Why Difficult Conversations Are So Hard (And How to Make Them Easier)
Speech bubbles symbolizing relationship communication challenges, emotional expression, and navigating difficult conversations in therapy
You need to talk to someone about something hard, a boundary that was crossed. A feeling that was hurt. A pattern that's not working. Something that matters.
And you can't do it. You've tried to bring it up a dozen times. You've rehearsed what you'll say. But when the moment comes, you freeze. Or you start talking, and it immediately goes wrong. They get defensive. You get flustered. The conversation derails. And nothing gets resolved.
So you avoid it. You tell yourself it's not that important. That you're overreacting. That bringing it up will just make things worse. But the issue doesn't go away. It builds. And the longer you avoid the conversation, the harder it becomes to have.
Many people we work with in therapy across Illinois describe dreading difficult conversations and either avoiding them entirely or watching them blow up despite their best intentions. And they don't understand why something that should be simple—just talking to someone—feels so impossible.
Navigating difficult conversations is one of the most common communication issues people bring to therapy.
If you struggle with difficult conversations, here's what you need to know. It's not because you're bad at communication. It's because these conversations trigger specific fears and patterns that make them feel dangerous even when they're not. And understanding what's actually happening changes everything.
Why Difficult Conversations Feel Impossible
Difficult conversations aren't hard because of the topic. They're hard because of what you're afraid will happen:
You're afraid of conflict. You don't want to fight. You don't want tension. You don't want things to get ugly. So you avoid saying anything that might upset the other person. And in doing that, you never actually address what's wrong.
You're afraid of their reaction. What if they get angry? What if they cry? What if they shut down? What if they reject you? The fear of how they'll respond keeps you silent. Because staying silent feels safer than risking their reaction.
You're afraid you'll say it wrong. You'll be too harsh. Too emotional. Too unclear. You'll hurt their feelings when you didn't mean to. You'll make things worse instead of better. So you keep rehearsing in your head, trying to find the perfect way to say it. And the perfect way never comes.
You're afraid it won't matter. What if you finally say something and they dismiss it? What if they don't care? What if nothing changes? Then you'll have made yourself vulnerable for nothing. So it feels safer to just not try.
And you're afraid of what it means about you. That you're too sensitive. Too demanding. Too much. That needing to have this conversation means there's something wrong with you. So you talk yourself out of it before you even start.
What Makes Difficult Conversations Go Wrong
Even when you do manage to start the conversation, there are things that make it fall apart:
You lead with blame. "You always do this." "You never listen." "You don't care." When the other person hears blame, they stop listening. They get defensive. And the conversation becomes about defending themselves instead of hearing you.
You're vague about what you need. You hint. You talk around it. You hope they'll figure it out. But they don't. And then you're frustrated that they didn't get it. But you never actually said it clearly.
You bring it up at the wrong time. When you're already angry. When they're stressed. When there's no time to actually talk it through. Timing matters. And bringing up something hard when either of you is already overwhelmed sets it up to fail.
You make it about the past. You bring up everything they've ever done. All the other times this happened. All the ways they've let you down. And suddenly you're not talking about the current issue. You're rehashing every hurt from the last five years.
You expect them to read your mind. You think they should know why you're upset. They should understand what you need. They should apologize without you having to explain. But they can't. And expecting them to set both of you up for disappointment.
You shut down when it gets hard. The moment they react emotionally or push back, you retreat. You say "never mind," "forget it," or "it's fine." And the conversation ends without anything being resolved.
What Actually Helps
If you want difficult conversations to go better, here's what can help:
Start with what you observed, not what you assumed. Don't tell them what they were thinking or why they did something. Just describe what happened. "When you canceled our plans last minute," not "You obviously don't care about spending time with me."
Name how it affected you. Use "I felt," not "You made me feel." Take responsibility for your feelings while still expressing them. "I felt hurt and unimportant" is different from "You made me feel unimportant."
