19 Juicy Questions To Ask Your Friends The Next Time You Get Together

If you and your friends have known each other for a while, shared your deepest childhood secrets, and talk all the time, it’s easy to assume that you know everything there is to know about them. But chances are, that’s not really the case — you just need to be a little creative and come up with some juicy questions to ask.

“Now more than ever, we're craving connection,” Michaela Bucchianeri, PhD, LP, a licensed psychologist and anxiety coach, tells Bustle. “Anything that moves your conversation beyond a surface-level check-in has the potential to create shared meaning, uncover surprises, and deepen your connections to the people you've known forever.”

According Bucchianeri, it’s important to keep making a conscious effort to connect with friends on a deeper level. If you don’t, “our conversations with friends can easily lapse into the same cycle of updates (e.g. ‘What's new with you lately?’ ‘How's work these days?’ ‘I saw your photos on Instagram... looks like it was a fun trip,’ etc.)” she says. “This can leave us feeling surprisingly disconnected, and unsure why. You've just spent an evening catching up with your best friend, and yet you feel dissatisfied, like there was no real heartbeat to the conversation.”

Asking thoughtful questions can prevent that and keep your friendship strong. Plus, it’s alway a lot of fun to learn things about your friends that you never knew. So here are some expert-approved juicy questions to ask your friends next time you get together.

Get Nostalgic

According to Bucchianeri, juicy questions don’t have to be complicated or intense, especially if you’re getting together for a much-needed break or a night out. She suggests asking questions that can take you down memory lane.

1. If our friendship were a playlist, what would you name it and why?

2. What’s one memory of the two of us that you look back on and cringe?

3. Who’s someone you had a crush on but never told me about?

4. What part of your childhood do you miss most?

5. What’s one piece of love advice you’d tell your younger self?

Put Yourself In The Hot Seat

After asking your friend questions about themselves, Bucchianeri suggests “flipping the script” and placing yourself in the hot seat.

6. What's something you've always been curious to ask me?

7. What did you really think of me when we first met?

8. What’s the longest you’ve ever been mad at me and what did I do?

9. Why do you think you and I are such good friends?

10. If there’s one thing you could change about me, what would it be?

“In the end, it's not really about the specific questions themselves,” Bucchianeri says. “It's about the intention behind them and the willingness to be open and attentive to the answers.”

Ask Vulnerable Questions

If you want to deepen your friendship, Heidi McBain, licensed marriage and family therapist, suggests asking questions that allow both you and your friend to be open and vulnerable.

11. How would your therapist describe you?

12. What is something you dislike about yourself?

13. Who would you say is the one person who’s hurt you the most in your life?

14. What was your biggest insecurity growing up? How do you feel about it now?

15. Where do you hope to be 10 years from now?

Get Playful

Shared laughter is another way to bond with friends, so both Bucchianeri and McBain suggest asking playful questions. No need to overthink, just have fun with it.

16. What’s your most embarrassing moment as an adult?

17. What’s the most ridiculous thing you’ve ever gotten away with?

18. What’s the weirdest date you’ve ever been on?

19. What do you think we’ll look like when we’re 60?

Sources

Michaela Bucchianeri, PhD, LP, a licensed psychologist and anxiety coach

Heidi McBain, licensed marriage and family therapist