30 Uncomfortable Questions You Should Ask Your Best Friends

Asking your friends for advice is a great way to get insights into their lives, but sometimes the questions we want to ask are a little too personal. We don't want to seem nosy or intrusive, so we hold back. But if you really want to get to know someone, you need to be willing to ask the tough questions.

In this article, we've compiled a list of 30 uncomfortable questions you should ask your best friends. These questions will help you get to know them better and learn more about their hopes, fears, and dreams. So go ahead and ask away—your friends will appreciate your candor!

Why Do You Need to Ask Uncomfortable Questions?

You might think that uncomfortable questions are best left unasked, but that's not always the case. Sometimes, in order to get to know someone better, you need to go beyond the surface and ask the tough questions.

And that's where uncomfortable questions come in. They can help you understand someone in a deeper way, revealing things you wouldn't have otherwise known. Plus, asking uncomfortable questions can help strengthen your relationship with the person you're asking them of.

So don't be afraid to ask them—you might be surprised at what you learn.

How to Ask Uncomfortable Questions

It can be tough to know what questions to ask your loved ones, especially when you want to get to the bottom of something but don't want to hurt their feelings. But sometimes, you have to bite the bullet and ask the tough questions.

The key is to do it in a way that's respectful and understanding. Start by explaining that you just want to get a better understanding of what's going on, and then ask away. Be prepared for some uncomfortable answers, but remember that it's better to know the truth than to live in a state of ignorance.

And if you're on the receiving end of an uncomfortable question? Try not to take it too personally. Remember, the person asking is just trying to understand what's going on—they're not trying to attack you.

30 Uncomfortable Questions to Ask Your Best Friends

You know your best friends pretty well. But are you sure you know everything about them?

There are some uncomfortable questions that you should ask them, just to make sure. Questions that may make them a little bit uneasy, but that will ultimately help to deepen your friendship.

Questions like: "What are your biggest fears?" or "What's the most embarrassing thing that's ever happened to you?" can be tough to ask, but they're worth it.

When you get answers to these kinds of probing questions, you learn more about your friends and what makes them tick. And that can only lead to a stronger friendship.

What if Your Best Friend Doesn't Want to Answer the Question?

What if your best friend doesn't want to answer the question? What if they get offended?

Well, that's a risk you'll have to take. But hopefully, your friend is comfortable enough with you to know that you won't judge them. And if they're not, then maybe they're not the best friend for you.

This is a time where you need to be honest with yourself. Are you really friends with this person, or are you just acquaintances? Because if it's the latter, then you don't need to have this kind of uncomfortable conversation.

How to Deal With Difficult Conversations

It's inevitable that you'll have to deal with difficult conversations at some point in your life. Maybe you're feeling uncomfortable about something your friend said. Or maybe there's something you need to talk about but you're not sure how to bring it up.

No matter what the situation is, it's important to face these conversations head-on. The key is to approach them with empathy and understanding, and to remember that your goal is to work things out, not to win or "be right."

To help you navigate these tricky waters, we've put together a list of 30 uncomfortable questions that you should ask your best friends. We hope they'll help you get to the bottom of whatever's bothering you, and that they'll pave the way for a more open and honest relationship.

FAQs About Asking Uncomfortable Questions

Questions are a powerful tool, but there are some questions that are just too uncomfortable to ask. Questions about money, sex, and politics come to mind.

But what if I told you that asking the tough questions is actually the best way to build strong relationships? That's because when we ask uncomfortable questions, we're really trying to get to know the other person on a deeper level. We're trying to understand their motivations and what makes them tick.

So how do you go about asking uncomfortable questions? It can be tough, but it's not impossible. Just be prepared for the other person to get defensive or even angry. The key is to be respectful and understand that they may not want to answer certain questions.

If you can master the art of asking uncomfortable questions, you'll be able to build stronger relationships with the people you care about most.


Asking your best friends tough questions is never easy, but it can be a really rewarding experience. You may not always like the answers you get, but they can help you grow as a person.

So don't be afraid to ask the tough questions – your best friends will be happy to answer them.