Be clear about what you need. Don't make them guess. "I need you to let me know earlier if plans change" is specific. "I need you to care more" is vague and unhelpful.
Stay in the present. This conversation is about this issue. Not every issue. If you start bringing up the past, you're not trying to resolve anything. You're just unloading.
Give them room to respond. You're not trying to lecture them. You're trying to have a conversation. That means listening to their side too. Even if you don't agree with it.
Stay with it even when it's uncomfortable. Difficult conversations are supposed to be uncomfortable. That's why they're called difficult. Don't bail the moment it gets hard. Stay. Work through it.
When Difficult Conversations Are Actually Unsafe
Sometimes the reason you can't have a difficult conversation isn't that you're avoiding it. It's because it's genuinely not safe.
If the other person responds to any attempt at conversation with anger, threats, or punishment, that's not a communication problem. That's an unsafe relationship.
If you've tried to bring up issues and they consistently dismiss, gaslight, or turn it around on you, that's not a skill issue on your part. That's someone who isn't willing to hear you.
And if you're terrified of their reaction, not because you're anxious but because you know from experience that they'll make you pay for speaking up, trust that. That's not a conversation problem. That's a safety problem.
Difficult conversations require two people who are willing to listen. If you don't have that, no communication technique in the world will help.
Why Avoiding Difficult Conversations Makes Things Worse
When you avoid difficult conversations, here's what happens:
The issue doesn't go away. It festers. It builds. It shows up in other ways. You get resentful. You pull away. You start fights about unrelated things because you can't talk about the real thing.
You lose trust in yourself. Every time you don't say something you need to say, you send yourself a message: your feelings don't matter. Your needs aren't important. You can't handle conflict. And that erodes your confidence over time.
The other person doesn't get a chance to change. They might not even know there's a problem. And by not telling them, you're robbing them of the opportunity to do better.
The relationship suffers. Because you can't have real intimacy without honesty. And you can't have honesty if you can't talk about hard things.
Getting Support
If you avoid difficult conversations because they feel impossible, if they always go wrong no matter how hard you try, or if you're not sure whether your relationship is safe enough to have them, therapy can help.
At Walk With Me Counseling Center in Chicago, we work with people across Illinois through online therapy who struggle with communication, conflict, and difficult conversations. Our therapists are culturally responsive and can help you understand what's blocking you and develop skills to navigate hard conversations more effectively.
We offer free 15-minute consultations so you can talk through what's going on and see if therapy feels like the right support. Many people use insurance to make therapy more accessible, and we work with BCBS PPO and Aetna PPO.
Frequently Asked Questions
Why do I avoid difficult conversations even when I know I need to have them? Avoidance usually comes from fear—fear of conflict, rejection, or making things worse. Your brain perceives the conversation as dangerous, even when logically you know it's necessary.
How do I start a difficult conversation without it turning into a fight? Start with what you observed rather than what you assumed, express how it affected you using "I" statements, and be clear about what you need. Avoid blame and stay focused on the specific issue.
What if the other person gets defensive or shuts down? Give them space to react without immediately retreating. Stay calm, acknowledge their feelings, and try to redirect back to the conversation. If they consistently can't handle any feedback, that's important information about the relationship.
Is it normal to feel anxious before a difficult conversation? Yes. These conversations trigger vulnerability and uncertainty. Some anxiety is normal. Paralyzing fear that makes you avoid all hard conversations may benefit from therapeutic support.
When should I just let something go instead of bringing it up? Let it go if it's truly minor and won't build resentment. Bring it up if it's affecting how you feel about the person or relationship, if it's a pattern, or if avoiding it is creating distance between you.
Difficult conversations are hard because they require vulnerability, honesty, and the willingness to risk discomfort for the sake of connection. But avoiding them doesn't protect you or the relationship. It just postpones the conflict while the issue grows bigger. Learning to have these conversations, even imperfectly, is one of the most important skills you can develop. And you don't have to figure it out alone.
