The Reconnect Deck – 35 Questions to Ask Your Parents | Dr. Jenny Shields

The Reconnect Deck.

35 therapist-designed prompts that turn small talk into healing conversations between adult children and their parents.

Start Your First Conversation →
TIME Magazine logo

Featured in TIME Magazine: Dr. Jenny Shields recently collaborated with TIME senior health editor Angela Haupt on a piece about the meaningful conversations we often avoid, yet deeply need to have. Dr. Shields offers guidance on 10 essential questions—questions that align beautifully with the spirit of the Reconnect Deck, designed precisely to help people navigate complex conversations with clarity, compassion, and courage.

Read the full TIME article →

Most of us think we have more time—time to ask the big questions, untangle old knots, or finally speak truths we've held back for years. Regret hits hardest when we realize the time we counted on might never arrive.

We stall because meaningful conversations can feel risky. But missing these moments means losing priceless connections. Imagine deeply knowing your parents—not just their choices but the dreams and fears behind them.

Even when we find the courage, conversations stall in predictable ways:

“Every time I try, Mom launches into a when I was your age… story.”
“Dad doesn’t want to ‘bother’ me, so we text NFL memes instead of feelings.”

Why it feels awkward

  1. Outdated roles: You're adults now—but still trapped at the kids’ table.
  2. Land-mine fear: Family histories hide emotional triggers; we tread carefully.
  3. Different life scripts: You change jobs yearly; your parents collected stability like trophies.

Structured prompts make it easier. They guide you through four approachable stages.

Gentle StartersOrigin StoriesGenerational ShiftForward Pact

Stage overview

StageWhy it worksSample prompt
1 · Gentle StartersCreates comfort, reduces anxiety“Which song have you had on repeat lately?”
2 · Origin StoriesBuilds empathy, heals old wounds“What feelings weren’t allowed when you were a kid?”
3 · Generational ShiftBreaks patterns, fosters adult-to-adult talk“What cycle are you consciously breaking?”
4 · Forward PactCreates rituals, sustains connection“What small tradition would you love to start?”

Rules to Remember

Lead with warmth

Curiosity, not critique. Listen like a friend.

Shrink the ask

One meaningful question beats ten shallow ones.

Flag the novelty

Own the awkwardness—explain why you’re digging deeper.

Pair with comfort

Wrap the chat in comfort: coffee, snacks, familiar spot.

Promise an exit ramp

Freedom matters—make it OK to pass on any question.

End on a ritual

Anchor the moment in something memorable.

Ready for conversations worth remembering? The Reconnect Deck handles the awkward part—just choose a stage, ask the question, and listen like your future depends on it.

The Reconnect Deck

How to get started:

  • Choose a stage: Gentle Starters, Origin Stories, Generational Shift or Forward Pact.
  • Select 1–2 prompts: Tick the boxes next to the questions you love.
  • Print: “Print selected” for just those, or “Print deck” for all 35.
  • Bring it with you: Take your sheet to your next chat and listen.
  • Stage 1 of 4: Gentle Starters

    Gentle Starters
    Get Curious
    A Little Deeper

    Tap a prompt → ask → listen. Two solid questions = victory.

    The Reconnect Deck” by Dr. Jenny Shields is licensed under CC BY-NC 4.0 . Feel free to share it non-commercially, with attribution.

    Portrait of Dr. Jenny Shields

    Dr. Jenny Shields

    Licensed clinical psychologist & conversation designer helping adults turn small talk into healing talk—at home, work, and everywhere in between.

    Dr. Jenny Shields dancing with her father Todd E. Daer

    IN LOVING MEMORY · The Reconnect Deck

    Todd E. Daer.

    For the man who gave me the super-power of listening deeply enough to let my mind change —and taught me to love recklessly enough to help others change theirs.

    Find More Helpful Tools →