20 Things To Ask Your Best Friend To Make Your Relationship Even Stronger

On a recent road trip with my best friend, I came to a surprising realization. Though we've known each other for years, though we live together, though we spend all day texting and all night gabbing, there's still plenty we don't know about each other. Somewhere in the midst of constant interaction and communication, we failed to connect all the dots.

Whilst stuck in traffic somewhere along the thruway, we cycled through our usual topics: social gossip, celebrity rumors, family drama, relationship woes, financial stress, commentary on the news, 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.

And what started out as a few failed attempts to guess Hilary Clinton and a hair elastic, we 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. So without further adieu, here are 20 questions to ask your best friend that will make your relationship stronger than ever.

What would you like to make time for?

Giphy

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

What are you scared of?

Giphy

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

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

Giphy

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

What's on your bucket list?

Giphy

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

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

Giphy

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?

Giphy

Note to self: things not to do!

What have you always wanted to try?

Giphy

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?

Giphy

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

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

Giphy

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?

Giphy

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

What's your favorite viral video?

Giphy

Yes, if you could only pick one, what would it be? The Hamster Dance? The snacking sloth?

What song gets you going?

Giphy

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?

Giphy

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?

Giphy

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?

Giphy

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

Who understands you the best in your family?

Giphy

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?

Giphy

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?

Giphy

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?

Giphy

It's a tasteful way of breeching the "God" question. Judgement free.

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

Giphy

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

Images: Pixabay, Giphy (20)