personal growth

Written By: DiveThru Team

Reviewed By: Amanda Kobly M.Ed., Registered Provisional Psychologist


How to Have Difficult Conversations with Your Loved Ones

PUBLISHED Aug 17th, 2022 & UPDATED ON Feb 23rd, 2023

It’s tough to disagree with loved ones. Really tough. Ideally, we could just avoid fighting with our families, friends, and partners… but it’s not an ideal world, is it? It’s important to know how to have difficult conversations so that you can navigate small and major disagreements when they happen. 

Whether it’s small things like putting away laundry to bigger topics like finances or family planning, there are some overarching tips to help mitigate awkwardness or anger. Let’s dive thru some ways you can manage difficult conversations with loved ones: 

1. Prepare 

Think carefully about what you want out of the conversation. If it’s an argument, ask yourself what a reasonable resolution would be. If it’s a discussion about planning for the future, ask yourself what compromises you’re willing to make. When preparing, be mindful that the discussion should only be about one topic—if you have other grievances or concerns, try to keep those in a separate conversation, and don’t bring up old disagreements. Prepare to “fight fair,” because yelling, insults, and silent treatment don’t create anything positive. 

It’s also a good time to remind yourself why this person is important to you, and that they’re most likely not your enemy. Just because you have a different perspective or opinion, does NOT mean that you still don’t love them and value their presence in your life. Obviously, there are some things that are not okay to ignore in the name of family or love, like racism/ sexism/ homophobia or abuse. Those are more challenging convos and we’ll tackle them later in the article! But for other disagreements, remember that your endgame is not to “win” the argument at all costs, but to come to an agreement. 

2. Choose a Time 

While it might be tempting to blurt out your frustrations in the heat of the moment, that’s not the best way to handle sensitive subjects. Pick a time when both of you are free, but not right after work or before bed. Also, maaaybe don’t shoot them a “we need to talk” text because that’s a day-ruiner right there. 


3. Phrasing 

Because we all have a tendency to feel personally attacked when having arguments or serious discussions, it’s a good idea to phrase things in a non-accusatory way. Even though you may be feeling upset, people are more likely to get their guard up if they feel like they’re being accused of something. Here’s an example: 

Poor phrasing: “Can you not be so lazy and clean up after yourself? I’m sick of always putting your dishes away.”

Better phrasing: “I feel stressed when our house is messy. Can you help me keep things tidier?”

In the latter example, the person says how they’re feeling, doesn’t ascribe blame, and asks for a resolution they can work together toward. 

In another example, where a relative says something offensive at a family gathering, flat-out saying “you’re being shitty” isn’t going to foster a conversation. If you have the bandwidth for it, framing the conversation as being helpful is more likely to create a dialogue (calling someone in, instead of out).

Something like “hey [name], that’s not the best way to say that. Here’s what you should say next time. I know you’re not a bad person so I’d hate for you to make other people feel unsafe unintentionally.” 

Obviously it’s a different conversation entirely if it’s not the first time and someone is intentionally being, well, shitty. But if a loved one uses a wrong or dated term, and you feel you can put in the emotional labour to talk about it, calling them in instead of calling them out will go a long way. 

4. Listen 

An important thing to remember when having a difficult conversation is to listen. You might be hopped up on adrenaline and anxiety, but allowing your loved one space to express their feelings and be heard is really important. Instead of catching your breath and waiting for a pause so you can start arguing your side again, listen to what they’re saying. Work to understand why they feel or act the way they do, instead of ascribing intent. 

If your goal is to work together with your loved one to find a solution, that can only truly be done by understanding where each of you is coming from. As far as how to have difficult conversations where one of you is clearly in the wrong, that’s another story and we’ll dig into that more later. 

5. Acknowledge Your Bias and Assumptions 

Everybody is the main character in their own story. And while you might try your best to be open and understanding with others, you will always have a bias because you can only ever truly know your own POV. So, acknowledge that. Understand that your truth isn’t necessarily the objective truth. 

Likewise, as tempting as it may be to try to plan out exactly what your loved one is going to say before a discussion, you’re making assumptions about their feelings and perspective. Going back to that example argument about cleaning the house, it can be tempting for the one person to assume their partner is just being lazy, but that’s still an assumption. There are other possibilities, so listen to them (hey that was tip #4!). Work to understand their perspective without judgment, because that’s what you want them to do too! 

6. You Don’t Have to Win Every Discussion  

Most of the time, even difficult conversations with loved ones aren’t a zero sum game. Conversations about household chores, planning for the future, or even beliefs do not need to have a winner and loser. 

If you view every interaction with a loved one through the lens of a scorecard, you might “win” an argument but at a great cost, where ultimately the toll it takes isn’t worth it. Consider how you would feel if your partner fist-pumped and whooped after a difficult conversation… the relationship would suffer. Even in major disagreements, the goal should be to move the relationship forward, and that means everyone wins—even when they have to compromise. 

7. Deal in Good Faith 

The previous three points really could be summed up as discussing in good faith. We don’t mean religious faith—we’re talking about the legal term. If you’ve seen enough of Suits or The Good Wife, you know that good faith is the sincere intention to deal fairly with others. So basically go into the conversation with good intentions toward creating the best possible result for everyone involved. Sometimes that might mean you’re “right,” but remember that’s not the point. Just be the kind and amazing person that you are, and your loved ones will be inspired to be kind too! 

3 Types of Difficult Conversations 

Let’s get technical! There are many levels of tough conversations, from day-to-day arguments to big-picture disagreements. While the severity of topics and consequences vary, they’re all stressful to handle in their own special ways. Let’s dive in! 

