Modern Etiquette: Handling Difficult Conversations Online

by Grace Bonney


It’s been a while since I updated our Modern Etiquette column (3 years to be exact, yikes!). But every day when I log in to answer comments here, these posts are where people come back again and again to talk, debate and connect. That got me thinking about some of the communication hurdles we’re facing right now in our world and how even the most tense of topics can still be places we’re able to see, hear and understand each other.

So rather than rebooting this column with something light like gift-giving or housewarming gifts, I wanted to tackle the elephant in the room: starting, handling and compassionately ending difficult conversations online.

I’ve spent the majority of my adult life navigating difficult conversations online, from the casual troll commenter and vicious personal attacks to the occasional Twitter battle or social media meltdown. No matter who you are, some version of a tough talk will come your way online at some point, and I’ve found there are most definitely some do’s and don’t’s that can help you get through these moments with patience, kindness and respect. It doesn’t require Herculean strength or a psychology degree — just some basic guidelines that will help you connect with your online neighbor (and your in-person neighbor, too). The goal of these conversations isn’t to convert people to your way of thinking, but rather to find ways to communicate your personal stories so you can shine a light on the things you have in common (shared values, concerns, fears), instead of exacerbating the differences. Read on for my take on navigating the tricky world of tense online conversations… xo, grace

Illustration by Anna Emilia


Before we get started let’s lay down some ground rules:

  1. If someone threatens you, you have the right to walk away. No matter how compassionate you’re trying to be, if someone threatens you online* or uses language and imagery that is disrespectful (sexist, racist, etc.) you have the right to disengage, block them and move on. Yes, in an ideal world we’d engage everyone to find the root of that threatening behavior, but if you don’t feel safe, walk away. *And if anyone threatens you and your safety (or threatens to expose your personal contact information) report them to your local authorities and the report their threat to the platform you’re using (Twitter, etc.). Moments like that should not be taken lightly.
  2. A response that you don’t like is not the same thing as censorship. Too often online people like to log on, direct a rant at someone, and then back away with the last word. If the person being attacked so much as responds with a request for more respect or decorum, some people come back and demand that you stay quiet, because it’s their right to yell at you, without consequence or feedback. But that’s not how that the First Amendment works. If they get to speak their mind, so do you.
  3. No matter how hard you try to understand, you will always have a different version of reality than someone else. Someone else’s beliefs, reactions and points of view are shaped by their life experience, not yours. So what may make perfect sense to you may not make ANY sense to them. So rather than trying to get someone else to accept your version of reality as the only truth, try to find a space where you can hear each other’s points of view without judgement. It may not excuse or justify either party’s behavior, but it will definitely give you a better sense of where they’re coming from and help you find compassion and a way to connect
  4. Baiting is a real thing. Don’t buy into it. If someone @ replies you publicly over and over using harsh language and attempting to call you out (and call attention to themselves in return), you do not HAVE to respond. It’s a tactic as old as time and it’s the digital equivalent of sticking your foot out in a cafeteria waiting for someone to trip. Eventually someone will and then they’ll pounce. So if they’re baiting you over and over, block them or mute them and walk in the other direction.


Step 1: Listen. And then Listen Again.

I’m as guilty as anyone of forgetting to listen as much (if not way more) than I talk online. It’s easy to fall into a place where your words can be published at the blink of an eye and have a weight and life greater than themselves. But sometimes the most powerful thing you can do is listen. And listen again. Whether that means reading and re-reading a tweet or taking a break and walking away from an angry email before you re-read it again and then reply, that break to stop and think is crucial.

It’s so easy on social media to forget that there’s not a ticking clock behind us telling us we only have a minute to respond to someone. So if someone leaves a comment that upsets you and you want to whip off a response right away, consider taking a moment to step away, take a walk, or show it to someone else. In those moments I find a good deal of clarity and calmness can appear and help you phrase a response that doesn’t join in the argument, but rather side-steps it in favor of a more constructive conversation.

Step 2: Tell the other person that you hear them and tell them what you think they’re trying to say.

