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“It’s the Most Wonderful Time of the Year” for Difficult Conversations!

Is the mere thought of the holidays and all those fun family gatherings filling you with cheer… or fear? 
Filled with fun winter activities, yummy treats, and brightly wrapped packages, it’s no wonder so many people love the holiday season. However, it can also be a time of stress, loneliness, grief, and anxiety. When families and friends gather together for the holidays, it’s always a possibility that negative feelings and difficult conversations will be stirred up with the turkey gravy.  If your family isn’t the cloned perfection of a 1950s magazine advertisement, the holidays can be an emotional struggle. 

Peruse the list of recommended holiday movies on any streaming service, and you’ll notice the most common storyline revolves around family drama. Other than the “enemies to lovers but one of them is a paid Santa assassin and Santa just so happens to be the other one’s father” cinematic masterpiece, toxic families dominate the plot of most holiday films. Families have a unique ability to pluck at our most vulnerable heartstrings and exhume the most humiliating moments of our lives: Moments that should stay buried. 

The combination of “harmless” family teasing and other emotional triggers shake up a toxic cocktail of tension: Throw in the large quantity of actual cocktails consumed at these holiday gatherings (along with the sore losers at board games – ahem, my father flipping the Monopoly board year after year), and the result could be more explosive than a high school chemistry lab.

Everyone Telling You to “Be of Good Cheer!'”

Holiday dinners don’t have to be miserable, and you shouldn’t feel the need to control your internal boiling for an entire holiday just to avoid conflict. You can express your negative feelings and set those necessary boundaries without setting yourself up to be the Scrooge of the family. Just another harmless memory to tease you about: “Remember that holiday when you exploded at us during dessert because you hate the holidays and hate your family?”
That family hilarity makes you want to plunge a stake of holly through your heart year after year, doesn’t it?

Laughs and little jabs at your expense should not be part of the holiday tradition if you can prevent them. However, you do need to be willing to risk a moment of discomfort – and potential conflict – to talk about how you feel before exploding years of anger all over everyone. These difficult conversations can be productive and respectful, but they should be handled with dignity and a mature mindset. Aside from this, you also have to be honest with yourself about whether you can handle the emotional weight of this conversation without losing your mind.

So what’s the key to having a difficult conversation with family and friends without sacrificing your sanity or ruining everyone’s holiday?

But First, Priorities

People often celebrate the holidays from a perspective of obligation and tradition without prioritizing their own priorities. Oh, the irony. 

You should ask yourself: What drives your decisions about holiday plans? Who do you spend your holidays with and how far are you expected to travel for them? 

What are your priorities? What are you unwilling to compromise on? When you are in a conversation with someone who has a different perspective, do you feel your priorities are compromised for the sake of winning an argument?

One way to maintain your mental health and those family relationships is to know what your priorities are so you are able to have a conversation without feeling attacked. Whatever the priority is, communicate it with confidence: You know your reasons and you don’t have to explain yourself. Even if you are questioned or criticized, you can approach these criticisms with confidence in your reasons. 

If you prioritize according to your physical and emotional needs, you will be operating as your best self and can shift attention to more serious situations without crumbling under holiday pressure.

Determine Your Boundaries Before Entering the Lion’s Den

Two lionesses lie with cubs looking right

Certain topics, such as politics and religion, have not been discussed openly enough for us to see that uncomfortable disagreements can be discussed productively. As a society, we rarely witness a disagreement that doesn’t turn ugly: On social media especially, differences in opinion often devolve into negative assumptions of character and personal attacks. Many of us were told not to discuss negative feelings and other unpleasant topics. We were taught to avoid conflict and keep the peace. Now we don’t know how to have these uncomfortable conversations without all the negative emotions and character assassinations. 

Sometimes, these conversations are necessary to show you love someone enough to openly express your feelings and move the relationship forward: Other times, it’s not the right time. Or the right place – or the right situation. How do you know when to speak and when to stay silent? 

One of the first things you need to do is to know what your perspective is and why. Ask yourself if you’re open to having this conversation and if you’re willing to listen to another point of view. This isn’t a university lecture hall: A conversation doesn’t just involve spewing your thoughts all over a person and expecting them to stay silent.

Know your own emotional boundaries and whether you are truly prepared to hear the other side of things, which might involve a discussion of your actions.  Is the other person ready for this conversation, or are they lacking the emotional space to process it? Can you express your feelings calmly and rationally without attacking their character? If not, that is a clear boundary you should not cross until you know you can do so respectfully. 

Being aware of these boundaries and clear in your perspective can help navigate the conversation while protecting the other person’s feelings.

