How To Have A Difficult Conversation With Almost Anyone

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Recently, one of my friends deeply hurt my feelings.  Instead of talking with her about it I tried to ignore how I felt.  It didn’t take me long to begin seething on the inside.  I struggled to think kind thoughts.  I began to rewrite the long wonderful history we’ve had as friends with a negative spin.

Have you ever been there?  I think we all have been offended or hurt by someone we care about at some point.  It can be really hard to just let it go.  

In my situation, I love my friend, and I want to keep our relationship alive and healthy.  I knew that if I didn’t deal with this well our friendship could fall apart.  

Here’s how I did it…

  1. So I began to notice the ways I handled similar situations poorly in the past.  

  2. Then I began to construct a new plan that I felt would achieve the desired end result…that is what I outline here for you.

  3. Then I tested it in a few different situations.

I’m going to share the results with you here and a few possible places you could get stuck.  My hope is you will be able to reconcile with the people in your life and use the tools here to build the life of joy and connection you really want.

I was shocked by how easy it was to forgive after having this format for a healthy conversation.  As soon as I did it a huge weight was lifted off my shoulders.  I couldn’t believe it!  

But I want you to understand that this doesn’t just apply to friendship.  It will help you in all your relationship conversations.  As you learn this I am confident that you will find your personal voice and assertiveness will become second nature for you.

Here’s where I was getting stuck…do you relate to any of these?

Normally, In situations like these, I would do my best to minimize the hurt feelings by trying to ignore them.  You know the “go along to get along” method or the “grin and bare it”.  But I would struggle with resentment and passive aggressive tendencies….that certainly wouldn’t lead to a loving friendship.

Sometimes I would rehash it over and over with my husband or another friend.  But it never seemed to really solve things.  I never really felt all that better.  In fact, I would feel more bitter and the anger would intensify.  Sometimes I would take it out on my husband or in completely unrelated situations.

I would sometimes try to explain away their actions.  “They didn’t mean it” or “why am I so upset…I need to get over this”.  I would be basically minimizing my feelings…stuffing them…avoiding them.

I would pray and ask for healing.  Sometimes I would pray for God to open their eyes so they would initiate a healing conversation.  But that just didn’t happen very often.  

Sometimes I would cut my friend out of my life.  This is such a sad and difficult way to live.  It seemed easier just to avoid the person then to deal with the possible hurt again in the future. 

But the biggest problem is everyone is bound to hurt our feelings at some point because we’re human.  Humans can be a little dense and self-absorbed…me especially!  If we cut off everyone who hurts our feelings then it can become very lonely very fast.  

It’s even harder (sometimes impossible) when we try to cut out family members or our spouse.  It seems that the bitterness, anger, and resentment are worse because the pain is so much more deep.


The new plan…


I decided what I really wanted the end result to look like.  Did I want the relationship to stay in tact or did I want them to stomp away mad?  Did I want the friendship to grow even deeper or did I want to be blocked on all social media and never invited to their parties ever again?  

Side note:  It can be hard to want a positive outcome if the feelings are still really raw.  We can get stuck in the “wanting them to suffer since we are” rut.  This is a trap I’ve fallen into many times.  In this situation I have found it helpful to begin to see them in a different light.

I personally will begin to pray for them.  It’s really hard to ask for their greatest well-being to come about AND continue seeing them as a terrible enemy.  

If you don’t do prayer…then begin to consider their perspective.  Could they be hurting right now?  Could they be stressed?  Could they be depressed?  What is going on in their life that could have caused this poor behavior?  

Maybe they are simply ignorant of how they come across.  Maybe they were never taught.  Maybe they never had a tuned in or loving parent to help them grow in this area.  As you can say, “how sad for them”…you are now coming to the right state of mind for the next part.


I began to write out all that was bothering me about this situation.  As I journaled I began to sift out truth from just my anger speaking.  I would write out the scenario scene by scene and what bothered me about that scene until it made more sense.  Not only did the events make sense but I was also able to identify my real core emotions.  

