How to Have Difficult Conversations with People You Love


Tips for Approaching Difficult Conversations with People You Love

With the holidays around the corner, many people are experiencing a combination of excitement and nostalgia for the festive season along with the sting of unresolved or unexpressed challenges with people we love. For some, this can lead to a sense of anxiety or dysphoria as the holidays approach due to feeling stuck and uncertain about how to proceed.

Saying or hearing the words, “We need to talk,” often provokes feelings of uneasiness, mainly because these words acknowledge the elephant in the room: Something is unresolved and needs to be addressed, and because it is unresolved it remains uncertain. Uncertainty is an emotional state we as humans are not huge fans of, so our natural inclination might be to respond with pre-emptive defensiveness or the belief that we are right in an effort to create certainty and stability, and perhaps also preserve our egos. Add to this the fact that we all have beliefs about conflict and confrontation that were shaped by our past experiences and cultural backgrounds, so for many people these words might also elicit feelings of fear, dread, and perhaps the tendency to avoid conflict in order to keep the peace.

But what if speaking or hearing these words could be reframed as a need for connection, closeness, and deeper understanding? Oftentimes we need to share our perspective, clear the air, or let someone know how we feel in order to engage in our relationships with greater authenticity and richness, and having difficult conversations – whether we are the confronter or the one being confronted – is a crucial element to relational depth.

If there’s a difficult conversation or issue on your mind that you’ve been avoiding, whether you choose to approach it before the holidays or mentally bookmark it for a later date, consider the following tips for effectively and respectfully expressing your point of view:

Prepare Yourself

So much of a difficult conversation is how you prepare for it ahead of time. Try to remain reasonable and balanced in your expectations and let go of wording and rewording things in your head ahead of time with the goal of convincing the other person you’re right. Instead, ask yourself these questions to gain greater clarity into your perspective:

  • What is the purpose or goal of this conversation?
  • What is my ideal outcome? What are my wants and needs?
  • What am I feeling about this situation as a whole?
  • What part of the conflict or issue am I responsible for?
  • Is there anything from my past being triggered by the current issue? If so, what?
  • What assumptions do I have about the other person’s intentions or perspective? What might they be thinking and feeling?
  • How am I feeling about having this conversation? How might the other person be feeling?

Practice techniques for self-soothing and centering ahead of time, that way they can be leveraged in the moment when you need them the most. If you’re feeling nervous about approaching the conversation or find yourself playing it out in your head, that’s a great time to practice mindfulness, deep breathing, or grounding techniques, which allow you to acknowledge your emotions and return to the present moment.

Set a Time and Place

Neuroscience research on multitasking has shown that it’s nearly impossible to attend to multiple things at once, so state your need to discuss something and work with the other person to find a good time when neither of you will be distracted:

“I’d like to talk to you about ______ and am wondering if you have time on Tuesday evening for us to sit down together.”

It’s also important to consider the physical space you’re in when approaching difficult or sensitive topics. Whenever possible, try to schedule your conversation for a quiet space that is relatively private to reduce any environmental distractions. If finding time and space is difficult, try not to become discouraged. For things that are important to address, finding the right time and space can be worth the wait. That said, there is no “perfect” time or situation that will guarantee the other person will have a positive reception to the conversation.

Get Started by Raising the Issue

This is the part many people often struggle with the most because raising a concern entails direct communication, emotional vulnerability, and the potential for conflict. In addition, many people are concerned about likeability and may also fear the uncertainty of the other person’s reactions. Consider the following strategies as you broach the subject you’ll be discussing:

  • Approach the other person with curiosity, openness, and a collaborative mindset.
  • Be clear and use specific examples while avoiding blaming or using accusatory language. State what you notice and try not to use absolutes like “always” and “never” as you give examples.
  • Communicate from the place of feeling. Try to give the other person the benefit of the doubt by acknowledging the difference between intention and impact: “I felt _____ when you _____. It’s likely this wasn’t your intention, however this was the impact on me and I wanted to let you know so we could clear the air.”
    If you become nervous, practice self-soothing and centering.

Seek to Understand and Collaborate

  • Consider the following tips for working towards mutual understanding, respect, and resolution:
  • Elicit the other person’s perspective and listen without interrupting.
  • Acknowledge their experience. This is different than agreeing with them. Show that you understand what they’re saying: “What I hear you saying is _____. Is that correct? It’s important for me to really get where you’re coming from, even if we don’t see eye-to-eye.”
  • Own your role in the conflict, even if it’s small: “When you said _____ I felt hurt and could tell I became defensive so I don’t think I was entirely open to what you were saying. I’ll try to be more open in the future and let you know how I feel in the moment.”
  • Redirect the conversation if starts to go off the rails. “I think we might be getting into the weeds here and would like to refocus on the issue at hand.” Center yourself and breathe.
  • If the conversation gets heated, it’s okay to set boundaries by agreeing to revisit the issue with cooler heads: “I’m not comfortable with the direction this conversation is going and think it’s hard for us to have a productive dialogue while we’re both so upset. Let’s revisit this later.”
  • Again, use your self-soothing and centering techniques as needed.

Brainstorm Solutions

  • Start by asking for the other person’s ideas: “I think we have a solid understanding of where we differ. Based on what we discussed, what are your thoughts are on how we can move forward and work through this issue together?”
  • Again, listen to their ideas openly and without interrupting.
  • When sharing your ideas, use collaborative language whenever possible (e.g., “we/us” instead of “you/me”).

Wrap It Up

Recap what you’ve discussed, including solutions you’ve come to and areas where you may have agreed to disagree.
Express your appreciation for taking the time to discuss something that’s important to you, and share how doing so has impacted you: “I’m really glad we took the time to discuss this today. Even though we agreed to disagree on some things I feel like we each better understand where the other is coming from. This gives me hope that we can continue to discuss difficult things in the future so they don’t negatively impact our relationship.”


For especially difficult topics or if a conversation did not go as you hoped, it will be important to enlist the help of your support system. Reach out and debrief with a trusted friend or your partner. Again, practice self-care strategies and give yourself time and space to tend for yourself as you process and integrate this experience.


The Flip Side of the Coin

Sometimes people approach us with difficult topics and we find ourselves having negative reactions to being confronted. We may become nervous, defensive, or rigid in our thought process, and may sometimes find ourselves triggered by past challenges. If you hear the words, “We need to talk,” the very same strategies described above can be leveraged to remain receptive, calm, and self-aware when someone else raises a concern.

If you find yourself struggling to approach someone in your life about an issue that’s important to you, or having difficulty when approached by someone else, counseling can help you dig deeper into the experiences that have shaped your attitudes about conflict and assertiveness, learn skills for self-soothing, and strategize a healthy path forward. Fill out our contact form or call us at 312-870-0500 to find out how the therapists at Bergen Counseling Center can help you prepare to have difficult conversations with your loved ones. 

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