How to Have Difficult Conversations | LHS Classic episode artwork

EPISODE · Nov 24, 2025 · 58 MIN

How to Have Difficult Conversations | LHS Classic

from Love, Happiness and Success with Dr. Lisa Marie Bobby · host Dr. Lisa Marie Bobby

This time of year brings a lot of togetherness… and with it, a lot of unspoken tension. Difficult conversations are the ones you rehearse in your mind or hold back during holiday dinners, worried that saying the wrong thing could create a rift you can’t repair. That’s why I’m re-releasing this episode on how to have difficult conversations in a way that protects your relationship (and often deepens it) instead of pushing you further apart. We’ll talk about why we either avoid hard topics until resentment leaks out, or bring them up in a burst of anger and criticism, and how both patterns wear down trust over time. You’ll learn what it actually takes to do this differently: managing emotional flooding, getting honest with yourself before you speak, knowing when a conversation is worth having (and when it’s time to set a firm boundary), and shifting the goal from “winning” to mutual understanding so you can stay connected even when you don’t agree. Episode Breakdown: 00:00 Navigating Difficult Conversations 06:07 Emotional Intelligence & Self-Regulation 17:49 When to Set Boundaries and Walk Away 21:00 Growth Through Discomfort 27:05 Preparing for Hard Conversations 29:53 Seeing Through Others’ Eyes 36:08 Handling Polarized Views 42:09 Reciprocity & Healthy Relationships If this episode brings a specific conversation to mind and your stomach flips a little just thinking about it, I have a resource to support you. My Communication That Connects free training takes you deeper into the skills we cover here - practical do’s and don'ts for communication that creates understanding, plus real examples you can use with your partner right away. You’ll also receive a full workbook with lessons, activities, and homework to help you get to the root of conflict, calm reactive patterns, and build a more emotionally safe connection.  And if you’re at the point where you don’t want to keep doing this alone, I’d be honored to support you more directly. At Growing Self, you can tell us what’s going on in your life and relationships, and we’ll help you connect with the right therapist or coach on my team. It’s a simple, private way to say, “Here’s what I’m struggling with,” and get matched with someone who can walk through it with you. Start that process here: schedule a consultation. You deserve relationships where you can say the hard things, feel truly heard, and still feel loved at the end of the day. 💗 xoxo, Dr. Lisa Marie BobbyGrowing Self

This time of year brings a lot of togetherness… and with it, a lot of unspoken tension. Difficult conversations are the ones you rehearse in your mind or hold back during holiday dinners, worried that saying the wrong thing could create a rift you can’t repair. That’s why I’m re-releasing this episode on how to have difficult conversations in a way that protects your relationship (and often deepens it) instead of pushing you further apart. We’ll talk about why we either avoid hard topics until resentment leaks out, or bring them up in a burst of anger and criticism, and how both patterns wear down trust over time. You’ll learn what it actually takes to do this differently: managing emotional flooding, getting honest with yourself before you speak, knowing when a conversation is worth having (and when it’s time to set a firm boundary), and shifting the goal from “winning” to mutual understanding so you can stay connected even when you don’t agree. Episode Breakdown: 00:00 Navigating Difficult Conversations 06:07 Emotional Intelligence & Self-Regulation 17:49 When to Set Boundaries and Walk Away 21:00 Growth Through Discomfort 27:05 Preparing for Hard Conversations 29:53 Seeing Through Others’ Eyes 36:08 Handling Polarized Views 42:09 Reciprocity & Healthy Relationships If this episode brings a specific conversation to mind and your stomach flips a little just thinking about it, I have a resource to support you. My Communication That Connects free training takes you deeper into the skills we cover here - practical do’s and don'ts for communication that creates understanding, plus real examples you can use with your partner right away. You’ll also receive a full workbook with lessons, activities, and homework to help you get to the root of conflict, calm reactive patterns, and build a more emotionally safe connection.  And if you’re at the point where you don’t want to keep doing this alone, I’d be honored to support you more directly. At Growing Self, you can tell us what’s going on in your life and relationships, and we’ll help you connect with the right therapist or coach on my team. It’s a simple, private way to say, “Here’s what I’m struggling with,” and get matched with someone who can walk through it with you. Start that process here: schedule a consultation. You deserve relationships where you can say the hard things, feel truly heard, and still feel loved at the end of the day. 💗 xoxo, Dr. Lisa Marie BobbyGrowing Self

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How long is this episode of Love, Happiness and Success with Dr. Lisa Marie Bobby?

This episode is 58 minutes long.

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This episode was published on November 24, 2025.

What is this episode about?

This time of year brings a lot of togetherness… and with it, a lot of unspoken tension. Difficult conversations are the ones you rehearse in your mind or hold back during holiday dinners, worried that saying the wrong thing could create a rift you...

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