In the situation with my friend I mentioned earlier, at first I thought the real source of my pain was that I was being passed up as a leader in our small group she led.  At first, the meaning I gave to that was maybe I wasn’t good enough and the other part was that she didn’t care about our friendship as much as I did.  

But as I dug deeper I realized that I really didn’t care about being a leader necessarily…I felt more hurt that she didn’t talk with me about what she was planning to do with the very small group I had spent every week participating in for the last 2 years.  I felt that I didn’t matter to her and that hurt because I value our relationship.

So now I have the root of my real concerns.  As you write it out things can become clearer for you.  Now you know what matters to you so you can have clearer words to express the feelings you have.  

It now becomes easier to consider their position in all of this.  I began to look at it from her perspective.  This part will also become clearer as we go along…because you can’t read their mind.  You really need to hear from them what’s really going on in their heart as well.


Here I began to reach for what I thought could have been going on in her mind.  I began to realize that she had a strategy and she probably just didn’t think to talk with me about it.  I didn’t fully understand her reasons…but those would become clearer later…and was probably the source of why I couldn’t just drop the matter entirely.

Side note: journaling is sometimes all you need to feel better.  You may not even need to continue forward with the rest of this post at all if you feel like you understand everything.  You’ll know if this is you though because the hurt feelings will lift.  But if you still feel unsettled then read on!

Approaching your loved one….

This part is really important because the way you approach your friend or loved one will make a huge difference in whether you reach your goal to keep the relationship in tact.  The assumption here is that you do want to heal the relationship.  So my goal is to help you achieve that end goal of healing yourself and the relationship.

Ideally this is done face to face.  In person is best because you can read their reaction much easier.  But this has also worked for me over the phone.  I don’t know if it works well in email or text because I haven’t tried it…but my assumption is that if they can read ahead…like in an email…they may skip over too much of your true intention and tone.  Plus, as I am sure everyone knows by now…tone in texting is nearly impossible to gage even with the cutest of emojis.

Before I just call them up I would ask them if there’s a good time to talk.  For one friend in particular getting a text like “we need to talk” or even “hey do you have a few minutes to talk with me at some point today” would immediately stress her out to the max…so you might consider adding, “everything is okay…I just need to share something with you”.   

The goal here is to be considerate of where they are in the moment.  What’s happening for them and making sure the conversation has a chance to be positive.  You don’t want to catch them when they are putting their kids to bed or some other stressful time.  Give them a chance to sit down and relax so they can really focus on your conversation.

Here is the structure I found to be the most helpful as I approached my friend with this difficult conversation…

  1. Smile and approach with positivity.  A warm hug and look in the eyes makes a difference.  They need to sense that you are not angry with them or really that you are not about to attack them.  You don’t want to give your friend more of a reason to feel uncomfortable.  Keep your voice calm and friendly and relax your face. Side note: don’t do this while you’re angry.  Be sure that you’ve somewhat worked out the big angry feelings before having this challenging conversation.  As soon as you approach a difficult conversation they will naturally tense up…you don’t want to add to that.  The ultimate goal is healing.  

  2. How are they?  Ask about something you know is happening in their life right now.  One friend I had a conversation like this with was in the middle of moving so I asked how it was going.  Make sure to be honestly and genuinely interested in how they are doing.  So pause and listen.  Ask a follow up question or two.  You may find out that something really bad happened.  If you discover that then you probably should choose a different time to discuss your hurts.  Care about them more than yourself.  This is a long term relationship and think long term.  

  3. Transition to the subject at hand.  This can be most challenging because we can get caught in the details of the starter questions and our nerves can take over.  I’ve heard some people say the words, “hey listen”….that just didn’t feel naturally to me.  But for some it could work.  For me I said something like, “Well the reason I asked to chat today was we had a conversation the other day that I didn’t quite understand and I wanted to talk with you about it.”

  4. Address feelings.  This is important because most people never intend on hurting us.  Most people have the best intentions.  So we want to acknowledge that this is probably a misunderstanding and you love them so you want to clear it up.  I made sure to address my feelings AND remind them of the situation by saying, “my feelings were hurt in the conversation we had…or because of what happened during x”.

