Your best friend has observed you over the time you have been together; due to that, they may have something to say about you as well, but you need to give them a comfortable environment to let it out, and this also means you have to ask the right questions.
There are quite a number of questions to ask your best friend that can deepen your connection with them. In this article, you will get to know 20 of them, so let’s get right into these questions that will leave you smiling heavily!
20 Hilarious Questions To Ask Your Best Friend About Yourself
- What is the most interesting thing I do that you always tag as being weird?
- What is the fun action you took to help me overcome procrastination?
- Can you talk about the annoying things I do that make our relationship fun?
- Can you share the funniest thought that came to your mind about my outfit at first sight?
- What do you like about my smile?
- When do actions or conversations of mine drive you crazy?
- Which of my funny jokes stuck in your memory to date?
- Can you mimic my walking steps exactly?
- What funny story of mine have you shared with someone else?
- Will you say I have issues with the color combination? What is the worst combo I ever did?
- Can you predict the exact time I’ll laugh during a comedy show?
- What hilarious attitude did I display in public that made you feel embarrassed?
- Do I have interests in things that are strange to you?
- What will you say is the most ridiculous experience we’ve had?
- What nickname fits into the fun moments we shared?
- Can you name my favorite meal along with my best chef?
- When I have a new crush, what are my most practiced relationship strategies?
- Can you describe the funniest thing about my facial expression?
- Why does my next adventure seem like a waste of resources to you?
- Which of my adventure experiences made you laugh so hard that you cried?
1. What Is The Most Interesting Thing I Do That You Always Tag As Being Weird?
This is a super interesting way to start a conversation with your best friend. It is a fun question about your unique habits, and it shows how curious you are to know how much your friend knows about you.
After setting the ball rolling with the playful tone of your question, you should expect a funny response to the weird behavior you display that makes you interested.
Synonymous question:
- What’s the weirdest habit of mine that you love?
2. What Is The Fun Action You Took To Help Me Overcome Procrastination?
You can share some motivational strategies that your friend practiced to help you become focused and maintain momentum by asking them this question.
This time around, the idea is not just to talk about having a plan and working towards it but a helpful, funny tip that has proven to be super helpful to you.
It will also give anyone who listens to you an idea of how supportive and encouraging your friend is to you.
Synonymous question:
- Which ridiculous way do you keep me motivated?
3. Can You Talk About The Annoying Things I Do That Make Our Relationship Fun?
Every partner in a relationship has something to say about annoying habits that are sometimes fun, and that is what this question is all about.
The question is a playful one that focuses on sharing the ridiculous things you do with your friend that add fun to your relationship, even though they find it annoying sometimes.
Synonymous question:
- What’s the most annoying thing I do that you find funny?
4. Can You Share The Funniest Thought That Came To Your Mind About My Outfit at First Sight?
It will be so interesting to ask your best friend about the funny thoughts they have in mind concerning your outfit. The intention is for them to playfully criticise your fashion style.
Asking them to share their initial amusing reactions to your outfit sounds like a joking question, but you should get set to hear a relatable story that will make you enjoy fun moments.
Synonymous question:
- What’s the first hilarious thing you noticed about my style?
5. What Do You Like About My Smile?
This is a genuine question to your best friend that gives you flattering praise about what makes your smile special. It is exclusively about giving you a ridiculous positive reason why they admire the way you smile.
Beyond the fun that the question brings, it spreads positivity and gives your best friend the opportunity to say what they appreciate about your smile, even as their response ignites so much fun.
Synonymous question:
- Why do you love my smile?
6. When Do Actions Or Conversations Of Mine Drive You Crazy?
Particularly, this question mirrors how people vent frustration. It is playfully asking your best friend to share the actions of yours that got them really annoyed, but this time in a funny way.
Anyway, it is a conversation that you can relate to, but since it is coming from your friend and the intention is to have fun, you can ask them more questions about why your actions drive them crazy as the laughter continues.
Synonymous question:
- What’s the one thing I do that drives you nuts?
7. Which Of My Funny Jokes is Stuck In Your Memory To Date?
In a bid to really joke with your best friend, you can ask them to share the ones they remember. When you want to strengthen the bond between you and your friend, this question is superb.
It gets more fun when they share a funny, memorable joke that you hardly remember or thought they found funny at the time you said it to them.
This is exactly the nostalgic picture that your amusing question tends to paint.
Synonymous question:
- What’s the funniest joke I’ve ever told you?
8. Can You Mimic My Walk Steps Exactly?
There are different ways in which your best friend can decide to tease you. When they do it affectionately, it can be more fun and interesting at the same time.
This is one of the reasons why you should ask your friend to show how familiar they are with you by describing the way you walk.
