7 Best Times to Use Family Conversation Starters

Andrew Ronald

Simirity Founder | Father of two

11th February, 2026

Collecting good family conversation starters is easy—but finding the right time to slot them into your busy family schedule is hard…

I learned this the hard way after collecting dozens of “entertaining questions for kids” that sat unused for weeks. Then I discovered ‘would you rather’ questions—and, more importantly, I took the time to figure out when to use them. Once I mapped them to specific moments (e.g. dinners, car rides), the conversations finally started flowing.

Below are seven tried-and-tested times when family conversation starters can transform ordinary moments into fun and engaging conversations.

Why ‘Would You Rather’ Questions are The Best Family Conversation Starter

Most conversation prompts I’ve tried with my kids fall into two camps: too simple or vague (“How was your day?”) or too complex (“If you could solve one world problem, what would it be?”).

‘Would you rather’ questions hit the sweet spot. They work by presenting two choices that reveal what someone values—not through interrogation, but through playful decision-making.

Here are a few examples:

• “Would you rather be able to fly or turn invisible?” → Your child explains why freedom matters more than hiding, or vice versa
• “Would you rather always tell the truth or always be kind?” → You discover their instincts about honesty versus protecting feelings
• “Would you rather give up social media or TV for a year?” → You learn which actually has more grip on their daily life

The real conversation starts with: “Why did you choose that?” This turns a simple choice into a window into their thinking.

Want to know more about how these questions strengthen family relationships? We’ve explored this in detail.

Test it yourself: Spin the wheel to try random questions from our collection:

For the full library, browse our complete collection of 300+ family-friendly questions organised by topic.

The 7 Best Times to Ask These Questions

Here are my family’s favourite times for using these questions.

1. Sunday dinner table tradition

The scenario: At Sunday dinner, one family member picks three questions to ask during the meal.

Why this works:

• Creates a predictable routine that everyone looks forward to
• Gives each person a turn at leading the conversation
• Transforms the quietest meal of the week into the most memorable

How we do it: In our house, it’s usually me picking the questions, but ideally you would take turns so everyone has their turn at leading the conversation and selecting the questions that they find most interesting. It doesn’t happen every week, but I know the kids like it as they keep asking for it!

2. Long car journey entertainment

The scenario: Road trips lasting two hours or more.

Why this works:

• Requires zero materials—just voices and imagination
• Everyone participates equally (even the driver)
• Time passes surprisingly quickly when everyone’s engaged

How we do it: We usually start around the one-hour mark, when the initial conversations have died down. Sometimes we would make up our own questions and other times we’d refer to the list of 300 questions. Some questions pass by within a minute, while others keep us engaged and debating for several miles of the drive.

3. Video call with distant grandparents

The scenario: Weekly or monthly video calls between grandchildren and grandparents who live far away.

Why this works:

• Gives structure to calls that often sees children’s attention wane and run off and do something else
• Helps grandparents and grandchildren get to know each other far better
• Creates shared talking points that last beyond the call

How we do it: My parents and my sister’s family live in different countries from us. We have our regular calls, and try to involve the kids whenever possible. When we’ve covered the usual catch-up call topics, if time allows, we get into the habit of throwing in a few ” Would You Rather ” questions to keep the kids interested and participating in the call. It felt a little strange at first, but the kids cite this as the best part of the calls, and often, I have to agree, they are not wrong!

4. Holiday gathering icebreaker

The scenario: Christmas, Thanksgiving, or family reunions when extended family gathers and conversation feels forced.

Why this works:

• Breaks awkwardness between cousins who rarely see each other
• Gives shy family members an easy way to participate
• Creates laughter and connection across different ages

How we do it: I assume the role as the question master, and I usually prepare a dozen or so questions that I think everyone will enjoy. They work very well as an icebreaker after the initial welcomes, and once everyone’s settled in perhaps with a cup of tea and cake by your side. It’s fun for us as adults, but the main benefit is gently reconnecting the kids with extended family that they don’t see so often.

5. Bedtime wind-down conversation

The scenario: The last 10 minutes before lights out, when kids are calm and often more open to talking.

