200 Interesting Questions To Ask Friends

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So you’re spending time with friends. You feel like you know them like the back of your hand. Well, how about we spice the conversation up a little?! Here’s 200 interesting questions to ask friends – for entertaining chats and a GUARANTEE that you’ll learn something new!

See, romantic relationships aren’t everything. Friendships are just as valuable too. So keep getting to know your besties, with our top 200 questions to ask friends…

200 Interesting Questions To Ask Friends

So we have a pretty mighty list of 200 interesting questions to ask friends! 

These are written in no particular order, so have a read through, see which ones take your fancy, start conversations and let them escalate into more depth / other topics from there.

There’s no set way to go about it. This post is just here to fill you with inspiration! 

Sound like fun? Then let’s get stuck in shall we…

Interesting Questions To Ask Friends

The best thing about friendships – is that you should be able to say whatever you really feel, without being judged.

Many of their answers, you may also be able to relate to – which only builds on your friendship further. (Cute, I know!)

1) What personality trait do you like most about yourself?

2) What personality trait do you like least about yourself?

3) Are you doing anything to try to work on that / those negative traits?

4) Do you think a person can truly change their ways? Why / why not?

5) Do you think a person should have to?  I mean – is it striving for perfection or aiming to be the best version of yourself? (Let’s discuss!)

6) What physical feature do you like most about yourself? And why?

7) What physical feature do you like least about yourself? And why?

8) What physical insecurities do you think are the most common? And can you relate?

9) What personality trait do you find most attractive in a person?

10) And what personality trait do you find least attractive in a person?

Let’s Keep Them Coming…

11) What would you say is your “type”? What kind of person do you typically go for?

12) Do you think you go for the right or wrong kind of people? And why?

13) Would you ever go for someone significantly different to your type? Why / why not?

14) What’s your opinion on having a “type” anyway? Is it a good or bad thing?

15) We’re friends (of course!), but how do you think your friends are similar to you?

16) In what ways do you think that you’re different to your friends?

17) What’s the most important thing to you when it comes to friendships?

18) What do you think makes someone a “good” friend?

19) How do you think you could be a better friend?

20) What do you wish you spent more time, us doing, as friends?

21) Have you had more positive or negative experiences with friends?

22) Do you find it difficult to trust friends?

23) Do you find it difficult to trust in romantic relationships?

24) What do you like most about being in a relationship?

25) What do you like least about being in a relationship?

Interesting Things To Talk About With Friends

26) Have you had more positive or negative experiences in relationships?

27) What moments / memories will you always remember with an ex? (For good or for bad!)

28) What things do you look forward to the most about future relationships?

29) How close are you with your parents? And why do you think you are / aren’t this close?

30) In what ways are you similar to your parents? Who do you take after more?

31) In what ways are you different to your parents? And how do you think that came about?

32) What do you think are the main things that have shaped you into who you are now?

33) What mistakes have you made, but learnt from, that you can look back on and feel proud about?

34) How close are you with your siblings / outer family? And again, why do you think you are / aren’t this close?

35) Do you ever wish that you had a bigger / smaller family? Why and how?

36) What memories will you always treasure with your family?

37) How important is it that you have children / your own family in the future?

38) What kind of parent do you think you would be?

There’s Some Pretty Interesting Questions Here, Huh?!

39) Are there any things you wish you could talk to your family about? Why do you feel like you can’t?

40) What do you appreciate the most about the people that you have in your life?

41) Do you think that there’s anything missing in your life right now?

42) What simple things make you happy?

43) What do you enjoy doing? How would you best spend your free time?

44) Are there any hobbies you wish you’d pursued when you were younger? And would you ever give them a go now?

45) What were you like when you were younger? And what’s stayed the same / changed to how / who you are now?

46) What’s been your biggest life lesson so far?

47) Is there any advice you wish you could give to your younger self?

48) What’s your biggest fear? (And let’s not all just say spiders… we want something a little more raw than that!)

49) What’s one thing that most people don’t know about you? (Big or small!)

50) Who’s your greatest role model? And why?

Interesting Questions To Ask Friends

Interesting Conversation Starters

51) What morals do you try to live your life by? And how hard are these to stick with?

52) What standards do you set for others?

53) What standards do you set for yourself? 

54) Do you think you have high expectations for yourself / others? Why / why not?

55) Do you find that you get hurt easily, or are pretty resilient?

56) What kind of things hurt you the most?

57) How high would you rate your confidence on a scale of 1-10?

58) What makes you feel most confidence? (Click here for a quick confidence boost!)

59) What things have knocked your confidence in the past?

60) How do your friends / family make you feel about yourself? (Discuss further!)

61) What impact do you think that social media has on you, personally?

62) What’s your thoughts on social media as a whole? Does it do more harm or good?

