What To Say When You Don’t Know What To Say: Navigating Challenging Conversations
Vitality Collective | Counselling Services for Individuals, Children, Youth, Couples, and Families in Vancouver, Surrey, Chilliwack, & Online
“Did she just say that?!”—We’ve all had this thought at a social gathering.
The holiday season often brings with it joyful reunions, warm traditions, and cherished moments. But for many, it also means navigating challenging dynamics in relationships—awkward questions, unexpected emotions, and moments when you’re left unsure how to respond. As an honourable mention, we all have that person in our lives who it’s mind-bendingly-hard to write a Christmas card for. IYKYK.
As clinic of counsellors with different specialties, we’re educated in psychology and trained to manage and guide conversations through emotional intelligence, effective communication, and even moments of reconciliation. We learn to become artful wordsmiths, finding ways to bridge discomfort and understanding.
Why Preparing Responses Matters
Having a mental “toolbox” of prepared responses can spare you those deer in the headlights moments and help you face difficult conversations with confidence and grace. Instead of freezing or feeling overwhelmed, you can calmly redirect the conversation or set boundaries, protecting your peace while maintaining the spirit of connection.
Tips for Navigating Awkward Conversations
Validate the Intent: Many uncomfortable comments stem from a place of love or curiosity. Acknowledging this can defuse tension.
Example: “I know you’re asking because you care—thank you for that.”
Set Boundaries with Kindness: If someone crosses a line, be firm but gentle.
Example: “I’d rather not talk about that right now, but I appreciate your understanding.”
Leverage Humor: Sometimes, a lighthearted response can shift the energy of the conversation.
Example: “Wow, you’re diving right into the deep questions! I might need a second helping of pie for that one.”
Have a Support System: Share a signal with a trusted family member or friend to step in or redirect the conversation if needed.
Here’s how you can do the same, with some real-life examples and ready-made phrases to help you navigate those tricky holiday interactions.
When Your Aunt Asks, “Is There a Special Someone in Your Life?”
Scenario: You’re content being single, are going through a breakup, or are still waiting for that special someone to show up and the last thing you want is to discuss your love life over turkey and mashed potatoes.
Light and Playful
"Oh, you know me—keeping things mysterious!"
"My love life is like a great novel… still being written."
"I’ll tell you when it’s Oscar-worthy!"
Polite and Redirecting
"Not much to share at the moment, but thanks for asking!"
"It’s private for now, but what’s new with you?"
"Oh, it’s a work in progress. How about you?"
Boundary-Setting
"I’d rather not get into it, but I appreciate your interest."
"That’s a topic for another day. Let’s talk about something else!"
"I’m keeping that under wraps for now, hope you don’t mind!"
Heart-Centered
"It’s something I’m holding close to my heart right now. Thanks for understanding."
"That question hits home. I’ll open up more when I’m ready."
"Love is complicated, and I’m still figuring it out."
When Someone Asks, “How Are You Doing?” (And You’re Struggling With Loss)
Scenario: You’ve recently lost a loved one, and it’s your first holiday without them. A well-meaning relative asks how you’re holding up, but the question feels heavy.
Light and Playful
"Oh, you know me—stubborn as ever, getting through it!"
"I’m here, I’m upright, and I haven’t burned the holiday dinner yet!"
"Surviving on love, memories, and way too much dessert!"
Polite and Redirecting Replies
"I’m doing okay, just taking it one moment at a time. How are you holding up?"
"Some moments are harder than others, but it’s nice to be here. How’s your holiday going?"
"I have my ups and downs, but being with family helps. How about you?"
Boundary-Setting Replies
"I appreciate you asking, but it’s a tender subject for me right now."
"Thanks for your concern—it’s still raw, and I’d rather focus on the present."
"It’s been hard, but I’d rather not get too deep into it today if that’s okay."
Heart-Centered
"I’m holding up as best as I can, but it’s been tough without [their name]."
"I’m managing, though their absence is definitely felt right now."
"It’s a hard adjustment, but being here with everyone helps."
When a Family Member Criticizes Your Life Choices
Scenario: A relative disapproves of your career, lifestyle, or parenting choices and isn’t shy about sharing their opinion.
Light and Playful
"I like to keep life a bit unpredictable, don’t you?"
"Well, it’s my adventure—could be boring if I followed the crowd!"
"I like to keep things interesting. Wouldn’t be me if I wasn’t doing something unexpected!"
Polite and Redirecting
"I appreciate you caring about my choices, but I’m really happy with the path I’m on."
"I hear you, but I feel good about where I am right now. How are you doing?"
"I know you have a different perspective, but I’ve found what works best for me."
Boundary-Setting
"I understand your concern, but I’d rather not discuss it. I’m confident in my choices."
“Thanks for sharing your perspective. I’ll keep it in mind, but this feels like the best choice for me.”
“Let’s agree to disagree on this one. I’m trusting myself with this one.”
Heart-Centered
"I know you want what’s best for me, and I do value your care. But this is what feels right for my journey."
"I know my choices may be hard for you to understand, but I’m making decisions that align with my heart."
"I understand your concern, and it means a lot to me. I’m just learning to trust my own path. We’re all different and I love that."
When a Sibling Brings Up Childhood Rivalries
Scenario: Your sibling starts recounting an embarrassing story from your youth—or brings up old tensions.
