How To Have Amazing Conversations With Friends

I was speaking with a friend of mine, Benjamin, and we had such a wonderful conversation. Afterwards I wanted to share with you some things that we did which contribute to conversational awesomeness. Please be aware up front that this is not a guide of how to be vapid but rather to connect more deeply and honestly.

Curiosity and concern for your friend#

Originally I called because I was concerned about our nutrition. I wanted to find out what his goals and thoughts are about food. Not everyone appreciates when people show concern about them but it is a very loving act to show genuine concern for people who are close to you. We each need our friends and associates to be taking good care of each other and to help guide us towards health when we stray.

In the past I’ve definitely been met with contempt for showing concern for someone. I think people can feel embarrassed when confronted with a thought that their current course of action is not in line with their values or that that there is a good chance they will wreck themselves if they keep doing it. Showing concern is not something you would want to do for someone who always believes they are right and has demonstrated a lot of invincible ignorance or self destructive behavior. How could their actions be anything but perfect, right?

It was really nice to be able to explain to my friend Benjamin about some of my concerns for him but he also wanted to express his interest for me in the same way. The conversation could go back and forth with questions and we encouraged that. Rather than give into defenses we could speak about it rationally and learn more about our goals.

Checking with your friend about emotions#

Sometimes we can take a conversation in a direction that is unexpected or emotionally difficult. It can be hard to talk about for anyone involved. Interestingly enough there are some ways we can handle those difficult moments and it’s all very mature and shows discussion finesse.

“How are you doing with the conversation right now?”
“Are you okay talking about this?”

If our friend is getting really irritated or uncomfortable with where the conversation is going it can be very instructive for everyone but we don’t intentionally want to cause people more trouble than they can handle. It would show a lack of empathy or could even be harmful if we push past defenses and go into a subject that someone has no awareness of and worse if they are avoiding that topic.

At one point in the conversation we were discussing how women have treated us in the past. There is a particular thing our mothers did which was never admitting fault or changing their minds. We got stonewalled and could never forge a connection with those women because they were too busy clinging to irrationalities and the illusion of control. That position fills me with bottomless contempt and it shuts down a conversation which could otherwise connect people. Benjamin asked me what I was feeling in that moment and I told him honestly.

It was difficult to say but I felt like we were both harmed by our mothers in that way. Benjamin, being very mature, did not take my hostility as an attack on him but recognized that I was having difficulty in the conversation. He asked me more about it and we came to a greater understanding because he had the compassion and capacity for empathy.


The way I see each conversation with someone is that each of us is a contributor to the quality of the connection. As unique individuals we have different perspective in a greater understanding of events. We can each contribute to the success or failure of the conversation.

What is the goal of the conversation you’re having?
Do I want to briefly catch up with the person or have a long and deep conversation?
Am I missing that person?
Do I want some attention?

Those are all fine questions to ask yourself and the answer is okay no matter what you choose. It’s good to have some awareness of what you need and to give the other person some indication of that so each of you knows how to contribute. For example it can help clear up any confusion if I know ahead of time you want to vent so I’m not expecting that you want to catch up about what’s going on for me.

Wrapping things up#

There are a lot of ways to contribute to an amazing conversation. I hope you give it a try and connect with your friends in the way you want to. It really is a great thing to connect, be heard, and to know you matter to someone else.

Finally, when you want to go it’s a good sign of self respect and respect for the others if you can say when you want to bring it to an end. Nobody wants to stay on longer than they are comfortable and you might find that people appreciate your honesty very much when you speak your need to go.

Enjoy your life with great conversations!

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