You know almost everything about them (way better than scientists who only know 35% of the earth!)
They know just as much about you too.
While the depth of the friendship can bring a lot of joy according to research, it can also lead to complacency. For example, because you know each other so well, conversations have gone stale now and then.
So how do you inject some energy into your already awesome friendship?
I have close friendships that span 10+ years, and here’s how to start meaningful conversations with your best or close friend:
Discover what you don’t know about them still
Assume that you know less about them than you think. Kate Murphy, the author of You’re Not Listening, said:
“We actually all tend to make assumptions when it comes to those we love. It’s called the closeness-communication bias. As wonderful as intimacy and familiarity are, they make us complacent, leading us to overestimate our ability to read those closest to us.”
To test how much you know about each other, go through the following questions with your best friend:
- Would you rather…
- What do you feel uncomfortable talking about?
- What do you wish more people knew about you?
- What’s something most people don’t understand about you?
- What’s something that I don’t know about you?
- What’s something you haven’t told anyone/me before?
- What’s your biggest secret?
Get them to tell you about their recent changes
As I noted earlier, the closer we are to someone, the harder it can be to notice their learning and growth. Get your best friend to share what’s different/new about them, and be prepared to be surprised!
- What’s the most interesting/surprising/profound thing you learned recently?
- What’s the most interesting/surprising/profound thing you experienced recently?
- What have you changed your mind on recently?
- What did you strongly believe in, but no longer do?
- What didn’t you believe in but do now?
- What’re you trying/exploring these days?
- What would you like to try/explore?
- If you had all the time in the world, what would you like to experience and why? (more lifestyle-related questions here)
- If you could be in any career for a day, what would it be? (more career-related questions here)
- If you didn’t have to worry about anything, what’s the biggest career/life change you’d make?
Talk about controversial/taboo topics
Sometimes, you need a jolt of shock to reignite your best friendship… Some of these questions might just put your friendship to the test, but could be worth a try!
- What’s the dirtiest thing you’ve ever done? (sexual or non-sexual)
- What’s the dirtiest thought you’ve ever had?
- What’s the most evil thought you’ve ever had?
- What important truth do very few people agree with you on? (Credit: Peter Thiel)
- What’s the most controversial thing you believe in?
- If you had to explain the birds and bees to kids/schoolchildren, what would you say?
- If you had to pick one cause to support, would it be feminism or environmentalism?
- What popular cause do you not care about/disagree with?
- Would you kill one person to save five?
- Do you believe in God? Why or why not?
- What if God was real? // What if there was no God?
“Future proof” your friendship
From my experience, here’s why close friendships stagnate and even die…
- You outgrow your best friend, or they outgrow you
- You stop sharing the same interests or values (whatever led to a close friendship in the first place)
- You no longer meet or talk regularly
So how can you “future-proof” the friendship? a) Think through what will lead to an even stronger friendship b) Communicate the intention that you would like to continue nurturing the friendship c) Understand what your best friend values in the relationship. Go through the following questions together:
- How has our friendship evolved over the years?
- How will our friendship evolve in the future?
- What’re we becoming less aligned on and why?
- If we stopped becoming best friends, it would be because of…
- If we stopped keeping in touch, it would be because of…
- What would make our friendship even more meaningful/rewarding?
- Which area of life would you want to grow together in?
- How can I support you to achieve your goals? // How can I support you on your journey of… ?
- What do you hope for our friendship?
In my opinion, here’s an incredibly effective, fun way to strengthen a best friendship: share the same experience!
Create new memories together
By doing things that you both haven’t done before, you might just discover a new side of each other, which freshens up the friendship! It sounds obvious, but when was the last time you did something different/unusual with your best friend? Here’s how to get your friend’s buy-in on new experiences:
- What book would you like us to read together?
- What movie would you like to watch together?
- What cafe/restaurant/bar would you like to visit?
- What event would you like to attend?
- Where would you like to check out on the weekend?
- Where would you like to travel together?
Celebrate the good times
While exploring new things and topics is important, it’s equally key to look back on the friendship and recap the magical moments. Here are some “feel-good” questions to help you and your best friend walk down memory lane:
- How many years have we known each other?
- Where did we first meet?
- What was your first impression of me?
- How did we get closer?
- What was your favorite memory of our friendship?
- What do you most like/appreciate about me?
- What will you always remember about me as a friend?
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