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Do You REALLY Know Them? 20 Fun Questions to Ask a Friend

questions to ask a friend

How well do you know your friends? Sure, you know them, but how deep does that go? Here are 20 important questions to ask a friend.

We all think we know our friends, but how many of us have sat down with a bottle of wine and asked some thought-provoking questions? Not many. If you want to become better friends, the best way to do it is to actually get to know them.

Friendship isn’t only based on having someone to go shopping with or someone to talk to about your new crush. I mean, these are all a part of it, but that’s just the surface. So, if you want to go into deep waters, get the conversation going by asking some interesting questions.

20 questions to ask a friend and get to know them better

You’ll be surprised by how much you’ll learn about your friend. It’s amazing how many of us never think to ask these.

#1 Who was the first person you had a crush on? Who said these questions had to be serious? Also, everyone remembers their first crush. Everyone. It’s like knowing your phone number – impossible to forget. This question is a fun way to take you and your friend down memory lane. My first crush was Trevor Samson – he is now a metal head who has a snake fetish. Oh, how things change.

#2 What is one thing you regret doing or not doing in your life? This is one of the most powerful questions to ask a friend. Was it that you never asked out that girl you really liked? Or bailed out of a skydiving trip because you were scared? Maybe because of this question, you and your friend will try doing things that you were scared to do before. [Read: How to make REAL friends outside your social networks]

#3 What is your most embarrassing moment? It’s always funny to hear the answer to this question – until you have to answer it yourself. Did you fart on a crowded subway? Or did your friend accidentally flash a group of people? We all have embarrassing moments. I have an unusual amount, but the good thing is that they make for a funny story later in life. And a cringe. A strong cringe.

#4 What’s your dream job? This is one of the standard questions to ask a friend. Doctor? Actress? Teacher? What’s your friend’s dream job? What’s YOUR dream job? And why aren’t you two working your dreams jobs right now? Maybe with each other’s help, you can actually achieve your dream jobs. Unless it’s an astronaut, I mean, it’s still possible – but a solid challenge.

#5 If you could travel anywhere in the world, where would you go? Where in the world would your friend go if they had the opportunity? Maybe you could go together to that destination. Is it India? Australia? Mexico? Maybe this question will inspire a crazy traveling adventure.

#6 What are you afraid of? Fears are huge and everyone has them. It’s what makes people not go out and try things that they’re curious about. What are your friend’s fears? What keeps them from sleeping at night? Hopefully, it’s as small as being scared of snakes or spiders. But for some, it’s larger than that, and as a friend, you should find out. [Read: 17 bad friends that you should unfriend from your life]

#7 What’s one of your favorite memories? This question may even bring some tears to the eyes. Maybe it’s when your dad was teaching you how to ride a bike or when you were baking cookies with your grandma. These memories are what makes us feel warm and wholesome. It’s a great question to ask a friend.

#8 Which family member are you closest to? I’m closest to both of my parents, but for some, it’s their aunt or great-uncle. What makes this person the one you confide in? And don’t say it’s because they give you money for your birthday.

#9  What is your biggest insecurity? Oh Lord – we all have our insecurities! Maybe your friend is insecure about her smile or the scar on her arm from falling off her bike. The list of insecurities that people have can turn into a scroll. It’s important to know your friends’ insecurities because you’ll want to discover them – just in case you’ve been teasing them about it this whole time *and then stop*.

#10  What do you love about yourself the most? Ahh, it’s a beautiful thing when you see someone show you what they love about themselves because it’s probably what you love about them as well. I love my inability to hold in my gas. I’m kidding. It’s a living nightmare.

#11 What have you always wanted to try? This question is great for getting you two off the couch and crossing something off of your bucket list. River rafting? Bungee jumping? Whatever it is, you two have to try it together. [Read: How to be good friends with a co-worker]

#12 If you could go back in time, what year would you travel to? When you ask this question, you’ll open up a part of them that maybe you haven’t seen before. Maybe they’ll pick a Victorian period. Why? Or they’ll choose sometime in the 80s. But why?! This question, though it may look silly, can you show you a lot.

#13 If you had $10,000 to spend today, how would you spend it? Ahh, yes. Here we go again. Another great question to ask a friend. What would any of us do with $10,000? Spend it on clothes? Shoes? Video gaming equipment? What would you do with this chunk of cash?

#14 If you could invite anyone to dinner, living or dead, who would it be? Take a look at who they would have at their dinner table if they had the choice. Maybe it would be a celebrity or politician, or maybe it would be a loved one who has passed away. It’s always interesting to see people’s choices on this one. Mine would be my grandpa and Ryan Reynolds. I picked Ryan only because he’s cute. Yeah, I know it’s superficial. But maybe, just maybe, I have a chance. [Read: Are you losing your friend or just drifting away?]

#15 If you could live anywhere in the world for one year, where would it be? Ooooh, I think this is maybe one of my favorite questions to ask a friend. Because it always ends up with me and my friend Googling destinations and rental properties.

#16 Who has influenced you the most? Now, this one is a deep question. Who changed the life of your friend? Who inspired them to be who they are today? Maybe it’s someone you know personally, or maybe not. But, it’s always interesting to see why your friend does the things they do.

#17  What three words would you use to describe yourself? Oh! Oh! Oh! I love this question because my friends give me descriptions that are completely the opposite of what they are. I’m usually left thinking, “well, you’re not really that funny.” This question is a good one to see how your friend views him/herself and how you view yourself. [Read: Bad friends and when to end a friendship]

#18 What would you eat for your last meal? Is it pizza? Mine would totally be pizza. Or calamari. Or pasta. Or steak. Wait, there’s just too many options. Or maybe it would be a fruit salad. I don’t know.

#19 What would be your perfect day? On the beach with a cute guy who rubs suntan lotion on your back? Playing video games with your best friends without your mother yelling at you? [Read: Do you think alike? 20 questions to ask your best friend]

#20 What happens when you die? Of all the questions to ask a friend, this one is probably as deep and personal as it gets. And since this is not the lightest lightest question to ask, you can either ask this one in the beginning or end. I know you’re probably thinking, “Why is this a good question?” But it could spark up a healthy debate. Is it reincarnation? Heaven? Nothing?

[Read: The 8 types of friends everyone needs in their life]

If you want to get to know your friend better, these 20 questions to ask a friend can be made into a fun game. If nothing else, they will get the conversation going. And who knows what you’ll find out?

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Natasha Ivanovic
Natasha Ivanovic
A serial dater, Natasha Ivanovic knows a thing or two about men and the dating scene. Much of her writing is inspired by her encounters with men - and for good ...
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