 5 Tips for Having Difficult Conversations Hand drawn sketch on chalkboard of two people arguing with each other instead of using active listening strategies

  • Know when to speak and when to wait. Emotional urgency tricks you into believing that certain conversations have an expiration date: Reenee Singh, a family therapist of the Association for Family Therapy and Systemic Practice (AFP), believes “Silence can be protective and even help relationships sometimes…talk later, when the situation has lost its emotional urgency. Some conversations need to take place in a reflective spirit.” [1]Is this holiday setting the best place to have this conversation? Is it one that should wait for another time? No one is going to listen to anything you have to say if you’re yelling in the eye of the emotional storm. Maybe schedule a coffee chat or a walk after the holidays are over to work through perspectives at a safe distance from the initial emotional reaction.
  • Some social clichés are still true: For arguments circling the drain, just agree to disagree: Sometimes you’ll be able to reach an agreement, but other times you may have to end the disagreement without a resolution. You don’t have to sacrifice your position. Although, you may need to let the other person continue vocalizing their own perspective. You may never reach a point in the discussion that will resolve everything: You have to be comfortable with that possibility, and ensure the other person understands your reasons for doing so as well. 
  • Active listening is just as important as speaking your own truth:
    Being heard and validated is very powerful. A productive conversation is not a Geology 101 lecture with 300 students and one monotone professor reading from a PowerPoint.  The other person shouldn’t sit silently while you go on and on about your feelings and beliefs: After all, taking turns is not just for Kindergarteners!
    1 – Nonverbal Signs of Active Listening: Show them you’re listening by nodding your head and making eye contact (but not direct eye contact for TOO long, because this creates a creepy discomfort that triggers our fight-or-flight response)
    2 – Acknowledge their words with validating sounds/phrases, such as: “Mmhmm,” “Okay,” “That’s understandable/reasonable,” “I get that,” “That makes sense,” or “I see your point.”
    3 – Be careful of your tone and body language when using these sounds of acknowledgement: Using a sarcastic tone of voice and a standoffish posture – crossed arms, tapping your feet, and/or tightening your jaw -will not show the person that you are listening to them, or that you respect what they have to say.  
  • Avoid playing the blame game: Focus on “I feel” statements rather than “You did this to me” statements.
    No one wants to be accused of intentionally hurting someone they love, and these blaming statements only stir the pot of negative emotions and trigger the self-defense response. By putting the responsibility for your feelings back on yourself, you can show the other person that you own those feelings. It doesn’t matter what their intentions were when you felt them.  You own them. Taking responsibility for what you feel – instead of making it seem like the other person wanted to hurt you – builds understanding and strengthens the emotional connection.
  • Focus on the facts that support your perspective: Don’t give in to your emotional reactions to rising tension. When these conversations devolve into heated arguments, it’s helpful to separate the discussion of facts from your expression of emotions arising in the moment. When tensions are high, avoid escalating the conflict by forcing yourself to stick to the facts only.

Later, reflect on the emotional impact of the disagreement , how you responded, and your emotional triggers. Taking time to reflect on your feelings separately from the heat of the moment could give you helpful insights that allow you to grow. During the conversation, focus on facts first and feelings second to promote productive dialogue without any personal attacks.

Don’t be afraid of difficult conversations: Getting through them together will strengthen your bond

A group of adults walking in the rain at night bonding together and getting through the hard times by being there for each other

No relationship or friendship is perfect: Be who you truly are while still respecting the other person for who they truly are. Show yourself some grace if the conversation completely falls apart, because not all difficult conversations are resolved in the moment. Remember to have empathy for the other person, and make sure they know you still care about them afterwards. When you know your boundaries and respect the other person’s emotions and perspectives, you’ll have a much more productive discussion and possibly save the relationship.

These difficult conversations might feel like being boiled in your own pudding at the time, but the emotional connections will be so much stronger going forward.

In fact, getting these conversations out of the way with love and respect for the other person will help you enjoy your holiday gatherings even more: You might even get through one holiday without being compared to Scrooge at all, because you’re just that sickeningly pleasant. Humbug.

Originally posted December 7, 2022. Updated December 22, 2023


  1. How to Have a Difficult Conversation | Psychologies UK | Association for Family Therapy and Systemic Practice UK


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Disclaimer: This content is for educational purposes only. It’s not intended as a substitute for the advice provided by your Wellness Way clinic or personal physician, especially if currently taking prescription or over-the-counter medications. Pregnant women, in particular, should seek the advice of a physician before trying any herb or supplement listed on this website. Always speak with your individual clinic before adding any medication, herb, or nutritional supplement to your health protocol. Information and statements regarding dietary supplements have not been evaluated by the FDA and are not intended to diagnose, treat, cure, or prevent any disease.

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