30 Genius Ways To “Guess” Your Way To The Best Moments

Let’s face it, sometimes striking up a conversation with our tech-savvy, TikTok-loving grandkids can feel like learning a new language. Sure, asking about school or their favorite food can get the ball rolling, but let’s spice things up a bit.

Introducing the Guessing Game. This isn’t just a list of questions; it’s a fun-filled journey into each other’s lives. Imagine the joy when you find out you both share the same comfort food or the laughs that ensue when you both reveal your “signature dance moves.”

Here’s how to get the most out of it:

1. The Element of Surprise: Don’t just ask the question—make it a game! See if they can guess your answer and vice versa.
2. Follow-Up Fun: Each main question comes with a set of follow-up questions to keep the chatter going.
3. All Ages Welcome: Whether they’re tots or teens, there’s something for every grandchild to engage with.
4. No Pressure: Remember, this is all about fun and connection. There’s no wrong answer!

What Was My Go-To Playground Game as a Child?

This question helps bridge the generational gap by discussing the games you enjoyed as a child, offering a comparison to the games your grandchild enjoys now.

Follow-up Questions:

• “Why do you think that game was my favorite?”
• “What’s your favorite playground game?”
• “Would you have played my favorite game?”
• “Can you name a game you think is similar today?”

Can You Guess the First Movie I Saw in a Theater?

Movies are a common interest across generations. This question can lead to a conversation about how movies have evolved over time.

Follow-up Questions:

• “Why did you guess that movie?”
• “What’s the first movie you remember seeing in a theater?”
• “Do you think I’d like your first movie?”
• “What genre do you think the movie was?”

Guess What My First Job Was?

Discussing your first job can open up a conversation about work ethics, interests, and aspirations.

Follow-up Questions:

• “Why do you think I chose that job?”
• “What’s a job you’d love to have one day?”
• “What’s the most unusual job you can think of?”
• “Would you have liked my first job?”

What Animal Am I Most Afraid Of?

An easy way to talk about fears in a non-threatening manner and may lead to conversations about overcoming fears.

Follow-up Questions:

• “Why did you pick that animal?”
• “What animal are you afraid of?”
• “Do you know anyone who has that animal as a pet?”
• “Have you ever seen that animal in real life?”

Guess My Favorite Type of Dance?

Discussing the arts can open doors to conversations about different cultural practices, music, and physical activities.

Follow-up Questions:

• “Why do you think that’s my favorite dance?”
• “Do you have a favorite dance or dance move?”
• “Have you ever wanted to take dance classes?”
• “Do you think that dance style has changed over the years?”

Can You Guess My Favorite Holiday?

Holidays often bring back fond memories. This can be a great way to reminisce and share traditions.

Follow-up Questions:

• “Why did you guess that holiday?”
• “What’s your favorite holiday and why?”
• “Is there a holiday you wish you could create?”
• “What’s a holiday tradition you love?”

What Sport Did I Play When I Was Your Age?

Engage your grandchild in a discussion about sports and physical activities that interest both of you.

Follow-up Questions:

• “Why do you think I played that sport?”
• “Do you play any sports or wish to?”
• “Who’s your favorite athlete?”
• “Would you want to try the sport I played?”

Guess the Name of My First Pet?

Pets are often an interesting and emotionally safe topic to explore. Discuss the responsibilities and joys that come with pet ownership.

Follow-up Questions:

• “Why did you guess that name?”
• “Do you want a pet or do you have one?”
• “What would you name your ideal pet?”
• “What kind of pet do you think I should have now?”

What’s My Go-To Karaoke Song?

Music connects people. Discuss different musical tastes and perhaps find common ground or new music to enjoy.

Follow-up Questions:

• “Why did you guess that song?”
• “Do you have a favorite song?”
• “What song makes you dance?”
• “Do you think our musical tastes are similar?”

Can You Guess Where I Went on My First Trip Alone?

Travel is an excellent way to discuss freedom, responsibility, and broaden horizons about different places.

Follow-up Questions:

• “Why did you pick that location?”
• “Where would you like to go on your first solo trip?”
• “Do you prefer the beach or the mountains?”
• “What’s the most exotic place you want to visit?”

What Was My Childhood Dream Job?

Discussing dream jobs can provide a window into each other’s aspirations and passions.

Follow-up Questions:

• “Why did you guess that job?”
• “What’s your dream job?”
• “Do you know anyone who has my dream job?”
• “How different is my dream job from what I actually did?”

Can You Guess My All-Time Favorite Book?

Books can serve as a bridge between imagination and experience, perfect for starting meaningful conversations.

Follow-up Questions:

• “Why did you pick that book?”
• “What’s your favorite book?”
• “Do you think the favorite book tells something about a person?”
• “Have you read anything good lately?”

What Instrument Do I Wish I Could Play?

Talk about musical interests and perhaps discover a shared passion for music.

Follow-up Questions:

• “Why did you choose that instrument?”
• “Do you play any instruments?”
• “Would you like to learn an instrument together?”
• “What’s your favorite musical genre?”

Guess My Favorite Childhood TV Show?

Discussing television shows can lead to a fun and nostalgic conversation.

