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He’s your friend, and he’s a good one. He supports you when you’re down and he’s got pretty good jokes. But there’s often an edge to him. It could be a comment about women or sometimes those jokes can a little too real. There’s a hostility that pops up that’s unnerving and you want to call him on it.

But you hesitate because you wonder if …

Stop. Yes, it’s your place. There are three things to remember when you think about calling out a friend for saying something dumb or offensive: This is what a good friend does. An issue exists, and silence will not make anything better.

Silence, of course, is hard to break. Guys can get uncomfortable bringing up problems. It can lead to conflict and potentially ending the friendship. The real stumbling block is that you’ve probably never done this, so the red-light message in your head is, “I’m just not sure I know how to trust myself to do it,” says Sam Cangelosi, a licensed therapist in Austin, Texas.

But it’s not a reason to retreat. In what’s been edited for length and clarity, we asked Cangelosi to lay out the best way to call out a friend, how to avoid any potential landmines, and why the most important thing to get across is that “it’s about the friendship. It’s not about the person, even though the behavior comes from the person.”

Calling out a friend can feel tricky. If you wait for a moment when something happens, it’s fresh, but you’re just reacting or you’re not being thoughtful. If you wait, you lose the momentum and the risk is your friend says, “Why you bringing this up now?” So if you’re going to do it, how do you do it?

Any important relationship is always occurring in some context. If something happens live, and others are present, it may be not the best time to bring it up for fear that the person would be embarrassed, in which case it would be very, very difficult for that ensuing conversation to be constructive in any sense. Then it’s a matter of determining the best time to bring it up in private.

But let’s say no one else is around. The friend with the concern has to ask himself, Am I in a good place to present my objection in a way that still is respectful, not an attack. [It’s saying,] Here’s what I just observed.

The other important step is to listen and be able to ask questions. It gives the opportunity to get more information as to what’s going on, and to acknowledge that and go, “I appreciate you sharing that with me. I realize where you’re coming from and I’m glad we’re talking about this, because I really would like for our friendship to not continue to include this kind of behavior.”

For someone taking this step, they might be going into unchartered territory because maybe they haven’t done this that much. How does one know that it’s gone okay?

You know based on what is happening in real time, and you can validate what you have in that moment. That’s important. What you don’t know is whether this will carry forth as a change in the person’s behavior.

If this person took the objection seriously, that would be evident going forward. If, on the other hand, a friend forgets or reverts back, the friend with the concern has to determine if its worth it to reengage with the issue.

The odds are pretty good that the answer is, “Yes, because it’s still there and it’s objectionable enough that I don’t wish to ignore it.” And so it could be offered as a reminder. “So where are we with this now? Because I really appreciated the great conversation we had about this. Can we just reengage in this?”

Acknowledging that there’s no one way to say anything, what should guide someone when they bring it up?

The emphasis is on the importance to the relationship. It’s not, “I’m objecting to your behavior and this is on you and you need to change.” Instead, it’s, “Our friendship is very important that I want to bring this to your attention. Because if we can address this and have some change occur, this helps us have an even better relationship.” It’s about the friendship. It’s not about the person, even though the behavior comes from the person.

“So it’s about us. And I want this to be a positive relationship, where we can be honest with each other, respect our different points of view, including being able to bring up things that either one of us is concerned about. And I will count on you to do the same with me.”

Of course, someone can say everything in the best way and the other person can still react poorly to the ask. What’s important to keep in mind?

Even if it’s presented well, he’s going to be uncomfortable. Something that could help is validating any small positive behaviors that occur during the conversation.

It’s being able to say, “Hey, I just want to know I really appreciate that you and I are in a place where you are willing to hear me out on this. I know this is not easy for either one of us.” Or just the simple, “I really appreciate you listening to what I’m saying here. Hopefully we can continue to talk this through.”

And then, if it turns out well, a week or month later, saying, “Hey, I’ve been thinking about that tough conversation that we had. I just want you to know I’m still appreciating you for being willing to talk.”

Reinforcing the effort to make positive change reinforces the friendship and leads to a better prospect for a good outcome longterm.