Light and Playful
"Ah yes, the good old days when I was your favourite target!"
"Oh, I remember that one. Classic me, right? I was ahead of my time in making memories!"
"Sure, bring up the embarrassing moments, but only if I can tell the real story about you!"
Polite and Redirecting
"That feels like a lifetime ago! Let’s talk about something we can laugh about now."
"I’ve moved on from that, but I’d love to hear what’s new with you."
"Haha, we were kids! Let’s focus on the present—how’s everything going with you?"
Boundary-Setting
"I’d rather not revisit that story—it doesn’t really feel good to talk about anymore."
"That’s in the past, and I’d prefer to leave it there. Let’s talk about something else."
"I know you’re joking, but I’d rather not get into old family tensions today."
Heart-Centered
"I get it, we had our moments growing up. But I’d love to focus on the bond we share now."
"I know those moments are a part of our history, but I’m really working on leaving the past where it belongs."
"I appreciate the memories, but I feel like I’ve grown since then. Let’s focus on how we’re both doing now."
When Someone Makes a Comment About Your Appearance
Scenario: A relative remarks on your weight, hair, or outfit in a way that feels judgmental or invasive.
Light and Playful
"Well, I guess I’m just embracing my fabulous self today!"
"I’ve been experimenting with new looks—what do you think, trendsetter or not?"
"Oh, you noticed! I was going for ‘mysterious chic’—maybe I nailed it, maybe not!"
Polite and Redirecting
"I’m feeling good about how I look today, thanks for noticing. How have you been?"
"I’ve learned to love my body as it is—let’s focus on what’s going on in your world."
"I’m just enjoying what feels right for me, but I’d love to hear more about you!"
Boundary-Setting
"I prefer not to talk about my appearance—it’s personal to me."
"Interesting perspective, but I’m comfortable with how I am right now."
"That’s not something I’m open to discussing, but I’m glad you care."
Heart-Centered
“Thanks for noticing! I’ve been focusing more on how I feel rather than how I look, and I’m loving it.”
"I’ve worked hard to feel comfortable in my own skin, and I hope that shows."
"I understand where you’re coming from, but I feel happiest when I focus on what makes me feel whole, not just how I look."
When Political or Controversial Topics Arise
Scenario: A heated political debate starts at the dinner table, and you’re uncomfortable or don’t want to engage.
Light and Playful
“The holidays are my time to unplug from the news—let’s keep it light today!”
"I’m just here for the mashed potatoes, not the debates!"
"Can we table this for another time? I’ve got a full plate already—literally and figuratively!"
Polite and Redirecting
"I’m not really up for a political discussion tonight. How about we talk about something lighter?"
“I’d rather focus on what brings us together instead of what divides us. Who’s up for charades?”
"I’m not super comfortable diving into politics, but I’m happy to chat about other things. What’s new with you?"
Boundary-Setting
"I’d rather not engage in political debates, especially during family time."
"I understand that this is important to you, but I’m not willing to discuss it right now."
“I think we all have strong opinions here. Let’s agree to enjoy the meal instead.”
Heart-Centered
"I know this is a topic that matters to many, but I’m not comfortable discussing it in this setting."
"I believe in respectful dialogue, but I don’t feel it’s the right moment for a big debate."
"I understand that these topics are important, but I’ve chosen not to engage in these discussions for my own peace of mind."
When Writing a Christmas Card Feels Awkward
Scenario: There’s that one person on your holiday card list—perhaps an estranged relative, a colleague you barely know, or a friend with whom things have grown distant. You’re not sure what to say, but you want to acknowledge them without it feeling forced or awkward.
Tips for Crafting a Thoughtful Yet Neutral Message:
Keep It Simple: Stick to generic but warm sentiments that reflect the spirit of the season.
Example: “Wishing you and your family a joyful holiday season and a bright new year ahead.”
Acknowledge Shared History: If appropriate, reference positive memories without delving into unresolved issues.
Example: “I was thinking about the fun we had at [insert shared experience]. Hoping your holidays are filled with warmth and happiness.”
Focus on Positivity: Even if the relationship feels strained, a kind tone can open the door for better communication in the future.
Example: “Sending you warm wishes for a peaceful holiday season. May the new year bring you health and happiness.”
Express Gratitude (if applicable): If the person has had a positive impact on your life, acknowledge it.
Example: “Thank you for the role you’ve played in my life. Wishing you a wonderful holiday season!”
Sign Off Graciously: Close with a signature that matches your level of closeness and comfort.
Options: Warm regards, With appreciation, Sincerely, or Wishing you all the best.
By focusing on kindness and neutrality, you can navigate even the trickiest holiday card situations without stress—and who knows, it may even start paving the way for a better relationship next year.
When in Doubt, Pivot with Gratitude
If you’re truly at a loss for words, gratitude can be a powerful fallback.
“I’m just grateful we can all be here together this year.”
“It’s been a challenging time, but I’m so thankful for moments like this.”
Navigating tricky conversations isn’t always easy, but with a little preparation and self-compassion, you can handle even the most uncomfortable dynamics with grace. And if you need additional support or want to strengthen your communication skills, registered clinical counsellors can help. Our expertise in emotional intelligence, relational issues, and conflict resolution is designed to help you build stronger, more meaningful connections.
This holiday season, prioritize your peace—and don’t be afraid to lean on the tools that help you protect it.
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