Now That’s One To Get You Thinking, Right?!

63) What would make the world a better place?

64) What injustices trouble you the most?

65) If you could donate 1 million to a charity, which charity would you choose and why?

66) What social issues do you wish you could change? And how would you go about changing them?

67) What would you do differently if you were running the country?!

68) What are you most passionate about?

69) Do you find it difficult or easy to speak up about the things that are important to you?

70) Do you find it difficult or easy to disagree with someone?

71) What things / types of people do you find intimidating and why?

72) What gives you courage / strength in difficult situations?

73) How do you stay motivated, in work, fitness, or just life? What do you do?

74) How hard would you say that you work? What’s your work ethic like, and why?

75) What lifestyle aspirations do you have? What kind of life do you want to live?

Interesting Questions To Ask Friends

76) What are three things you really want to achieve in life? And why is this important to you?

77) How confident are you that you will achieve your goals?

78) What could stand in your way / stop you from achieving your goals?

79) Who inspires you to achieve your goals?

80) What are your proudest achievements to date?

81) When you where younger, what did you want to be when you grew up?

82) Did you ever expect to do what you do now for work? And do you think you’ll do it for the rest of your life?

83) What is your favourite thing about your career?

84) And your least favourite thing about your career?

85) What’s the best book you’ve ever read?

86) What types or books do you like to read? And why?

87) How about your favourite types of tv shows? And why?

88) Do you cry easily at movies? Which one gets you the most?

We’re Storming Through These Questions Now!

89) What makes you sad, in general?

90) How do you like to be comforted when you’re upset?

91) What makes you stressed?

92) How do you calm down and relax when you need to?

93) What makes you angry? 

94) How often / easily do you get angry?

95) Do you feel more in control or out of control when it comes to emotions?

96) What types of situations make you feel the most out of control, emotionally?

97) How confident would you say you are as a person?

98) How much do you care about what others think? Why / why not?

99) If you could change one thing form your past, what would it be?

100) If you could guarantee one thing happening in your future, what would it be?

Different conversation starters

We’re Half Way Through!

We’ve reached 100 of our 200 interesting questions to ask friends!

How are you getting on? How many of these things did you already know the answers to, or had spoken about before? And how many of these answers surprised you?

Have you found it difficult to answer the questions yourself? And open up?

Because this in itself is good practice… Start by allowing yourself to be more open and expressive with your friends, and you then build the trust up to do it in romantic relationships too.

Anyway – you having fun? I hope to! Then let’s keep them coming…

Interesting Questions To Ask Friends

101) Let’s say you had to pack up and move to another country tomorrow – where would you go?

102) Have you ever thought about living abroad? What do you think would be the best and worst things about it?

103) What have been some of your best travel experiences to date?

104) What are three things that are top of your “bucket list” right now?

105) How many people do you think actually complete their bucket list? And does it matter?

106) What’s one thing you want to do – that you think not many people would want to?

107) If you won the lottery, what would you do with the money?

108) If you could have dinner with anyone dead or alive, who would it be?

109) Are there any conspiracy theories you actually believe in?

110) Do you believe in aliens? Why / why not?

111) Do you believe in ghosts? Why / why not?

112) Do you believe in fate? Why / why not?

Let’s Keep Them Coming…

113) What’s your thoughts on star signs and their significance / meaning? Horoscopes too?

114) Do you believe in soul mates? Why / Why not?

115) What about love at first sight? Is that possible / a thing?

116) In what ways are you different when you’re by yourself vs around other people?

117) Are you different when you’re around friends vs strangers? If so, how and why?

118) Are there any quirks that you have, that you think make you different? (Your friends may have their own opinions on this one too!)

119) Are there any things that you think people probably misunderstand about you?

120) Do you follow your heart or your head more? And which do you think is wisest?

121) What’s your love language? How do you like to give and receive love?

122) Who is the first person you text when you get good news? Or bad news?

123) Who is the last person who made you cry and why?

124) Do you journal? Have you ever? And why / why not?

125) Do you consider yourself a religious or spiritual person?

Interesting Things To Talk About With Friends

126) What does happiness mean to you? And how do you think you get it?

127) What does success mean to you?

128) How much do you think about / value your health?

129) Would you ever try to run a marathon? Or take on an extreme challenge?

130) What’s the most daring thing you’ve ever done?! (Think adrenaline experiences!)

131) Would you rather see five years into the future or 20 years into the future?

132) If you could travel back in time to any historical event, which would it be and why?

133) Let’s say you could trade places for someone for the day, who would you choose and why?

134) If you could change your name, what would you change it to?

135) What does your name mean, and why was it given to you?

136) Do you like your partners name? (If relevant.) Come on, be honest!

137) Have you ever been bullied? Or ever bullied someone else? (To any degree.)

There’s Some Different Ones In Here, Hey?