It will also reveal to you how much they have observed you during the time you have been together with them.
Synonymous question:
- Can you walk like me?
9. What Funny Story Of Mine Have You Shared With Someone Else?
Funny stories about you can be the subject of your question to your friend. You can ask them what fun story about you they shared with someone at any point in time, which can be during a conversation or when describing something you did or said.
It is basically asking them to share with you the stories of you that they use to entertain others.
Synonymous question:
- What’s the best funny story you’ve shared about me?
10. Will You Say I Have Issues With Colour Combination? What Is The Worst Combo I Ever Did?
This is a typical roast on your fashion sense, but since you gave your best friend the platform and opportunity to tease you, prepare to laugh as you anticipate their response.
It is more of a humorous criticism that is super playful because it is about your most questionable outfit combination.
Synonymous question:
- Do I have a weird sense of style?
11. Can You Predict The Exact Time I’ll Laugh During A Comedy Show?
When your best friend can predict your laughter, particularly if you’re often selective about your laughter, it may mean they are so close to you.
The question also reveals their familiarity with you, but this time around, it is based on accurate prediction or understanding your humor preferences.
Synonymous question:
- Can you anticipate my laughter?
12. What Hilarious Attitude Did I Display In Public That Made You Feel Embarrassed?
You may not have an incline that you have done something embarrassing to your best friend until you ask them this question.
This can be the best time to ask them about it in a ridiculous way. When asking this question, ensure that your mood is amusing to afford them the opportunity to share a playful embarrassment.
Synonymous question:
- What’s the most embarrassing thing I’ve done in public?
13. Do I Have Interests In Things That Are Strange To You?
A question to your best friend about your interests that sounds unconventional can be the next best thing you can think of after your relationship with them.
The question gives them an idea of how interested you are in how much they have adjusted to accept you and show you love despite your unique hobbies.
Synonymous question:
- Do I have weird hobbies?
14. What Will You Say Is The Most Ridiculous Experience We’ve Had?
Another thrilling question you should try is to ask your friend about your ridiculous experience. It is an engaging question that will make you laugh at the absurd questions they will recall.
You will definitely get an engaging story about the entertaining moments your best friend will share that will spark the fun in your conversation.
Synonymous question:
- What’s our craziest memory together?
15. What Nickname Fits Into The Fun Moments We Shared?
There are nicknames for fun moments, and if you haven’t had a conversation around it before, this is the right opportunity to do so.
Simply ask your friend to create a special nickname that will summarise the fun moments you’ve had together. If need be, tell them to be playful and affectionate.
You can play around with the names by recalling the moments that inspired them.
Synonymous question:
- What’s my fun nickname?
16. Can You Name My Favourite Meal Along With My Best Chef?
You can ask your best friend to talk about your personal preferences, particularly your favorite meal and best chef.
This will give you insight into how interested your friend is in the things you like and enjoy, including your enthusiasm for a certain meal. You can ask them about your favorite recipe and your most preferred posture when eating.
Synonymous question:
- What’s my favorite food?
17. When I Have A New Crush, What Are My Most Practiced Relationship Strategies?
Typically, your best friend should have observed you and your relationship with the opposite gender if you share those experiences with them.
If you have never given them an opportunity to make their input or you have always wanted to know their thoughts about you in that regard, this is one of the best questions to ask them.
It will introduce some fun, and at the same time, you’ll get to know some helpful relationship strategies from them.
Synonymous question:
- How do I flirt?
18. Can You Describe The Funniest Thing About My Facial Expressions?
Not all questions can evoke super funny responses, but if you often find descriptions funny, then you should ask your best friend this question.
It will give you an idea of the playful way your friend sees you after observing your facial expression, or better yet, your facial features.
Much more, it is a playful way to ask your friend to tease you with affection.
Synonymous question:
- What’s fun about my face?
19. Why Does My Next Adventure Seem Like A Waste Of Resources To You?
Your best friend is one of those people who will get ideas for your next moves, including your plans for an adventure.
If you feel they have not discussed something they have in mind with you concerning your upcoming travel plans, this is a suitable question to ask them, with emphasis on a curious and playful tone. You should expect an exciting response.
Synonymous question:
- Where’s my next adventure that you find quite annoying?
20. Which Of My Adventure Experiences Made You Laugh So Hard That You Cried?
This is another question you can ask your best friend to know the joyful experiences that you have had with them.
The remembrance of such moments will further create an atmosphere of amusement that will create a stronger bond between you and your friend.
Synonymous question:
- What’s the funniest thing I’ve ever done?
In Closing
These 20 questions are put together specifically to make you laugh and enjoy fun conversations with your best friend.
Don’t forget that it is all about fun, so the criticism that you may get in response to your question is also part of the fun, so enjoy!
