Most of us believe we know the people we care about. We know their jobs, their routines, their roles in our lives. But how often do we slow down long enough to ask the questions that reveal who they really are—their memories, values, fears, joys, and hopes?

That’s exactly what the Have the Talk of a Lifetime Conversation Cards are designed to do.
Recently on the Remembering A Life podcast, I had the opportunity to sit down with my colleague and friend, Skip Weiss, and use the cards exactly as they were intended: pulling questions at random and answering them honestly, without an agenda, and without rushing to the next thing. What unfolded was a deeply meaningful conversation—one that reminded both of us why these questions matter so much.

More Than Small Talk

The Have the Talk of a Lifetime Conversation Cards include 50 thoughtfully written questions that invite reflection and connection. These aren’t icebreakers or party games. They’re prompts that gently open the door to stories we may never think to share otherwise.

Our conversation began simply enough: “When in your life have you felt happiest?” Skip reflected on his childhood—ages eight to ten—a time of freedom, discovery, and innocence. From there, the conversation naturally expanded into how world events shaped his understanding of fairness, community, and caring for others.

That’s the power of these cards. One question leads to another, not because you’re following a script, but because listening creates space for curiosity.

Stories That Shape Us

As we moved through the deck, we talked about childhood memories, favorite school subjects, first jobs, and influential teachers. We talked about humor, favorite books, and the people who make us laugh until we cry. We shared stories of travel, adventure, and the places that bring us peace.

Some moments were light and joyful. Others were deeply moving.

Skip shared the story of losing his infant daughter and the seven-year journey he and his former wife undertook to honor her memory by endowing a chair in pediatric oncology—an act of love that continues to impact families and children decades later. It was a reminder that legacy doesn’t always come from grand plans; sometimes it grows out of grief, purpose, and persistence.

These are the kinds of stories that don’t usually come up in everyday conversation—but once shared, they stay with you.

Reflection, Not Performance

One of the things I love most about these cards is that they don’t demand perfect answers. There’s no pressure to be profound or polished. The questions invite reflection, and the answers are allowed to evolve as we speak. 

When asked what words of wisdom he would share with his childhood self, Skip talked about the importance of knowing who you truly are—and living from that place rather than from others’ expectations. That insight didn’t come from preparing for the conversation; it came from being present in it.

That’s something we hear again and again from people who use the cards: they’re both lovely and challenging. They ask us to pause, reflect, and sometimes be a little vulnerable—but always in a way that feels safe and human.

Strengthening Relationships, One Question at a Time

You don’t need a podcast studio or a special occasion to use the Have the Talk of a Lifetime Conversation Cards. They work just as beautifully:

  • One-on-one with a partner or close friend
  • Around the dinner table with family
  • With adult children or aging parents
  • During holidays, reunions, or quiet evenings at home

You can pull one card or several. You can answer together or take turns. There’s no right way to do it—only your way.

In our podcast conversation, we covered less than half the deck, and by the end, Skip and I both felt we knew each other in a deeper, more meaningful way. That’s not because we learned new facts, but because we shared perspective, emotion, and experience.

Why These Conversations Matter

At Remembering A Life, we believe that how we live, love, and connect matters just as much as how we are remembered. The Have the Talk of a Lifetime Conversation Cards are one small but powerful way to honor that belief.

They help us:

  • Preserve stories before they’re lost
  • Understand the values that guide the people we love
  • Create moments of connection in a busy, distracted world
  • Build memories that matter—right now

As Skip said at the end of our conversation, the cards are both reflective and grounding. They give us an opportunity to listen more closely and to be fully present with one another.