Why this works:

• Creates a peaceful transition from activity to sleep
• One-on-one time with each child
• Kids often share more in these quiet moments

How we do it: We don’t have it as a nightly thing, but periodically when the mood feels right, we’ll ask a few questions to get a gentle and calm conversation flowing. You have to be careful, of course, as you don’t want to get them all excited, so we pick our questions wisely.

6. Playdate icebreaker (new friends)

The scenario: When your child has a friend over and they haven’t quite bonded yet.

Why this works:

• Provides structure without being obvious
• Helps kids discover shared interests
• Eases parental anxiety about whether kids are getting along

How we do it: No need to jump into the questions right away if they’re having a great time, so you just stand by and see how they get on. If you can see that they’re not quite sure what to do, we sit them down with a drink and I explain the game and pick some suitably funny and entertaining questions to get started with. We usually only need half a dozen or so before they’ve connected and are ready to go on and play.

7. Rainy day activity

The scenario: Unexpected indoor days when outdoor plans are canceled and everyone’s disappointed.

Why this works:

• No preparation needed—questions work anytime
• Turns boredom into connection
• Lifts mood through engagement

How we do it: When it’s apparent the kids are bored and crying out for tablet time, this question game is a great delaying tactic that shifts their focus.

Making It a Habit (Not a One-Time Thing)

The difference between trying to use family conversation starters once and making them part of family life comes down to starting small.

Pick just one scenario from this list—whichever fits most naturally into your current routine. Use it consistently for a few weeks, and let family members get comfortable with the format.

I suspect once you’ve tried it once, your kids will remind you to try it again on subsequent occasions. Ultimately, the challenge is having enough questions to keep these conversations flowing!

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

SEE HOW

Tips For This Questioning Game

1. Prepare your questions beforehand

If possible don’t wing it—choose 5-10 questions before you start. Print them, bookmark them on your phone, or add them to your phone notes so they are always available.

When the moment hits and you want to get stuck into the questions, you really don’t want to scramble to think of one and risk having the momentum die. Having questions ready keeps energy high.

2. Start with easy icebreakers

Begin with obviously fun questions (“Would you rather spend a day exploring space on a rocket ship or diving deep in a submarine?”) before moving to deeper ones (“Would you rather be feared or loved?”). This warms everyone up and establishes that the activity is enjoyable, not interrogation. Save thoughtful questions for later in the session.

3. Use the spinner wheel for spontaneity

If choosing questions feels like too much work, let randomness handle it. The spinner wheel picks questions for you—kids especially love the surprise element. It removes decision paralysis and keeps things moving.

4. Always ask “Why did you choose that?”

The real value of this game isn’t in the initial answer—it’s in the explanation.

When someone says “I’d rather explore space on a rocket,” ask “Why?” or “Where would you go?” These follow-ups transform simple choices into priceless conversations. This is where you learn how your family really thinks.

5. Take turns being question master

Let different family members lead each session.

When kids choose questions, they feel ownership. When grandparents choose, they guide conversations toward topics they value. Rotating this role prevents one person from dominating and keeps everyone engaged.

6. Keep the tone playful, not serious

These work best when they feel like a game, not a must-do task enforced by mom or dad.

Laugh at silly answers. Don’t correct “wrong” reasoning. The moment it feels like a test or therapy session, kids disengage. Fun and lightness create the safety for deeper sharing to happen naturally.

7. Preserve answers for the future

Some of these conversations will be priceless in 10 years.

Record audio on your phone, shoot quick videos, or write answers in Simirity Family Journal alongside photos from that time. Future you—and future them—will treasure hearing how they answered the questions at age 7, or 14, or 40.

Our Family-Friendly List of Would You Rather Questions

Our collection of 300+ questions was built specifically for families, and refined through countless hours of real family conversations.

We’ve removed the overly silly questions that frustrate adults (e.g. ‘Would you rather sneeze glitter or burp rainbows?’) and avoided anything inappropriate, creating a list that works for everyone from age 12 to great-grandparents. You’ll find questions that make people laugh, questions that reveal values, and questions that spark genuine curiosity about each other.

If you want a resource that actually strengthens family relationships—not just kills time—this is it.

Other Ways to Strengthen Family Connections

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.

Family is forever—make sure their stories are too.

SIMIRITY JOURNAL