  5. Acknowledge intentions.  Here is the part of the sentence that is really important because they are probably feeling a mixture of feelings.  They may feel ashamed or saddened because they are just now realizing that they said or did something to hurt you.  They may feel guarded because no one wants to feel like they have caused someone to feel hurt.  So this is why you want to be very clear in the next part of the sentence, “I know  you are not the type of person who would intentionally hurt anyone so I am really just bringing this up because I care about our relationship and I am struggling with my hurt feelings.  I know you would want to know if I was hurt because you care about me too and would never intentionally hurt me.”  You will probably hear them say something like, “of course not!”  They may already begin apologizing…or they may stay quiet.  I had one friend become a little overwhelmed and needed to get rid of distractions so we could talk more intimately.  

  6. Disarm fears.  We have already done some of this in previous statements.  This will also take some time to get used to because you may not recognize some body language indicators at first.  As I noticed my friend sort of fleeing the conversation it dawned on me that she was probably overwhelmed.  She probably didn’t expect to have this conversation at all so she was a little surprised.  She needed a chance to calm and cool off even just a little bit.  But the one phrase that made a huge difference and immediately diffused the situation was, “this is not a confrontation…this is a conversation”.  She knew at that moment I was not attacking her.  She was safe.  Her amygdala could relax.  There wasn’t going to be an altercation full of accusations.  

  7. Share what you experienced.  I was able to say, “when you said x or you did y…I interpreted this as I was not good enough….or I didn’t matter…or that I love you more than you love me….or I care about this relationship more than you do.”  You could even say, “at first I thought this….but then as I gave it more consideration I realized that it was in fact a big misunderstanding…but I really need to know how you feel because I’m having a hard time getting past the hurt.  Hearing from you will really help me make sense of things better.”

  8. Listen then reflect.  Sometimes I would stop and pause.  You want to give them a chance to speak and reflect on what you just said.  Reflect back what you’re hearing just in case there need to be clarification by saying, “I think I understand what you’re saying…are you saying…”  Then if you feel like you’ve been interrupted and need to discuss more or if they begin to ramble then bring the conversation back to the original topic by saying, “yes that makes sense…I also feel….xyz.”

  9. Be open.  There may be something that you’ve done to offend them.  If that’s the case then be prepared to take full responsibility for your part in the issues and apologize.  Then ask them how you can make things right.  Sometimes if you’re met with a return accusation then maybe they need your help modeling what you expect them to do for you.  Don’t get angry.  Model what you hope they will do for you so you can both get closure.  More than likely, if their defenses are gone they will be able to apologize and can both move forward with the healing process.

  10. What now?  In some cases a resolution for change needs to occur.  Maybe you’ll want to say…”well next time I will do ___ to make sure this doesn’t happen again.”  Hopefully they will come to a resolution and maybe they will promise something…but you don’t really have much control over this part.  You’ll need to accept that you can’t control their part of the process.  You can only control yourself.  The goal here isn’t to change them…it’s to gain closure and healing for you and for the relationship.

When does this NOT work?

There are a few times where something like this may not work.  Sometimes it won’t work this way with strangers because you don’t have an established relationship with the person.  In that case, asking questions to gain an understanding of what they mean can sometimes help because you build trust and understanding that might lead to the healing you need.  

Another time when this may not have the immediate positive affect is when there’s been a big relationship injury like infidelity or some serious abuse.  In these cases counseling or coaching is going to be extremely important.  That’s how we can help you.  We also have a program called HEALING Conversations Blueprint that can really help as well.

This can also be very difficult if your friend is unwilling to acknowledge your feelings.  If they shut down and pull away this is a sign that they are struggling with something that probably has very little to do with you.  If the hurt is really deep you may consider counseling or coaching to work through this wound.  

This post also assumes that you are having a conversation that you initiate with someone who has hurt you but probably unaware of what they’ve done.  So the approach might be a bit different if they surprise you with a difficult conversation.  

Or another possible problem could be if they just don’t care at all that they hurt you.  In this case…maybe they aren’t a very good friend after all.  But before jumping to a conclusion like that one be sure to have the necessary conversation.