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Let's Talk About It: Encouraging Difficult Conversations Between Generations

  • Writer: breshawna mccoy
    breshawna mccoy
  • Sep 24
  • 4 min read

Ah, the art of the difficult conversation. No one likes it, but everyone needs it. Whether it's talking about political views, family matters, or why you just can't stand the new generation’s obsession with avocado toast, opening up dialogue between generations is essential. In this post, we’ll discuss how to navigate these tough conversations with humor, grace, and a sprinkle of patience. Trust us—your future self will thank you.

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Why Do We Avoid Hard Conversations?

First off, let’s get real: hard conversations often feel like that one family member who insists on oversharing at every holiday gathering. You know you should engage, but it's tempting to retreat. But avoiding these conversations only leads to misunderstanding, resentment, and a whole lot of awkward silences. So, why do we avoid them in the first place?

  • Fear of Conflict: It’s easier to pretend everything’s fine than to address the elephant in the room.

  • Generational Gaps: What feels like "common sense" to one generation might sound completely foreign to another.

  • Emotions Run High: Some topics, like politics or family matters, can trigger intense emotions, and no one wants to be the one to spark World War III at dinner.

The Benefits of Having Tough Talks

  1. Deeper Understanding: When we open the door to tough conversations, we invite understanding. Generational differences often stem from different experiences, so having these dialogues helps bridge the gap.

  2. Clearer Expectations: Instead of assuming what the other person thinks or feels, you get the facts. It’s the difference between assuming Aunt Linda doesn’t care about your new job and hearing her say, “I’m proud of you, but I also need to stop using my flip phone.”

  3. Growth and Change: Discussing uncomfortable topics can be a catalyst for growth—both for individuals and relationships. Change often comes when we challenge outdated beliefs and norms.

  4. Strengthening Relationships: When we approach conversations with empathy, we’re able to strengthen our bonds. It’s not just about talking—it’s about listening too.

How to Have Effective and Respectful Conversations

  1. Listen First, Speak Second Sounds simple, right? But really listening—without interrupting, judging, or waiting for your turn to speak—is a skill that’s often overlooked. This allows the other person to feel heard and respected, which makes the conversation much smoother.

  2. Set Boundaries Let’s face it, some conversations can get heated. If things are spiraling into an argument, it’s OK to take a breather. Setting boundaries on what’s acceptable in terms of tone, language, and timing is essential to maintaining respect.

  3. Find Common Ground Even in the most heated of debates, there’s usually a kernel of commonality. Whether it’s the desire to see your family happy, or the hope for progress in society, remind each other that you’re on the same team—just with different playbooks.

  4. Acknowledge the Differences You don’t need to agree on everything, but acknowledging each other's views helps build understanding. “I see where you’re coming from,” or “I hadn’t thought of it like that” can go a long way in diffusing tension.

Making It Relevant to African American Communities

Generational conversations in African American families often carry deeper layers, shaped by shared history and struggles. From the older generation’s experiences with segregation and civil rights movements to the younger generation's challenges in navigating systemic racism today, these conversations can be uncomfortable—but they’re necessary for progress.

  • Preserving History: The older generation carries stories of resilience, struggle, and triumph. Younger generations can learn from this history, but only if it’s passed down openly.

  • Navigating Change: Younger generations are experiencing a different world, but sometimes the lessons of the past can still guide the future. These conversations help prevent the old adage of “history repeating itself.”

  • Generational Trauma: Sometimes, these difficult conversations are about healing generational trauma. Being able to talk openly about pain and hardship is a critical step in breaking cycles of hurt.

Fun (And Maybe Awkward) Tips for Talking Across Generations

  1. Use Humor to Lighten the Mood Let’s face it, sometimes humor is the grease that helps the gears of difficult conversations turn. If your grandma thinks texting is still “magic,” joke about it in a way that makes her feel included, not embarrassed. Laughter can break down walls and help people feel more comfortable.

  2. Start with “I” Statements Rather than saying, “You always interrupt me,” try something like, “I feel unheard when I don’t have the chance to finish my thought.” This takes the pressure off and focuses on your feelings rather than placing blame.

  3. Bring It Back to the Positive If a conversation starts going south, try to bring it back to a positive place. “We may disagree on this, but I know we both care about [family/community/etc.]. Let’s agree to disagree for now and come back to it later.”

The Art of Patience

Remember: you’re not going to change someone’s worldview in one conversation, and you’re certainly not going to convince your grandparents to join Twitter overnight. Patience is key. Not only with the person you’re conversing with, but with yourself as well. Sometimes, it takes multiple discussions to get to a place of mutual understanding.


Having hard conversations is like learning to dance: It takes practice, patience, and a willingness to trip over your feet a few times. But once you find your rhythm, it’s a beautiful thing. So, grab your family, set the stage for an honest conversation, and let the music of understanding fill the room. The dance may be awkward at first, but it will be worth every step.

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