Funny Questions to Ask Grandma: 60+ Hilarious Conversation Starters

Article Snapshot

• Funny questions help grandma relax and share stories she might not otherwise tell
• Humor opens the door to deeper conversations about her life and experiences
• Questions about embarrassing moments and youthful adventures reveal her personality
• Lighthearted conversations create lasting memories for everyone involved
• Recording grandma's funny stories preserves her humor for future generations

Your grandma has stories you've never heard. She was young once. She made mistakes. She laughed until she cried and did things she probably shouldn't have. The problem is, no one asks her about the fun stuff.

I have gathered 60+ funny questions that get grandma talking about the lighter side of life. These conversation starters work at family dinners, during visits, or on phone calls when you want more than the usual updates. The goal is simple: get her laughing and telling stories.

For a complete collection of questions for grandma and other family members, visit our Questions to Ask Family Members guide with 640+ prompts for every occasion.

Funny Questions About Her Youth

Grandma wasn't always a grandma. She was a kid, a teenager, a young adult with dreams and crushes and questionable decisions. These questions reveal that version of her.

• What did you get in trouble for that your parents never found out about?
• What is the greatest prank you ever pulled?
• Did you ever sneak out of the house? What happened?
• Did you have a curfew? What time was it, and did you ever break it?
• Who was your first crush? Did they know?
• Who was your first kiss? What's the embarrassing story behind it?
• What was the worst date you ever went on?
• What did you and your friends do for fun in high school?
• Which teacher did you drive the most crazy in school?
• What car did you desperately want but couldn't afford?

Questions about her youth often lead to the best stories. Grandma might reveal she was much wilder than you ever imagined.

Embarrassing Moments and Regrets

Everyone has cringe-worthy memories. These questions help grandma laugh at her younger self.

• What fashion trend do you regret following?
• What's the worst haircut you ever had?
• What's an embarrassing moment that still makes you laugh or cringe?
• What's the most embarrassing song you know all the words to?
• What was your most embarrassing moment as a young adult?
• Did you ever accidentally say something at the wrong time?
• What celebrity did you have a crush on that embarrasses you now?
• What did you think was cool that definitely wasn't?
• What photograph of you should never be seen by anyone?
• What nickname did you hate but couldn't shake?

Embarrassment questions usually get big laughs. Grandma might share a photo or story that changes how you see her.

Questions About Love and Marriage

Grandma's love life has plenty of material for funny stories. These questions reveal the lighter side of romance.

• What's the funniest argument you ever had with your spouse?
• How did you really meet Grandpa? Is it different from the official story?
• What drove you crazy about Grandpa when you were dating?
• What's the worst gift Grandpa ever gave you?
• What habit of Grandpa's took the longest to accept?
• What's the biggest fight you ever had about something ridiculous?
• Did Grandpa ever try to cook for you? How did that go?
• What's the worst fashion choice Grandpa ever made?
• What did your parents think of Grandpa when they first met him?

Marriage questions often reveal decades of stored-up stories. Grandma might finally tell you what she really thought of grandpa's mustache in 1972.

Questions About Parenting

Grandma raised your parents. She has stories they definitely don't want you to hear. These questions uncover them.

• What's the most ridiculous thing my parent did as a kid?
• What did my parent get in trouble for the most?
• What lie did my parent tell that you knew was a lie?
• What was my parent's most embarrassing phase?
• What moment made you think "I have no idea what I'm doing" as a parent?
• What parenting mistake can you laugh about now?
• What did you let your kids get away with that you shouldn't have?
• What family secret were you supposed to keep from the kids?
• What did you secretly enjoy about your kids getting in trouble?

Parenting questions are gold. Your parent will probably try to stop grandma from answering, which makes it even funnier.

Life Lessons Learned the Hard Way

Some of life's best lessons come through funny failures. These questions capture wisdom wrapped in humor.

• What's the weirdest thing you believed as a kid?
• What life advice do you wish you had ignored?
• What's a mistake you made that you'd make again?
• What did you think would be easy that turned out to be hard?
• What technology confused you the most?
• What cooking disaster still gets talked about?
• What's the worst purchase decision you ever made?
• What warning from your own parents turned out to be right?

Hard-earned lessons often make the funniest stories. Grandma might share disasters that shaped her wisdom.

Random Funny Questions

Sometimes the best conversations come from unexpected questions. These have no particular theme except getting grandma to laugh.

• What silly tradition have you shared with friends or family over the years?
• What joke, prank, or inside joke still makes you smile?
• Do you remember a time when you laughed so hard you cried?
• What's the most useless talent you have?
• What food did you pretend to like for way too long?
• What's something you're surprisingly competitive about?
• What popular thing have you never understood the appeal of?
• What would your wrestling entrance song be?
• If you could break any rule without consequences, which would it be?
• What would your reality TV show be called?

Random questions often catch grandma off guard in the best way. Her answers might surprise everyone, including herself.

Questions to Ask at Family Gatherings

Family gatherings are perfect for getting grandma to tell stories in front of an audience. These questions play well to a crowd.

• What's a family secret that's okay to share now?
• Who in the family is most like you when you were young?
• What family member do you have the funniest stories about?
• What's the best prank ever pulled at a family gathering?
• What family recipe did someone ruin memorably?
• What family tradition should we bring back?
• What's the most ridiculous family argument you remember?

Making Grandma Conversations Fun

Here are tips for getting the best stories out of grandma:

Ask when she's relaxed. After dinner or during a quiet visit works better than rushed moments.

Be genuinely curious. Grandma knows when you're going through the motions. Show real interest in her answers.

Follow up on interesting details. When she mentions something intriguing, ask more. "Wait, what happened next?"

Record the conversation. With her permission, capture these stories on video. Future generations will treasure seeing grandma laugh and tell stories.

Share your own embarrassing moments. Grandma might open up more if you go first with your own funny confession.

For more conversation ideas, explore our complete guide to questions for family members with 640+ prompts.

Why Grandma's Funny Stories Matter

Humor reveals character. The way grandma laughs, what makes her cringe, the stories she finds funny. All of this shows who she really is beyond the grandma role you know.

At Telloom, we help families capture grandma's personality through guided video conversations. Our prompts include "Laughter and Light Moments" alongside deeper life story questions. But whether you use professional services or just call her with a silly question, what matters is hearing her laugh and preserving that sound.

Your grandma has stories she's never told anyone. Adventures, mishaps, romances, and ridiculous moments from decades of living. All you have to do is ask.

Call grandma. Make her laugh. Record the stories. You'll both be glad you did.