to respond and listening to understand • Why timing matters more than the question itself • Questions that strengthen relationships • Questions that create conflict • Emotional intelligence and communication • Understanding before being understood • How to create better conversations and stronger connections 🎙️ Men Don't Know Podcast Real conversations. Real perspectives. No filter. #MenDontKnowPodcast #Relationships #Communication #DatingAdvice #Podcast #HealthyRelationships #SelfGrowth #EmotionalIntelligence #ConversationSkills #JessAndChris

Episode metadata supplied by the publisher feed · Published Jun 15, 2026

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