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20 Best Deep Questions To Ask Friends - One Dive To Know Them Quick!

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Jasper is our expert conversationalist and wordsmith. He loves coming up with questions, jokes, and topics designed to create natural conversation. His work has been featured on Marriage.com, iHeart Media, Elite Dai ...
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by | | August 25, 2021


This post is about the deep questions to ask friends that you should be asking.

When it comes to deep conversation starters and having a meaningful conversation, I'm your guy. Any deep conversation topic sparks interest in our readers. So, the thoughtful questions you need are right here.

This list will be all you need to stray away from any awkward silence. Let's dive into it!

Contents

4 Interesting Things To To Talk About With Your Best Buddies

The best questions you can ask your friends are those that can spark some interpersonal closeness. Meaningful questions drive a good conversation. These are all the best deep questions to ask if you want to keep that discussion flowing.

Here are the 4 best deep questions to ask:

1. What gives you the most comfort?

This one also works as a great conversation starter. Personal questions like this give you a deeper look into someone's personality. What makes them who they are?

2. What do you dislike the most in people?

This is not only deep, but it's also a fun question! Sometimes, we can bond over our shared dislikes in people. This is a good question to find some common ground, maybe.

3. What is your biggest fear?

They say that our biggest fear causes our biggest regret. This is an important question to take note of. It's essential to know your friends' biggest fear to either help them get through it or respect it and help them accept it.

4. Would you rather have infinite money or eternal love?

This is one of those icebreaker questions that can get you thinking. There's no room for small talk with something like this.

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4 Conversation Topics For A Stronger Friendship

Deep questions don't always have to be serious. They can be fun and exciting. If you want to create a lasting friendship, ask your conversation partner these interesting questions! Don't worry. They're generally polite conversation topics.

Here are 4 deep, interesting questions to ask friends:

5. What do you hope to achieve by the age of 50?

This open ended question can be the start of deeper conversations. Find out what their biggest dreams are with this one.

6. If you could do anything for the rest of your life, what would that be?

This one is an interesting question! Do you know your answer to this one? What's a favorite thing of yours to do that you're willing to do forever?

7. What do you miss most about being a kid?

This is a cute question! We all have a favorite memory from when we were kids. There's always that one memory that makes us want to be kids again.

8. If you could slow down time, what would you do with that power?

This random question is fun! Having any superpower is interesting. What would you do if you had one?

3 Fun Would Your Rather Probe For Your Pals

If you decide to use would you rather questions as your questions to know someone deeper, you can expect tons of fun! Hint: They can be funny questions, too! Does your conversation fizzle all the time? Expect none of that with these!

Here are 3 deep would you rather questions to ask friends:

9. Would you rather change the past or see the future?

This one's a great question! The past is a tricky thing. Do you know of the butterfly effect? Yeah. But seeing the future can be scary, too.

10. Would you rather work for a boss you hate but make good money or work for a boss that you love but make minimum wage?

We've all thought of this at some point. It sounds like the craziest thing to choose the boss you hate, but life does that to us.

11. Would you rather die in 20 years with no regrets or die in 50 years with no regrets?

Regrets are a big part of life. Maybe we can manage to work with them. This is the right question to see how your friends view regret.

4 Deep Conversation Topics For Your Favorite Persons

We all want a healthy relationship! It's essential to know how your friends view relationships so that you can guide them to the person they can have a meaningful connection with.