10 Conversation Starters to Connect With Your Young Adult Child This Holiday

I remember the days when my kids were away at college. I couldn’t wait for the holiday breaks that brought them home. The house felt alive again. These days, I find myself packing a bag and heading their way, eager for any chance to share a meal or catch a moment. I've always been a quality time girl, and I think that's one of the hardest parts of parenting young adults—not being part of their everyday lives anymore.

When we finally do get time together, the days go fast. Between friend plans, naps, and travel logistics, the window for real connection can close quickly. If you’re not intentional, it’s easy to get caught in the surface-level catch-ups and miss a beautiful opportunity to go deeper.

So whether your adult child is coming home for the holidays or still living under your roof, these conversation starters can open the door to meaningful connection. No pressure. No lectures. Just curiosity, love, and the chance to learn something new about the person your child is becoming.

10 Conversation Starters to Try This Thanksgiving:

1. What’s something that surprised you about this past semester/year?

2. What’s one thing you're proud of that most people wouldn’t know?

3. Has anything shifted in what you want for your future lately?

4. What does a really good day look like for you right now?

5. Is there anything I used to do that you miss (even if it annoyed you at the time)?

6. What kind of support feels most helpful to you these days?

7. What’s a recent moment that made you laugh hard or feel really alive?

8. What’s one thing you’re learning about yourself this year?

9. What’s something you wish people understood better about being your age right now?

10. What are you grateful for right now that you might not have noticed a few years ago?

You don’t need to ask all ten. Just pick one and see where it leads. Sometimes one thoughtful question can unlock a whole new layer of understanding between you.

Connection in midlife takes intention. And parenting adult children? It’s a whole new dance. But don’t underestimate the power of simply showing up with love and curiosity.

Looking for more tips on navigating the holidays in midlife? Sign up for the Midlife With Purpose Newsletter or check out the Launching With Love course designed to help moms build connected, confident relationships with their young adult kids.

💗 You don’t have to figure this season out alone.