138) Do you get on with your work colleagues? What do you think of them?

139) What’s the best present you’ve ever received? And what made it so special?

140) What’s the worst you’ve ever been physically hurt? And how did it happen?

141) What’s your earliest childhood memory?

142) What’s been the hardest goodbye in your life so far?

143) When it comes to comfort foods – what’s your go-to? Both sweet and savoury?

144) On that note – what are your favourite sweet and savoury foods?

145) What’s the best compliment you’ve ever received? And what made it stick with you?

146) Do you have any hidden talents that I don’t know about? Spill, spill, spill!

147) When was the last time you were jealous? And what over?

148) Do you find it hard to let go of things? And hold grudges? Or not?

149) What’s the worst decision you’ve ever made?

150) What things do you think are unforgivable? 

Interesting questions to ask

Interesting Conversation Starters

151) Who was your first best friend and are they still in your life?

152) Do you speak to many of the people you went to school with, or know how they’re getting on?

153) Have you ever had a “friendship breakup?” What was it over? And what did it teach you?

154) Have you ever had a big fall-out with a family member? Again, what was it over? And did you make up? If so, how?

155) What do you think is the best way to resolve conflict?

156) How strong do you think your communication skills are?

157) What does a healthy relationship look like to you?

158) How did your parents meet? What was their little “love story?”

159) What’s your views on divorce? And if your parents are divorced, how did it affect you?

160) What’s the worst date you’ve ever been on?

161) Who is / has been your most embarrassing crush?!

162) What would your dream date be like?

163) What would your dream home look like?

164) Which chore do you dread doing the most?

165) If you could master a foreign language in a day, which one would you choose?

166) What’s your favourite way to exercise?

167) Talk me through your skincare routine! What do you do and when?

168) Are you afraid of ageing? Why / why not?

There’s Some Big One’s Coming Up Now Then…

169) Are you afraid of dying?

170) What do you think happens when we die? (Sorry, this one’s perhaps a little morbid!)

171) Do you feel that you’re young at heart, or an old soul?

172) If you could be born in any other era (or choose this one) which would you choose and why?

173) What’s one thing that’s happened to you that you never expected would?

174) What embarrasses you the most / has been your most embarrassing moment to date?

175) What things do you think aren’t spoken about enough in society? And why?

Interesting Questions To Ask Friends

176) What things would you like to do, but are too scared to?

177) What do you think is the best way to overcome a fear? And can you overcome any?

178) Do you have any phobias?

179) What are your biggest pet peeves and why?

180) How do you feel about alone-time? Like it? Dislike it? And how much do you need?

181) How do you feel when you’re the centre of attention?

182) Do you think you get sick often? And how do you handle being poorly?

183) How much time do you spend thinking about the past?

184) How difficult / easy do you find it to stay present? And why?

185) What do you think you’ll be like when you’re old?

186) How mature do you think you are, and what key life lessons do you think you are yet to learn?

187) Describe your dream retirement! How would you spend your time?

We’re Into The Final Set of Interesting Questions Now…

188) What would you do if you found out you only had one week left to live?

189) If you were going to be famous for one thing, what would you most like to be famous for?

190) What do you think is the best way to deal with regrets? How do you let go of them?

191) What’s the toughest decision you’ve ever had to make? And do you think it was the right thing?

192) What moments in your life have you laughed the hardest? And who makes you laugh the most?

193) If you had to describe yourself in just three words, which words would you choose?

194) If you had to describe ME in three words, which words would you choose?!

195) What do you like most about me, as a person?

196) Why do you think we get on so well? In what ways are we similar / compatible as friends?

197) How could I be a better friend to you? (Come on, be honest!)

198) How many friends are too many? And is there such a thing?

199) What’s your favourite thing to do with friends? Or what would be your idea of the best thing(s) to do with friends? (Click here for ideas!)

200) Shall we make a friends-date bucket list? What things would you like to add on?!

200 Interesting Questions To Ask Friends

So there we have it! We’ve reached the mighty 200, when it comes to interesting questions to ask friends. (Woohoo!)

You should be bursting with inspiration for conversation now. Uh huh, no more girls nights that are “samey!”

So, have fun. Be sure to SAVE this article for future reference. And use it however you please.

Looking for something a little wilder? Then check out these 100 Fun Dares For Your Friends.

These are usually paired with these juicy questions to ask your friends, for a fun game of truth and dare. But you decide how to best use them.

Whatever you choose – have fun, always!

All the best.


Interesting Questions To Ask Friends
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Ella Stearn
Ell is a Breakup, Dating & Relationship Specialist & Coach, with over 3 million annual readers, globally. As the Creator of Forgetting Fairytales, her mission is to help you learn to love yourself, find the right person to give your love to, then make it a love that truly lasts.

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