Why ‘Would You Rather’ Questions Strengthen Family Relationships

Andrew Ronald

Simirity Founder | Father of two

10th February, 2026

I love talking with my two boys, but if I’m honest, most of our conversations are practical rather than memorable. We talk about homework. Weekend plans. What’s for dinner. Important? Yes. Revealing and memorable? Rarely.

Fortunately, I found a shortcut to great conversations that strengthen family relationships: using ‘would you rather’ questions that explore a mind-blowing range of topics we’d never naturally discuss. These conversations are far more than just ‘fun’. By asking follow-up questions about people’s answers, we all gain fantastic insights into each other’s characters and values.

I recommend all parents try out would you rather questions with their children—it’s such an easy way to feel closer to your kids.

The Modern Family Challenge

Like many modern families, we face challenges our parents’ generation didn’t— demanding schedules, geographic distance, and the constant pull of screens.

Finding moments for genuine conversation takes more intention than it used to. That’s partly why these questions became so valuable to us—they create structured opportunities for connection that might not happen otherwise.

What Are Would You Rather Questions?

When was the last time you went deeper than the usual conversations with your kids, and explored their core values and beliefs?

These topics don’t tend to come up naturally. That’s where would you rather questions excel. They present an intriguing set of options, where people have to choose between two scenarios, creating gentle pressure to prioritise what matters.

For instance:

• “Would you rather have the ability to fly or be invisible?” — forces kids to choose between power and privacy
• “Would you rather give up social media for a year or give up TV for a year?” — reveals which digital habit has deeper roots
• “Would you rather always tell the truth or always be kind?” — exposes emerging values about honesty versus compassion

"We are our choices."

— Jean-Paul Sartre

People’s answers to the would you rather questions can reveal who they are beneath the surface.

The greatest insight comes by asking: “Why did you choose that?” This single question turns a playful exercise into a meaningful exploration of personality, fears, and priorities that rarely surface in routine conversations.

Want to explore a few more would you rather questions? Take turns spinning the wheel to discover random questions from our collection—it’s a fun way to sample the range of topics these questions explore.

Ready to dive deeper? Browse our complete collection of 300+ would you rather questions organised by theme, from lighthearted fun to thought-provoking dilemmas designed specifically for families.

The Psychology: Why These Questions Work So Well

These questions work so well because they operate differently to normal conversations.

• Instead of asking how someone feels or what they think about something, they reveal their priorities through a simple choice.
• Instead of directly questioning someone which can feel like interrogation, they create playful distance that makes it far easier to be honest. It’s all hypothetical after all!

Go beyond “How are you?”—truly connect with family.

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Four Ways Would You Rather Questions Strengthen Family Relationships

Understanding how would you rather questions can strengthen families, will help you use them more effectively. Here are four key benefits you will enjoy:

1. Deeper understanding of people’s values and character

Five minutes of these questions has taught me more about my kids’ actual values than weeks of “How was your day?” The format cuts through deflection and reveals the real person underneath.

2. Learning opportunities based on stories

When adults explain their choices, they’re sharing experiences, not delivering lectures. When I tell my kids why I’d “rather admit a mistake than cover it up,” they hear the story of when I learned that lesson the hard way—and that sticks. The message about what’s right and wrong, what we value and what we don’t, gets received without the resistance that comes from being told what to think. Stories teach what rules can’t.

Research shows this storytelling approach works: studies from the University of Nevada Extension found that when parents share family stories through conversation, children view their family as stronger, show higher self-esteem, and demonstrate better ability to handle stress.

3. Memorable conversations that help with future decisions

These conversations become reference points your children carry with them.

When my son faced a situation where friends pressured him to exclude someone, he didn’t recall me saying “be kind”—he remembered our conversation based on the question “Would you rather be popular or be someone people trust?”, and the real-life stories we’d shared. That’s the power of these discussions: they create anchors that help young minds make good decisions or seek out family members with relevant experience when challenges arise.

4. Conversations that connect all generations

The magic of questions that work for all ages isn’t just inclusion—it’s mutual discovery.

Young children learn how their grandparents think, not through old stories but through present-day choices that reveal character and values. When a seven-year-old hears their seventy-year-old grandparent explain their reasoning, they’re gaining respect for someone whose world feels completely different from their own.

Meanwhile, grandparents get something they rarely receive: genuine access to their grandchildren’s inner lives. Not what they did at school, but how they think, what they value and a deeper insight into their character.

And frequently, families discover their values have naturally aligned across generations. When children see that parents, aunts, uncles, cousins, and grandparents all answer similarly, those shared values carry far more weight than if they’d simply been told “this is what our family believes.” Though when answers differ, that creates valuable conversations too—exploring why values sometimes shift across generations.

Connect every generation through the power of storytelling.

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Three Tips for Best Family Conversations

1. Start casually—don’t make it a “thing.” The best conversations happen organically. Drop a question during car rides, while cooking dinner, or when normal conversation naturally lulls. “Hey, would you rather…” feels like play, not scheduled family bonding time.
2. Choose settings where you’re side-by-side. Car journeys are perfect because you’re together but not staring at each other. Walking, doing dishes, waiting for food—parallel activities create space for honesty in ways face-to-face conversation sometimes can’t.
3. Let some questions be light, others deep. Not every question needs to spark a profound discussion. Some will get quick answers and move on—that’s fine. The habit of these conversations matters more than making every single one meaningful. Over time, your family learns these talks are safe, fun, and worth having.

Ready to get started? Browse the full collection of 300+ would you rather questions for families.

Other Ways to Strengthen Family Relationships

Would you rather questions are one powerful tool for deeper family conversations. If you’re discovering the value of intentional question-asking, you might also enjoy:

1. 150+ questions to ask your kids for one-on-one moments that reveal their inner world—friendships, dreams, worries, and how they see themselves.
2. 350+ questions to ask your mom and your dad that explore their past, values, and life experiences before those stories are lost.
3. Best family journal ideas for identifying precious family stories worth preserving.
4. The ‘first last best worst’ storytelling game that uses prompts to uncover untold family stories.

Each approach creates different pathways to understanding the people you love—try them all and discover what resonates with your family.

Your family’s past, present & future—woven together in Simirity.

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