A List of 20 Important Questions To Ask Your Best Friend

Whether you call them your BFFL, your confidant, your partner in crime, or your platonic soul mate, a best friend is an irreplaceable source of joy and support. They’ve helped you apply your eyeliner on your wedding day, and they’ve dug to the bottom of a Ben & Jerry’s pint with you when a loved one passed away.

A best friend is someone you can always turn to in your moments of triumph as someone to celebrate with and in your moments of darkness so they can pull you back towards the light. But can your relationship go even deeper? To test that theory, here are some thought-provoking questions to ask your best friend.

What Makes Deep Conversations Important

According to some scientific studies, those who engage in deeper conversations with the people around them tended to be significantly happier than those who engaged in mostly small talk.

Psychologist Matthias Mehl and his team studied this concept with students on a college campus. After analyzing and categorizing their conversations, the person who was reportedly the happiest engaged in twice as much substantive conversation as the unhappiest person, while having only one-third of the small talk.

While deeper conversations in general lead to a happier, more fulfilled life, having these conversations with friends gives you the opportunity to connect with those you love on a deeper level.

Friends are not only good for the soul, but for your health as well. Those with friends experience emotional benefits, such as decreased loneliness, and also exhibit a lower chance of experiencing a stroke, heart attack, or diabetes. Positivity comes with a variety of health benefits, so keep friends who keep you calm close.

With these benefits in mind, let’s take a look at a variety of questions to ask your best friend so you can start connecting even more.

Questions To Ask Your Best Friend

The Silly Questions

To get the ball rolling, start with a list of questions that will make you both laugh!

What song always brings you back to your cringy middle school days?
What are your biggest pet peeves and how do you handle your rage when someone performs them around you?
What was the most expired item in your fridge that you’re ashamed to admit you ate?
What’s the most awkward thing your parents have ever said in front of someone?
Who’s the first actor that you ever had a celebrity crush on? And would you still take them up on a date if they asked?

The Favorite Questions

Do you know what your friend loves most? Let’s see if you can guess before they answer!

What’s one of your favorite songs that will never fail to cheer you up when you’re down? What’s a song that you love that will always make you cry?
If you could travel anywhere, where would you go? What is your favorite place in the world?
What’s the TV show you always turn on when you need some comfort?
What’s your favorite memory? And what makes it your favorite?
What’s your favorite adventure we’ve had together? Why was it your favorite, and when can we plan the next one?

The Real Life Questions

What makes your friend tick? Do you know where they’d like their life to be in five years? What happened in their past that made them who they are today?

Even if you hated it, what book has impacted your outlook on life the most?
What is your dream job? The one you would drop everything for and move across the country to start if you were offered it today?
When have you felt the most challenged? When you’re at work, or when you’re on the dating scene?
When was the time you laughed the hardest?
You can teleport and money is no object; what is your perfect day?

The Deep Questions

Time to take it up another level. Let’s get real, y’all!

If you lived the rest of your life exactly as you do now, would you be truly satisfied?
Do you remember a moment in your life that made you question everything?
Do you think someone should ever be able to complete a bucket list? Or should you continuously add to it? And what does your answer say about the way you look at life?
Do you have a “biggest mistake” that you would give anything to fix if there were no repercussions?
Is your biggest fear dying alone or spending your life with someone you don’t love?

Why It All Matters

Asking each other questions to get to know one another better is a lot of fun in the moment, and it will ultimately bring you closer to one of your favorite people.

So in the end, why does it matter whether or not you know your best friend’s favorite brand of mac and cheese?

While it might seem like a trivial fact, imagine how touched you would feel if you texted your friend that you had a rough day and she arrived half an hour later with unicorn-shaped Kraft macaroni and a bottle of rosé?

You’d probably feel valued, seen, heard, and loved. And doesn’t your friend deserve someone who makes them feel like that?

Sarah Margaret Henry

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Author, Artist, Photographer.

Sarah Margaret is an artist who expresses her love for feminism, equality, and justice through a variety of mediums: photography, filmmaking, poetry, illustration, song, acting, and of course, writing.

She owns Still Poetry Photography, a company that showcases her passion for capturing poetic moments in time. Instead of poetry in motion, she captures visual poetry in fractions of a second, making cherished keepsakes of unforgettable moments.

She is the artist behind the Still Poetry Etsy shop, which houses her illustrations and bespoke, handmade items. She is the author of intricacies are just cracks in the wall, a narrative poetry anthology that follows a young woman discovering herself as she emerges from an abusive relationship.