This is not a sarcastic tip. The simple act of saying, “I hear you. It sounds like you’re upset because…” and acknowledging someone else’s feelings is powerful and important. All people want to feel heard and understood and taking the time to do that, rather than “Oh yeah, well you’re a ….” can sometimes make all the difference.

The key here is to not make assumptions, like “I think what you’re trying to say is…” but instead just to summarize what they’re saying so you can start your discussion making sure you understand. So many times when I do this people say, “That’s not what I meant at all!” and I can avoid a meltdown and just get to the heart of what they DID mean and not have to get too worked up.

Once they confirm what they meant/said, ask them why they feel that way and what shaped that opinion. You may never expect what they’re about to say and it may change your opinions when you hear someone else’s reasoning. Always try to dig deeper if you can. I’ve heard stories and explanations for things that initially made me furious and then once I understand someone else’s side of the story, I feel calmer and have a deeper understanding of why they communicated the way they did.

Last but not least, acknowledge someone’s feelings and your role in them. You may feel that they’re overreacting or projecting, but, as my wise former-colleague, Max Tielman taught me, it doesn’t cost anything to acknowledge someone else’s feelings and express empathy for how they’re feeling. That’s a very different thing than apologizing or blaming. Rather than saying “Jane, I’m sorry I hurt your feelings, it’s all my fault” you can express, “Jane, I hear you. I’m so sorry that you’re feeling hurt. I know what that feels like and it’s awful. Thank you for telling me and sharing your thoughts here, I will keep them in mind.” It doesn’t guarantee an end to the discussion, but it’s a good step toward a more compassionate discussion.

Step 3: Once you’ve found compassion for the other person, have some for yourself, too.

I struggle with arguments sometimes because I focus too much on who “wins,” rather than trying to find a way to have a difficult discussion in which BOTH parties feel their feelings were heard and acknowledged. When that happens there may be no clear “resolution” (and that’s okay!), but if both parties walk away feeling like the other person heard them and understood them, that’s an important thing. It means the door of dialogue stays open (for the most part) and there’s room to come back to talk more another day.

So once you’ve found compassion for someone else and their point of view (step 2), be sure to respectfully communicate yours. It may be as simple as, “I hear you, but when you call me names, I feel defensive and attacked, and it feels difficult to want to continue a dialogue if I feel like you don’t respect me.”

Not everyone will come back with an apology or explanation, but if they can back away from the behavior that is disrespectful and hear that your feelings were hurt, too, they may be able to take a step back and re-approach from a more constructive place. And then you’ll be communicating from a place of BOTH parties feeling heard and understood. I’ve found that once parties feel heard, emotions die down significantly.

Step 4: Continue Dialogue + Find The Best Place to Continue

The verb dialogue means, “take part in a conversation or discussion to resolve a problem.” And while not all dialogue is easy, if the goal is to resolve a problem or find a sense of understanding, it’s something that can be done even between two total strangers in different parts of the world. So if you’ve both heard each other and are ready to keep digging deeper into your points of view, consider what the best place for that is. Maybe Instagram comments aren’t working and an email might be better. Or maybe a phone call if you know each other already. Take your conversation to the next level and, when possible, find a space where you can really have the space and time to listen and pay attention.

Step 5: Ending a Difficult Conversation 

Whether you end in agreement or disagreement (or something in between), there’s always the option to politely end the discussion. Some options I find helpful are:

Thank you for taking the time to talk with me, Jane. I know we don’t agree on XYZ, but I respect your opinion and for speaking up constructively here. 

Jane, I appreciate you taking the time to share your thoughts with me. At this point I hear you and feel I understand your point of view, but don’t have anything else to add to the conversation. I’m going to focus on new conversations, but my (online) door is open to new discussions in the future. 

There’s no reason that a conversation that starts with an insult or tough angle has to end with one. I have never once regretted not being “tougher” on someone online. But I have sure as heck regretted not ending one with more kindness and love. At the end of the day, ending on a compassionate note will always be a good idea.


