Conversations With Family...at the Thanksgiving Table

You can nearly smell the pumpkin pie and sage stuffing as we enter November. Moments of gratitude start to pop up, and the warmth of the Thanksgiving holiday begins to consume our thoughts. Thanksgiving is a time for gathering, reflection, and connection. And while dreams of the legendary day-after turkey sandwich start dancing in your head, thoughts are more complicated as the holiday approaches for the Sandwich Generation – you know, those adults caring for their own children and also their aging parents.

As Thanksgiving looms for the Sandwich Generation, many of us find ourselves not just celebrating with our families, but also navigating the complexities of change for aging parents. This Thanksgiving, consider using the occasion to have meaningful conversations with your parents. Here are some topics and tips to guide your discussions, making the most of this special time together. Find a few that seem appropriate for your family dynamics and remember these three rules for the road: be respectful, be curious, be empathetic.

Cherished Memories

This one’s your softball. Get the juices flowing and find the common thread of joyful memories with family. Start by reminiscing about past Thanksgivings and family traditions. Ask your parents to share their favorite memories from your childhood or their own upbringing. This not only opens the door to delightful storytelling but also helps you appreciate the legacy of your family’s history.

Tip: Bring along some old family photos to spark memories and encourage storytelling.

Set the Stage: “I’m so excited to see you at Thanksgiving! One of my favorite traditions is our game of charades after dinner – let’s remember to get a photo this year! And speaking of photos, I’m picking out a few photos from our childhood to share over brunch Friday – please bring some, too!”


Family Traditions and Legacies

Talk about the traditions that mean the most to your parents. Encourage them to share the significance behind family recipes or rituals and discuss how you can continue these traditions with the next generation.

Tip: Suggest creating a family recipe book or video recording their stories to preserve their legacy for future generations.

Set the Stage: “I love that we always have Grandma’s dressing at dinner. What’s your first memory, Mom, of eating it? Have you ever wanted to change it? What are some other recipes you remember – good or bad – from growing up?”

Health and Well-Being

Once you have the juices flowing, it could be a suitable time to bring up health. While it might feel uncomfortable, discussing health is essential. Approach this topic softly and gently by asking how they’ve been feeling lately or even by referencing how their friend’s health is and how they’re feeling about it. Share any concerns you may have about their health or mobility and encourage them to talk about any changes they’ve noticed.

Tip: Remember to be respectful and notice body language cues on their end. Try to use “I” statements to express your feelings, like “I worry about you sometimes, and I want to make sure you’re okay.”

Set the Stage: “Hey Dad, you mentioned how your friend Joe had a stroke earlier this year. That’s got to be so hard – and sudden. If I think about it, I feel really scared to think about that happening to you. Do you feel scared about that? What comes to mind when you think about your own health right now?”

Future Plans

Ready for the big one? Engage your parents in conversations about their plans for the future. Remember that discussing their living situation, healthcare preferences, and any potential need for assistance can be quite sensitive, so it’s important to bring some grace and empathy to the conversation. This is an opportunity to understand their wishes and involve them in decision-making.

Tip: Frame the conversation positively by focusing on what they enjoy most about their current lifestyle and how you can support them.

Set the Stage: (For big and often sensitive topics like this, I like to give a heads up.) Some of my friends are having to navigate tricky decisions with their parents who are a bit older regarding where and how they live. “I was wondering, Mom and Dad, if you’d be open to sharing some of your current thoughts on your own lifestyle and wishes? I’d really love to hear what comes to mind for you; let’s talk more when I’m home for Thanksgiving.”

As you gather around the Thanksgiving table this year, remember that these conversations with your aging parents can be both heartwarming and necessary. And remember to be reasonable about your goals for the conversation. If this is your first time ever talking about things with your parents, start by just trying to create some shared connections over memories and legacy and cultivating a space for open dialogue. You can build from there. You will not only strengthen your bond but also create a supportive environment for your family. Embrace these moments—they are the threads that weave the fabric of family history and connection. Happy Thanksgiving—and let me know how it goes!



SEE ALSO: Lifestyle Creep: The Sneaky Saboteur of Your Savings


This communication is for informational and educational purposes only. No content or reference is intended to be a recommendation for the sale or investment in any product, strategy or service nor should it be perceived as individual advice. Please seek the advice of a financial advisor regarding your particular financial situation. Visit xmlfg.com for more information. 

Lauren O’Brien, CFP®, RICP®, CPA

Lauren serves as Senior Wealth Advisor at XML Financial Group and maintains the credentials of CERTIFIED FINANCIAL PLANNER™ professional and Retired Income Certified Professional®. She’s on a mission to make money more conversational and empower women to financial success. 

She was raised in Northern Virginia before obtaining her business degree from the University of Notre Dame. Following stints in Chicago and London, she returned to the DMV and happily settled in Old Town. 

You can find her at home cooking a new recipe, at a wine tasting in town, or delving into an Excel spreadsheet. She is an avid traveler and recently completed her quest to visit all 50 states.

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