Day-to-Day Arguments 

These can be run-of-the-mill arguments, like household chores, staying out past curfew, or the result of a poorly-phrased comment. When dealing with these, it may not require as much planning or scheduling, but there should be an emphasis on phrasing and listening. So think constructive criticism instead of yelling.

This can also include setting boundaries with your loved ones. Which can be really hard! You might feel guilty, anxious, full of self-doubt, and a whole bunch of other stressful emotions. But there’s a reason that you want to set the boundary, and in these cases the only emotions that are relevant are yours. When setting a boundary, phrasing is important. You’re ultimately telling someone what you want and what the consequences are if that boundary is crossed. 

“If you make comments about my appearance then I’m going to leave.” 

“If you don’t stop yelling at me then I’m going to hang up the phone.”

While phrasing is important, you ultimately can’t control their response. Some people have a hard time being told no and will take it v personally. That’s why phrasing the consequence as something you will do is better than saying they won’t be allowed to do something. It’s up to them how they respond, but phrasing boundaries clearly helps remove any loopholes or misunderstandings they might try to find. 

Planning for the Future 

It can be awkward to plan your future with your partner. Sure, odds are you’re already pretty open with each other about what you want in life, but it’s still uncomfortable to put yourself out there. Figuring out plans for where you want to live, if you want to marry, whether or not you want kids (or how many!), how you’ll split costs, and other big life choices is STRESSFUL. 

For these conversations, all of the above tips are relevant. Don’t spring a conversation about opening a joint bank account on your partner over lunch. Set a time and give both of you a chance to prepare. Be mindful of phrasing, because there’s a big difference between “I don’t think we need a joint account because xyz” and “I don’t want you spending MY money.” 

And speaking of family planning, if you do decide to be child-free, that can be a very difficult conversation with your families. Once again, plan ahead when and how you’re going to tell your loved ones, and set clear boundaries about future discussions. You can only control how you tell people something, not how they feel about it.  


You’ve probably heard something to the effect of “never discuss religion or politics at the dinner table.” There’s a good reason why! 

Our brains are hardwired to reject information that contradicts our beliefs. If you haven’t seen it before, check out this great comic on the backfire effect. As the author put it, making snap judgements based on emotion over logic makes sense from an evolutionary perspective because “if you were a caveman and another caveman threw a boulder at your head, you wouldn’t react by logically debating the pros and cons of getting brained.” BUT unfortunately this also means that we’re far more likely to fall victim to confirmation bias, where we only look for information that supports our view instead of looking for objective evidence. 

This makes conversations about politics, religion, and other beliefs much more difficult. Not everybody has the same beliefs, and that’s okay. If you disagree with someone about iPhone vs Android, or Marvel vs DC, that’s totes fine! But if someone’s beliefs preclude them from believing that all humans should have equal rights, then that’s NOT okay. 

How to Handle These 3 Types of Difficult Conversations

So, what the heck are you supposed to do if your loved ones are sharing conspiracy theories about the pandemic or making thinly-disguised (or blatantly) racist comments? How do you have that particular difficult conversation without things getting awkward or defensive? 

1. Start With Your Boundary

Think of it like setting a boundary. As mentioned above, the best way to set boundaries is to explain how you feel. 

“If someone is choosing not to be vaccinated then I don’t feel safe having them over for dinner, regardless of whether we’re related.” 

“If you continue calling the pandemic a hoax then I’m going to stop coming over to visit you.”

“When I hear you talk like that about women’s reproductive health, it makes me feel uncomfortable. I don’t want to feel that way around my family.”

If the person gets angry, then you can choose to end the conversation and enforce your boundary. At that point, you need to do what’s best for your own mental health, and hope your loved one figures it out on their own. Australian journalist Myke Bartlett had this comparison for people dealing with major disagreements with loved ones: 

“This is a lesson most parents learn eventually. You can tell your kid there’s no monster under the bed, but you can’t stop them feeling like there is. All you can do is turn on the light, let them do the work and hope they eventually come to the right conclusion.”

2. Work Through the Awkwardness

If someone is open to having a good faith conversation, then you can choose to continue (or plan a future time to talk). It’s probably going to be awkward, but you know what they say about breaking eggs to make an omelet. Ijeoma Oluo, author of So You Want To Talk About Race, had this to say about working through that awkwardness: 

“Know what your goal is, and state that goal, and then tailor the conversation towards that. If you come in really confrontational … and your goal is to get them to be more supportive of you, that’s not going to achieve the goal. If you want them to know that maybe the things they’ve been saying are unacceptable, then maybe just saying, ‘You know, this is unacceptable, and this is why,’ is your goal.”

3. Listen to Their Fears

Listening to your loved one’s concerns can also help foster a conversation. Fear is a powerful motivator and can overwhelm logical thinking. Listening to your loved one talk about their fears, even if unfounded, will make them feel validated. You’re not actually validating their problematic belief, just the fact that they feel scared—but that can be enough. People may feel attacked if they feel they are being criticized for a belief they honestly hold. Oluo again, on listening: 

“[I recognized] that the fear I was hearing … was fear that maybe this was going to divide us …. So me being really clear about how I needed her to support me … gave her a purpose and a place.”

Of course, this is all related to good faith conversations. If your loved one seemed open to chat but then refused to acknowledge their bias, used false evidence without remorse, or became hostile, then the only thing you can do is enforce your boundary. It sucks, because you never want to feel like you need to choose between your own mental health and a loved one. Just remember, all you can control is your words and actions, not your loved ones response. 

We hope this helps you deal with major disagreements or difficult conversations with your loved ones. But either way, we’re proud of you for being thoughtful about how you handle whatever situation you find yourself in. 


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