15 Uncomfortable (But Healthy) Questions to Ask Your Best Friend

November 20 | By ESPA Jewelry

Friendships are built on trust, shared experiences, and genuine connection. But how often do we truly dig deep and ask the questions that matter?

How often do we fall into the trap of small talk, even with those we truly trust?

Uncomfortable questions can feel risky, but they often lead to the most profound conversations.

If you’re ready to take your friendship to the next level, here are 15 questions that challenge comfort zones and deepen relationships.

15 Deep Questions to Ask Your Best Friend

These questions are specifically designed to get to the core of your friendship: how you treat each other.

They can be asked in any order: but we find they're best asked in order!

1. What’s something you’ve always wanted to tell me but never have?

We all have thoughts we hesitate to share, even with those closest to us. This question opens the door for your friend to express something they may have been holding back, whether it’s a compliment, concern, or even an untold story. The results can be surprising and heartwarming.

2. Do you feel supported by me in our friendship?

Friendship is a two-way street, and asking this question shows you value their perspective. They might share areas where they feel uplifted or areas where they could use more support, giving you a chance to strengthen your role in their life.

3. What’s one thing I do that annoys you?

Every friendship has its quirks, and sometimes those quirks can irritate us without us even realizing it. This question helps clear the air and can lead to self-awareness and growth. Plus, it might give you both a reason to laugh at the little things that make your relationship unique.

4. What’s one thing I do that annoys you?

Misunderstandings happen in every relationship, and we’re not always aware of the impact our words or actions might have. Asking this question shows humility and a willingness to address any unresolved feelings, strengthening the trust between you.

5. What do you think is my biggest flaw?

Hearing constructive criticism from someone who loves you can be hard, but it’s often the most helpful. This question gives your friend an opportunity to share insights you might not see in yourself, offering a path for personal growth.

6. Do you feel like I’m a good listener?

Listening is an underrated skill, and sometimes we think we’re attentive when we might not be. This question lets your friend reflect on whether they feel truly heard during your conversations, and it encourages you to be more present if needed.

7. Is there something about yourself you wish more people understood?

This question allows your friend to open up about a side of themselves they might feel isn’t seen or appreciated. It’s a chance for them to share their struggles or unique traits, creating deeper empathy and connection between you.

8. What’s the hardest thing you’re dealing with right now?

9. What’s something you’re scared to pursue but really want to?

We all have dreams and fears, and this question creates a safe space for your friend to explore theirs. You might be able to encourage them or even offer practical advice to help them take that next step toward their goals.

10. What do you admire most about yourself?

This question flips the script from self-criticism to self-love, giving your friend a chance to celebrate their strengths. It’s a reminder that self-acknowledgment is important, and hearing their answer can be both inspiring and insightful.

11. Have you ever felt jealous of me?

Jealousy is a natural emotion, even in the healthiest friendships, and acknowledging it can actually help to diffuse it. This question encourages honesty and can lead to a meaningful conversation about how to support and celebrate each other better.

11. Have you ever felt jealous of me?

Even the strongest friendships have room for growth. This question invites collaboration and shows your commitment to making your relationship as fulfilling as possible for both of you.

13. What’s a boundary you wish I understood better?

Boundaries are vital for any healthy relationship, and this question encourages your friend to share theirs openly. It shows respect for their needs and a willingness to adjust to ensure mutual comfort.

14. What’s one memory of us that stands out to you?

Reflecting on shared memories is a great way to rekindle joy and appreciation for your friendship. Whether it’s a funny story, an emotional moment, or a milestone you’ve reached together, this question highlights the value of your bond.

15. How can I show you love and appreciation better?

We all have different ways of feeling loved, and understanding your friend’s preferences can take your relationship to a new level. Whether it’s through kind words, thoughtful gestures, or quality time, this question helps you align with what matters most to them.

Why These Questions Matter

Asking these questions might feel a little uncomfortable, but that’s the point—stepping outside your comfort zone creates space for growth and connection. Friendships that can tackle tough conversations tend to be the ones that last, offering both emotional depth and mutual support.

After diving into these meaningful discussions, why not celebrate your bond with a thoughtful gesture?

The Unending Love ESPA Necklace is a perfect symbol of a friendship that knows no limits. It’s more than just a piece of jewelry; it’s a lasting reminder of the connection you’ve built and the love you share.

So if you want to show your bestie in “More Than Words,” check out the Unending Love ESPA Necklace Here to find the perfect way to honor your friendship.