20 Questions That Help Strengthen Your Friendships

by Kaitlyn Wylde
Originally Published: 
Gossip Girl

On a recent road trip with my best friend, I came to a surprising realization: we've known each other for years, we live together, we spend all day texting and all night gabbing, and yet there's still plenty we don't know about each other. Somewhere in the midst of constant interaction and communication, we have failed to connect all the dots. There are things you can ask your best friend that will make your bond stronger — for instance, though I know that my best friend likes to watch old episodes of Seinfeld when she's sad, I don't know the right things to stay after she gets in a fight with her mom or gets rejected from a job she applied for. It occurred to me that many adult friendships, especially between roommates, can escalate quickly, creating a false sense of intimacy and closeness that takes an extra effort to create something more authentic and honest.

Whilst stuck in traffic somewhere along the thruway, my best friend and I cycled through our usual topics: social gossip, celebrity rumors, family drama, relationship woes, financial stress, and a lot of grunting and moaning regarding the slow pace of traffic. Her phone was dead, I was driving so I had mine tucked away, and we were a good three hours out from our destination. Without the distraction of mindless Instagram scrolling and without the freedom to leave the car, we decided to play a game of 20 questions that changed the way I approach friendships in my adult life.

What started out as a few failed attempts to guess "a corgi" and "The Lion King," we had decided to play a new kind of 20 questions; we asked each other personal questions. And before long, we arrived at our destination, knee-deep in heady, contemplative conversation, leaving us feeling closer than ever and equally fascinated with each other. Which is no easy feat when you spend most of your time with someone. As it turns out, there is something specific I can say to help comfort my best friend after she gets into an argument with her mother, and to my surprise, she'd much rather go get ice cream than hole up with Seinfeld for an afternoon. In those three hours, we got to know each other in a way we might never otherwise had the chance to. So, here are 20 questions to ask your best friend that will make your relationship stronger than ever — and, of course, help to pass the time.

"What would you like to make more time for in your life?"

Talk about what you've meant to fit into your life but haven't been able to.

"What are you scared of?"

Ghosts? Death? Bees? Rejection? Direct questions elicit honest responses.

"When you're upset, do you want space or attention?"

You might find out that all this time you've been coddling your friend, she's wanted just a minute alone.

"What's on your bucket list?"

You might unearth some cool adventures for you two to do together.

"What do you struggle with on a day-to-day basis?"

Empathy is a great skill. To understand your friend, you have to understand what it feels like to be your friend.

"What embarrasses you in front of other people?"

Note to self: things not to do!

"What have you always wanted to try?"

Another great opportunity to try something together. Whether it be mushroom pizza or skydiving, it will certainly spark a fun conversation.

"If you had to spend $10,000 today, how would you spend it?"

A great way to learn about each other's priorities and indulgences.

"If you started your own non-profit, what would it be?"

Tap into your generous side and learn about what your friend really cares about.

"What do you like to do first thing in the morning?"

Brush your teeth? Cradle your iPhone? Learn the best way to approach each other in those early hours.

"What's your favorite viral video?"

Yes, if you could only pick one, what would it be? The Hamster Dance? Kristen Bell crying over the sloth?

"What song gets you going?"

We both lowered our heads here and whispered, "What Do You Mean?" by Justin Bieber. The shame was lifted.

"What are you most insecure about?"

This might surprise you how hard it is to answer honestly. But you'll feel better after you do.

"What's the title of your quarter-life autobiography?"

Try naming each other's books. This could go on forever.

"If you had to live in another country alone for a year, where would it be?"

Get creative, broaden your horizons. Encourage each other to consider travel and independence.

"Who understands you the best in your family?"

This might be a tone-changer, but it's good to know each other in the way.

"What relationship do you think needs work in your life?"

Maybe it's not something you think about on the regular, in that case, you might find this question extra stimulating.

"What happens when you die?"

It's not a trick question. There's no wrong answer. No matter what you say, you'll be offering a whole lot of insight into your soul.

"When you're scared, who do does your mind reach out to for safety?"

Judgment free.

"If you could re-do one day in your life, which would it be and why?"

Maybe the answer is that you wouldn't. That's fine too.

There's no "right" answer for any of these questions, they're just designed to inspire you and your friend to open your minds and hearts to some fresh conversations. If one question leads you away from the list, follow it!

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