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Have you ever given a gift that the recipient hated (or didn’t know what to do with)?ġ2. If you had to get a tattoo, what would you get and where would it go?ġ1. If you could have dessert every day, but it had to be same thing (every day), what would it be?ġ0. If you could eat one thing for dinner every day, what would it be?ĩ. What’s one thing about you that you’d never mention on a first date?Ĩ. What do you do when no one else is around that you’d rather most people didn’t know about?ħ. If you could play a friendly prank on any actor, whom would you prank and how?Ħ. If you could go on a date – or just out to dinner - with a celebrity, who would it be?ĥ. If you had to choose between living in a fully modernized castle (air conditioning, adequate heating, plumbing, wifi, etc.) by a waterfront and living in a spacious, light-filled, and beautifully furnished downtown apartment, so you could walk everywhere, which would you choose?Ĥ. If you could wake up with a completely different permanent hair color - any color - what would it be?ģ. If you could earn any amount as your monthly income, what would that be and why? Funny Questions to Ask Your Best FriendĬhoose from any of these 25 fun questions to ask your friends :ġ. What relationship shaped you the most when you were growing up?Ģ5. What book has had the biggest impact on you?Ģ3. If you could travel to anywhere in the world, and money was no object, tell me where you’d go and how you’d get there.Ģ2. What family member do you feel closest to?Ģ1. What is your biggest challenge right now (and is there anything I can do to help)?Ģ0. What are you most proud of? Or when did you last feel overwhelmed with pride in yourself or in someone else?ġ9. If your next home could have one thing of your choice that your current home does not have, what would that thing be?ġ8. Where do you hope to be three to five years from now? How about ten years?ġ7. If you could be close friends with any celebrity, who would it be?ġ6. If money were no object, what one thing would you buy for yourself to make life easier or more fun?ġ5. Who was the last person to make you cry? What do you wish this person would have said to you?ġ4. If you won half a billion dollars from the lottery (assume you bought a ticket), what would you do first?ġ3. If someone you cared about voted for a candidate you strongly dislike, would you forgive that person?ġ2. What do you believe will happen to you when you die?ġ1. When you’re sad or upset about something, how do you like to be comforted? Or would you rather be left alone to process it?ġ0. Do you ever wish you’d handled a situation differently? How do you wish you’d handled it?Ĩ. What challenges do you most want to overcome?Ħ. What do you see in yourself that you admire when you see it in other people?ĥ. What do you see in yourself that you dislike when you see it in other people?Ĥ. What do you most want to accomplish in your life?ģ. Whom do you look up to the most - and what qualities in that person do you want to see in yourself?Ģ. Pick from any of these 25 personal deep questions to ask your friend:ġ. 175 Questions to Ask Your Best Friend Deep Questions to Ask Your Best Friend

You probably have some idea as to the conversation territory your best friend would rather avoid, but you can still learn plenty about each other with the questions that follow. Besties have certain privileges when it comes to getting personal.

This isn’t a first date, after all, and you didn’t just meet your BFF in an elevator. If you look at your best friend sometimes and think, “Do you really know me that well?” or “What do I not know about you that I should?” it can’t hurt to ask some personal questions.