Follow-up Questions:

• “Why did you guess that show?”
• “What’s your favorite TV show right now?”
• “Would you watch my favorite show if it were still on?”
• “Do you think TV shows were better in the past?”

What Was My Favorite Subject in College?

This can lead to talks about academic interests, career paths, and personal development.

Follow-up Questions:

• “Why did you guess that subject?”
• “What subject do you think you’ll like in college?”
• “Do you think college is important for everyone?”
• “Do you think you’d enjoy my favorite subject?”

Guess the First Car I Ever Owned?

Cars can be more than just transportation; they often carry significant memories.

Follow-up Questions:

• “Why did you choose that car?”
• “What kind of car do you see yourself driving?”
• “Manual or automatic—which do you think I prefer?”
• “What’s your dream car?”

Can You Guess My Favorite Season?

Seasons influence our mood, activities, and even food. This can lead to a range of topics to discuss.

Follow-up Questions:

• “Why did you pick that season?”
• “What’s your favorite season and why?”
• “Which season do you think has the best holidays?”
• “Do you have a favorite seasonal activity?”

What’s My Go-To Comfort Food?

Discussing food preferences can lead to conversations about culture, comfort, and even cooking together.

Follow-up Questions:

• “Why did you guess that food?”
• “What’s your comfort food?”
• “Have you ever tried making my comfort food?”
• “Do you want to cook it together sometime?”

What’s My Signature Dance Move?

A lighthearted question that can lead to funny revelations and perhaps even a mini dance-off.

Follow-up Questions:

• “Why did you guess that move?”
• “Do you have a signature dance move?”
• “Who in the family is the best dancer?”
• “Would you join me for a dance?”

What’s My Favorite Board Game?

Board games are a great way to bond. This question can lead to an actual game night.

Follow-up Questions:

• “Why did you choose that game?”
• “Do you have a favorite board game?”
• “Who usually wins when we play?”
• “What’s a game you think we should get?”

What Was My Childhood Nickname?

Nicknames often have stories behind them. This can open the door to funny or heartfelt stories from both sides.

Follow-up Questions:

• “Why did you guess that nickname?”
• “Do you have a nickname?”
• “How do you feel about nicknames?”
• “Would you like to know the story behind mine?”

Guess My Favorite Type of Tree?

A unique question that can lead to discussions about nature, hobbies like gardening, or even environmental issues.

Follow-up Questions:

• “Why did you choose that tree?”
• “Do you have a favorite plant or tree?”
• “Do you know the state or national tree?”
• “Have you ever planted a tree?”

What Sport Do You Think I’m Terrible At?

This question is a fun, humble way to discuss skills and talents, maybe even leading to trying a new sport together.

Follow-up Questions:

• “Why did you pick that sport?”
• “Is there a sport you think you’re not good at?”
• “What’s a sport you’d like to try?”
• “Do you think athletic talent is natural or learned?”

Guess My Favorite Ice Cream Flavor?

Everyone has a favorite ice cream, making this question a delicious way to learn more about each other.

Follow-up Questions:

• “Why did you choose that flavor?”
• “What’s your all-time favorite ice cream?”
• “Have you ever tried making ice cream?”
• “What’s a flavor you wish existed?”

What’s My Go-To Joke?

A light-hearted question that can lead to a lot of laughs and sharing of jokes.

Follow-up Questions:

• “Why did you guess that joke?”
• “Do you have a go-to joke?”
• “Who’s the funniest person you know?”
• “Do you think humor is important?”

Guess My Favorite Cartoon Character?

Discussing favorite characters can lead to a conversation about values, traits admired, and shared interests in shows.

Follow-up Questions:

• “Why did you pick that character?”
• “Do you have a favorite character?”
• “What character traits do you admire?”
• “Do you like the same type of shows I do?”

Can You Guess My Zodiac Sign?

This could lead to a fun discussion about personality traits associated with zodiac signs, whether you believe in them or not.

Follow-up Questions:

• “Why did you guess that sign?”
• “Do you think zodiac signs are accurate?”
• “What’s your sign and do you think it fits you?”
• “Have you ever read your horoscope?”

What’s My Favorite Type of Weather?

This can lead to conversations about ideal vacations, favorite outdoor activities, or even personal comfort preferences.

Follow-up Questions:

• “Why did you pick that weather?”
• “Do you prefer hot or cold?”
• “What’s your favorite outdoor activity?”
• “Do you have any special weather memories?”

Guess My All-Time Favorite Band?

This question can serve as a gateway to a shared playlist or introduce each other to new music.

Follow-up Questions:

• “Why did you choose that band?”
• “Do you have a favorite band or artist?”
• “Have you ever been to a concert?”
• “Do you think music was better in my time?”

What Is My Morning Ritual?

This question can serve as a window into daily lives, routines, and how each starts the day.

Follow-up Questions:

• “Why did you guess that ritual?”
• “Do you have a morning routine?”
• “What’s the best way to start the day?”
• “Do you consider yourself a morning person?”

Remember, the best conversations often happen when we least expect them.

So keep this list handy for car rides, weekend visits, or even those moments when you’re both snuggled on the couch scrolling through your respective screens. Let’s turn those thumbs into talks!