Pitfalls to Avoid:

  1. Calling someone out publicly. If you want to make a point and you’re upset, try bringing this up with someone privately first. Whether that’s email or a private message or DM, this gives the person a chance to respond without feeling defensive because they’ve been put on the spot in front of their readers/clients/customers. If you accuse someone of something or ask them a controversial question in public, you shouldn’t expect them to not feel put on the spot — and that’s not the easiest place from which to start a constructive conversation.
  2. Using buzz words or names meant to insult. Whether it’s a catchphrase or a word you know will upset someone, avoid using terms that will shut people down. Whether you’re calling someone “basic” or a “snowflake,” know that using words with derogatory connotations will often immediately make someone feel defensive and show them you’re not interested in knowing them as a person and hearing their point of view. And if you’re not interested in hearing their point of view, don’t bring a discussion to their page.
  3. Give people a break (including yourself): You’re not always going to respond with kindness. Other people will do the same. Sometimes it’s ok just to say sorry and accept it wasn’t your best effort. And it’s ok to accept the same from others- and then move on. We’re all human and we all have bad days, so when you run into that feeling, just say the words and let it go. *I’ve written my share of emails over the years apologizing to people that just happened to catch me on a bad day or at a bad time. It’s a good idea to never be so proud that you can’t send a simple, sincere apology for not being at your best.

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  • Thank you Grace – there is a great deal of wisdom here. Being online has become a bit scary at times and I have been slowly withdrawing from places that feel unsafe to me. Intellectually, I know that strategic withdrawal can be a wonderful solution, however I am also deeply aware of how important it is in these troubling times to have a voice. Silence is assent. You have given me some very good reminders of how to be a good listener.

  • This is great! I have a friend who during the primaries was a Hillary supporter and our mutual friend supported Bernie. She would continually argue with him online and he was so gracious in his responses thanking her for keeping him and other supporters accountable (not trying to make this political, just a personal example). And he continued to just say things like “thanks for your feedback I hear you, this is what I’m seeing etc.”

    Anyway, I was attacked online by a family member when I posted a cheerful comment about my trip to the march in D.C. I didn’t know how to respond, and remembered my friend and how positive he always was. I realized my family member had made two comments about the economy and family. So I started my response telling him how great it was that we support the same things. It felt so good to respond in a positive way. AND he texted me an apology.

    Sometimes you have to remember to listen to the message and not the tone to really connect with people. Live with your palms wide open.

    On that note with dealing with difficult conversations, I recommend Lindy West’s interview with one of her trolls. It helps to remember we are all humans and sometimes attacks are out of fear.


    • whoa thanks for this lead…Lindy West is a BOSS and her story is unbelievable!

  • Timely post! I totally agree about the info-gathering approach vs. leading with judgement / info-giving.

    Asking “why do they feel this way” and approaching with curiosity — even, maybe especially, with viewpoints you find offensive — can really help de-escalate emotions on both sides, as it 1) gives them a chance to explain why they feel/think that way, 2) eases defenses since you’re treating them as a human and an equal, and 3) is more likely to lead to something productive and insightful than an inherently pointless comeback/insult/label.

    Imagine someone saying to you “I’m feeling really desperate to talk to you about this and understand your point of view, because I’m scared of ____.” , instead of the “You’re wrong, and this is why” approach. Understanding why people feel a certain way is absolutely vital when you’re wanting to effect change on either side.

    I needed a reminder to get back into this habit as well, thanks for this :)

  • Great post. Facebook became so overwhelming politically last week, that I am taking some time away. In just a few days, I already feel more at peace.

  • I very much appreciate this article. I haven’t had too many difficult conversations like this (thank Goodness), but the ones that I have had stick with me, painfully, for years. I feel there’s always room to improve in the way I react when feeling confronted and these tips are spot-on. I think we all need to read them and try to handle our online world with grace, class, and love for our fellow humans.

  • Dear Grace, in early January of this year I left a comment on one of your posts. It was written one day before my son’s surgery on his leg and I was in an emotional state as he has been treated badly by others because of his disability. My comment wasn’t malicious, but I questioned you as to why you mainly showcase female artists etc. I’m sorry if my comment caused you hurt. Also, I would like to thank you for your kind and thoughtful response back to me, in particular your suggestions regarding my son. Your response was compassionate and greatly appreciated. Wishing you a wonderful day from Australia.