Dealing with Difficult Relationships

03.07.2024 |

Episode #10 of the course Mastering your relationships by John Robin


Welcome back!

In the first 9 lessons of this course, we have explored how to initiate and thrive in the relationships that interest us. We started with most relevant, such as family, intimate partners, and friends, and worked our way to less relevant, such as casual friends, acquaintances, and extended acquaintances. We even explored how to break the ice with strangers!

Thus far, we have focused on people who you want to know. Now, to finish the course, we’ll turn to the final domain: people who you know but might wish you didn’t.

Let’s put everything together with a final lesson on difficult relationships.


Difficult Relationships: Practicing Radical Kindness

There’s a reason I saved this type of relationship until last.

Dealing with difficult relationships will require many of the skills we’ve picked up in the previous lessons:

• Other-orientation from lesson 2

• Deliberate presence from lesson 3

• The “new-mapping” technique from lesson 4

• The simple comment technique from lesson 8

• The interviewer technique from lesson 9

Though it’s great to focus on the relationships you want to invest time in, it’s also important to learn how to handle difficult relationships, because usually they aren’t optional. Fortunately, though, all the skills you’ve learned in this course can come to your aid.

Perhaps there’s a toxic nephew you’re forced to see at family dinners. Perhaps you have a coworker who hates you and is kind to your face while gossiping behind your back. Perhaps there’s a spouse of a friend you find truly obnoxious. Perhaps you have a friend group you enjoy that comes with one particular friend you never get along with.

Whether you like it or not, you’ll have to deal with difficult relationships, and while there are many tips on how to deal with them—I could write a whole course on that topic alone!—fortunately there is one very powerful tool you can use to master even these kinds of situations.

The tool is called radical kindness.

Radical kindness is the practice of building bridges across differences, even when kindness might not be your natural first response. The purpose of radical kindness is to develop solidarity, find common ground, and promote social connection where isolation and conflict are the more likely result.

Here’s a few things, though, that radical kindness is not:

• It’s not becoming a doormat so you can let that person walk all over you

• It’s not putting on a smile and hiding your anger

• It’s not avoiding conflict and pretending to like that person when you really want to tell them off

Using radical kindness in your difficult relationships is ultimately meant to help you focus on preserving your own energy and pick your battles with care. Is it worth it to get into shouting matches with your toxic nephew at family gatherings? Is it worth it stewing over the passive-aggressive comments that a gossiping coworker makes? Is it worth canceling hangouts with your friend because their obnoxious spouse will be there too? Is it worth avoiding your friend group because of that one person you don’t get along with?

No to all of these!

Radical kindness should be treated like an antidote for how to remedy your emotional well-being in those difficult relationships you can’t avoid. Try it! You’ll be surprised. Practice the “new mapping” technique with your nephew, then when his birthday comes around, buy him a thoughtful birthday gift based on learning more about what truly interests him. Practice deliberate presence with your gossiping coworker whenever you’re interacting with them. Use the simple comment technique to make small-talk. Develop other-orientation with your friend’s obnoxious spouse, rather than just ignoring them and stewing in private resentment. Use the interviewer technique with that person in the friend group you don’t get along with.

Practicing radical kindness softens the relationship with these difficult people. Having a non-judgmental, non-combative orientation can disarm quite a few conflicts that are likely to arise. The relationship, at the very least, becomes more neutralized.


Tip of the Day: Creating the Endships Orientation

In my other course, Mastering Your Conversations, I mentioned the concept of an endship. An endship is a friendship you’ve chosen to end.

There’s one thing unique about an endship: you don’t actually sever the relationship. Instead, you take an inner standpoint on the given relationship that you are going to stop investing actions, and even thoughts, in the relationship. To you, it has “ended” and any interaction with that person is purely an act of congeniality.

When practicing radical kindness in your difficult relationships, I recommend taking an endship orientation. The reason you’re being kind to them, and not fighting back against toxic or cruel behavior, isn’t because you’re a doormat or a conflict avoider, but simply because the relationship has ended to you. You have nothing further to invest in it, other than just being an example of a good human being.

And that’s a good way to wrap up our course. You’re now equipped to master the many kinds of relationships you might find yourself in. Now, go and practice and develop your rich social network—and set a great example for others.

I love hearing from my students. If you have any requests for future courses, or questions about this one, please let me know. Many of my best course ideas have come from these email conversations with students!

Reach out to me at:


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Recommended book

How to Deal With Difficult People: Smart Tactics for Overcoming the Problem People in Your Life by Gill Hasson


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