Throughout childhood, adolescence, and early adulthood, my favorite activity was always this — talking. When I was tiny and saying my prayers before bed, my mother tells me she’d have to cut me off or I’d talk into the night. 

“Throughout childhood, adolescence, and early adulthood, my favorite activity was always this — talking.”

“Okay sweetheart, last prayer,” she’d say.

“God, thank you for my mouth.” 

Good night.

In elementary school, the only time I got “in trouble” was when I would repeatedly talk to my classmates and friends. After several warnings, I’d get moved to another spot in the classroom (only to make friends with the next unsuspecting neighbor). I loved to spend hours gabbing with my girlfriends at sleepovers until the wee hours of the morning and lived for coffee dates that stretched into the evening. I got a Communications degree. I now write words for a living.

So it’s come as a surprise when in recent years I’ve noticed it takes more of a concerted effort to handle conversational lulls. We’ll be mid-chat, the banter will come to a natural end, and where my brain would normally have an abundance of ideas of how to segue into the next topic, I simply… sip my coffee. Wait. Take another sip. 👀 What is happening?!

“Being at a loss for words is a new experience for me.”

I’m not sure if I’ve simply had less practice since 2020, am more tired than usual since becoming a mom, or I just have less bandwidth, but being at a loss for words is a new experience for me. While it’s fine to sit in the silence sometimes, other times I find myself searching for topics that I know would enrich my new relationships. There’s simply so much to learn about others and I don’t want to miss out.

Below you’ll find 99 questions to pose to carry on the conversation when you start to hear crickets chirping. These are great for getting to know someone for the first time — and even for going deeper with someone you already love. Here’s to fostering connections with meaningful conversation. ✨ 

Questions to ask on a first date

  1. Where did you grow up?
  2. What is your favorite local spot and why?
  3. What does your perfect Sunday look like?
  4. Do you have a favorite dish to cook?
  5. Do you like spicy food?
  6. Do you consider yourself religious or spiritual?
  7. How do you like to recharge at the end of a busy day?
  8. What is your astrological sign?
  9. Do you have any pets?
  10. Do you have a morning beverage and how do you take it?
  11. What is something you think is totally underrated?
  12. What is one thing on your bucket list?
  13. If you could travel anywhere in the world, where would you want to travel most?
  14. Do you play any musical instruments?
  15. What do you like to listen to when you’re in the car?
  16. What would your dream vacation consist of?
  17. Do you have any morning or evening rituals?
  18. Are you allergic to anything?
  19. Do you like to go camping?
  20. What is the last show you watched and loved?

“What is something you think is totally underrated?”

Questions to ask a new friend

  1. What is your go-to outfit, and why?
  2. Have you had your colors (seasonal color analysis) done? If so, what season are you?
  3. What is your favorite thing about yourself?
  4. What are you currently reading or looking forward to reading?
  5. What’s your favorite podcast?
  6. Do you have any tattoos?
  7. What is your favorite part of your daily routine?
  8. If you could only eat one food for breakfast for the rest of your life, what would it be?
  9. If you had to move to another country, where would you choose?
  10. Did you have a childhood nickname?
  11. Do you like celebrity gossip?
  12. What is your preferred creative outlet?
  13. You have one whole day to pamper yourself. What do you do?
  14. You have to choose five clothing items to wear for the rest of your life. What are they?
  15. What’s your biggest pet peeve?
  16. Do you like sharing food?
  17. How do you like to celebrate your birthday?
  18. Do you have a favorite family tradition?
  19. What is your preferred mode of movement?
  20. What book do you wish you could read for the first time again?

“If you could only eat one food for breakfast for the rest of your life, what would it be?”

Icebreakers for work

  1. What is your favorite thing on your desk and why?
  2. What time of day are you most fresh and productive?
  3. Where was the last place you traveled?
  4. If you had to eat the same thing for lunch for the rest of your life, what would it be?
  5. When is your birthday, and how do you like to celebrate?
  6. If you could choose an afternoon pick-me-up to be delivered to your desk every day, what would it be?
  7. What is the last book you read?
  8. What is one thing you are looking forward to?
  9. What is your favorite holiday?
  10. Do you speak any languages other than English?
  11. If you could be fluent in a language you do not know, what would it be? 
  12. Do you have any dietary restrictions?
  13. What is your screensaver/lock screen photo?
  14. What is your commute like (drive, carpool, public transport, walk)?
  15. What was your first ever job?

“What was your first ever job?”

Vulnerable icebreakers

  1. When do you feel most cringe? (For example, I feel cringe when I realize I’m overexplaining myself when no one asked. Oops!)
  2. Do you know your attachment style? If so, what is it?
  3. What is your Enneagram number?
  4. When you feel dysregulated, how do you get grounded?
  5. What is your earliest memory?
  6. When have you felt most alive?
  7. When you’re looking for comfort, who is the first person you call?
  8. What are you struggling to let go of?
  9. Who was your first kiss?
  10. If you didn’t have any responsibilities, how would you spend your days?
  11. Do you enjoy solo travel? 
  12. If you could go on a personal retreat, what would you do?
  13. In which area do you need rest? (Physical, mental, spiritual, etc.)
  14. What do you need to forgive yourself for?
  15. What do you love most about yourself? (Be generous!)

“When you’re looking for comfort, who is the first person you call?”

Silly icebreakers

  1. Do you sleep with a top sheet?
  2. What is your guilty pleasure?
  3. What is your Roman Empire? (aka something you think about a lot)
  4. If you won the lottery, how would you spend your winnings?
  5. If you could only watch one show for the rest of your life, what would it be?
  6. If you had the chance to go to outer space, would you do it?
  7. Do you have any secret talents?
  8. Do you know what your parents would have named you if they hadn’t chosen your name?
  9. Have you ever egged someone’s house?
  10. Have you ever 💩your pants?
  11. Do you believe in aliens?
  12. Have you ever laughed so hard you spit out your drink?
  13. Have you ever met a celebrity?
  14. Did you have an imaginary friend as a child?
  15. If you could have one superpower, what would it be?

“Do you know what your parents would have named you if they hadn’t chosen your name?”

This or that?

  1. Early bird or night owl?
  2. Sweet, savory, or sour?
  3. Work from home or in person?
  4. Personal driver or a personal chef?
  5. Lifetime free travel or lifetime free food?
  6. Silence or background noise?
  7. Going out or staying in?
  8. Minimalist or maximalist?
  9. Saver or spender?
  10. Cocktail or mocktail?
  11. Vacation or staycation?
  12. Sparkling or still?
  13. Window or aisle seat?
  14. Silver, gold, or both?

“Lifetime free travel or lifetime free food?”

Kate Arceo is Community Manager at The Good Trade. When she’s not hosting dinner parties with her husband at their home in Southern California, you can find her sipping a latte at their local coffee house or shopping for strawberries with her kids at the farmers market. Say hi on Instagram!