5 Ways to Have a Difficult Conversation In 2023

Tonight I have to have a difficult conversation with my boyfriend. I am dreading it. I am sitting here thinking about what to say and what he is going to say and how he could hate me, maybe even break up with me, by the end of it.

The life coach in me knows that while my concerns are real there are many approaches that I can take that will allow us to have a successful conversation, one we will both walk away from in the best way possible.

What can I do to ensure that the conversation is a good one?

#1 – Let go of assumptions.

As I sit here thinking about what tonight is going to look like I am visualizing all sorts of reactions from my boyfriend around what I am going to say. Some are calm, some are angry, and some involve tears.

And they are all that I can think about more even than the talk’s content. I just don ‘ t know what will happen and it worries me.

But I have to let go of those projected outcomes. I have NO IDEA how he is going to react and to spend even one minute perseverating about what they might be is a complete waste of time.

So, I let have to let them go and accept that whatever happens will happen and that I can’t control the outcome.

#2 – Choose a good time and place.

When my kids were little, and I had to discuss something difficult with them, I always chose to do it in one of two places: in the car or on a walk.

I have found it very effective to have conversations with someone side by side instead of face to face. I think that perhaps it makes each participant a little less vulnerable and gives them a moment more to react to a statement. The eyes can say so much, sometimes quickly, which can cause the conversation to devolve in some way.

I also always chose a time that was not stressful. Tonight my boyfriend is coming over for dog therapy, pizza and football. His top 3 things in this world. He will be happy, and then we will begin. Softly.

#3 – Don ‘ t attack.

Your goal in this situation is to have an effective, difficult conversation. One that lands on it’s mark and has a satisfactory end result. To do this it ‘ s important not to attack.

My boyfriend is struggling with a few issues in our relationship. I will ask him if he is happy. On a scale of 1-10, perhaps. Doing so will (gradually) get him to open up to me about what is happening. From there, I can ask him probing questions that will lead to us being able to discuss how to get us through those issues.

I will not say ‘ Why are you doing these stupid things over and over? ‘ I can guarantee that the only thing that will do is shut him down. And make him leave.

Not the end goal.

#4 – Be sure to listen.

This is so important. You must be very careful to listen to what you are hearing back from the person you are talking with. Not only could you get some valuable information, but by letting them know that you are paying attention, you will be more likely to get the outcome that you seek.

Try reflective listening. Many people find it difficult, but it really works. After they speak, say, ‘ I hear you saying that ‘ ¦.and I get it. ‘ Words that will allow them to feel heard, validated and empathized with. Often, all people want to be is heard and not feeling so makes them angry and makes them shut down or storm off.

Again, not the end goal.

#5 – Know that everything is going to be all right.

I know this conversation tonight with my boyfriend seems like it might be the end of the world, but really, no matter what, it ‘ s all going to be okay.

I always tell my clients to consider, ‘ What is the worst that can happen? ‘

For me, I know that the worse that could happen would be the death of my child. That I don ‘ t think I could survive. But you know what? I probably could. Regardless, that won’t happen tonight because of this conversation.

So, yes, a conversation might bring about pain and discomfort and maybe even produce some short, or long, term effects but really, everyone is going to be okay.

As I have mentioned before, pain is a part of the growing process. This conversation will be part of the growing process.

And growing is the end goal.

I am nervous about tonight ‘ s conversation. The topic is a difficult one, but the conversation is necessary. Now that I am done worrying about possible outcomes, I have my list of things I want to address and will do so carefully and with love.

And while there might be some tears and discomfort, I know that everything is going to be okay. We will still love each other and that life will go on.

You can do this. I promise.

If you have read this far you must be getting ready for a difficult conversation.

Reach out to me NOW and let me help you get the words out.

Email me at [email protected], or click here, and let’s get started!

Mitzi Bockmann

I am a NYC based Certified Life Coach and mental health advocate. My writing has been published on The Huffington Post, Prevention,  Psych Central, Pop Sugar, MSN and The Good Man Project, among others. I work with all kinds of people to help them go from depressed and overwhelmed to confident and happy in their relationships and in their world.