40 Questions to Ask Your Best Friend

Best friends are the people you can sit in silence with. They're also the people you've somehow never asked the important questions. Fix that tonight.

The nostalgic ones

1. What's the first thing you remember about me?
2. What's a memory you have of us that I probably don't?
3. What were you most afraid of when we first met?
4. What's the version of me that you miss?
5. What do you think we'll be doing in twenty years?

The honest ones

1. What's a lie you've told that you never got caught for?
2. What's the nicest thing anyone's ever done for you?
3. What's something you're jealous of — and not proud of it?
4. When did you last feel truly lonely?
5. What do you wish someone had told you at 18?

The friendship ones

1. What's the kindest thing I've ever done for you?
2. When have I let you down?
3. What's something you've never told me about us?
4. What's your favourite of my terrible habits?
5. Would you trust me with a secret you've never told anyone?

The fun ones

1. If we had to swap lives for a week, what's the first thing I'd get wrong?
2. What's a skill you have that I don't know about?
3. If we started a band tomorrow, what's our name?
4. What's the most embarrassing thing you've done in front of me?
5. What's our "thing" that nobody else gets?

Make it last

Turn the answers into a keepsake. A Best Friend experience with your photos, your inside jokes and the story of how you met is the kind of gift they'll actually re-open.

Great friendships aren't measured in years. They're measured in conversations you finally had.

Start with question one. Tonight.