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Weird Conversation Starters

Starting conversations is a great way to get to know people. When you want to be the silly one in the room, asking weird conversation starters might be the right choice for you. Questions like, “If you could eliminate any fictional character from the world, who would it be and why?”

Try out some of these very weird conversation starters!

P.S. I really like this YouTube video for conversation starters.

Weird conversation starters
Weird conversation starters

My own experience with conversation starters…

Well, here’s the harsh truth… I wasn’t the coolest kid growing up. I had a difficult time connecting with others. I don’t know if it was because I was shy. Or I just didn’t feel like everyone else… Very unclear.

But here’s what did help me… breaking out of my shell a bit. The more I did it, the more I learned about myself and the others around me. Questions like these can help! Trust me!

Here are my best tips before you go asking questions:

  • Tailor your questions – Sounds simple… Tailor the question you are going to ask based on the person you are asking it to. Doesn’t matter if it’s a friend, crush, guy, girl, Bumble/Tinder match. Look at who they are.
  • Be yourself – Pick a question that matches you. Don’t just choose any question to try and please the other person. Be yourself… This is what works long-term! Why? Well, when they like you, it’ll be for YOU!

Weird Conversation Starters For A Girl:

Starting a conversation with a guy is not as easy as it seems, regardless of whether you know each other personally or just found their profile on a social network.

Sample Questions:

1. Would you like to switch bodies with someone?

2. Did you give a bouquet of 101 roses?

3. Have you ever argued about money?

4. Did you find money on the street?

5. Stealing money from your parents?

6. Dreamed of a gift, but it was never given?

7. Spying on the girls in the locker room?

8. Have you ever put chewing gum under the table?

9. What hairstyle have you always coveted but dared to try?

10. What is your attitude toward loneliness?

11. Have you done something kind recently?

12. Are you afraid to be yourself around other people?

13. If your worst fears came true, would it matter five years later?

14. Do you take other people’s advice?

15. Do you consider yourself a pleasant person?

16. Do you enrich the lives of others?

17. Do you have a purpose in life?

18. Would you sacrifice your life to save the life of another person?

19. How much are you prepared to give to help the poor?

20. What would you do on the same day if you could repeat it endlessly?

21. What is the primary trait you seek in others?

22. Do you believe you are significant and deserving of love and adoration?

23. How would the world have changed if you were never born?

24. What would you be if you could change who you are?

25. What does success mean to you at age 28?

26. Which life lessons do you wish you had known ten years ago?

27. Would you like to see your life if it were a movie?

28. What one piece of advice would you give to the youthful version of yourself?

29. What would the name of your life’s film be if it were one?

30. What qualities do you value most in a woman?

31. What bad habits would you like to give up?

32. How would you title your autobiography?

33. Imagine that you are very rich and you no longer need to work. What would you do?

34. Which would you choose: living on the moon or in the ocean?

35. If you lost all your money, would you rather lose all your photos?

Would you prefer to have the ability to fly or turn invisible?

37. Do you like to reside in a hot or cold climate?

38. Do you like to arrive a little late or a little early consistently?

39. Which would you rather give up: your computer or smartphone?

40. Would you rather live without social media or heat and air conditioning?

41. Which would you like to possess in a group: intelligence or humor?

42. Which would you choose: to fly at 10 km/h or to run at 100 km/h?

43. Would you rather be the world’s top cook or a superhero?

44. Would you rather be an astronaut or an Olympic gold medalist?

45. How many languages ​​do you know?

46. What is the strangest food you have ever eaten?

47. If you could teleport right now, where would you teleport to and why?

48. If you could eliminate one thing from your daily routine, what would it be and why?

49. What’s the most unusual thing you’ve ever done?

50. If you were on a reality show, which show would you choose and why?

Related: Good conversation starters for texting

Weird conversation starters
Weird conversation starters

Weird Conversation Starters For a Guy:

Some weird conversation questions to use on guys that you want to spark a conversation with.

Sample Questions:

1. Would you like to be a different gender?

2. Do you believe in corruption or the evil eye?

3. Do you feel the mood of other people?

4. Do you want to be on a desert island alone for at least a day?

5. Could you live a month without a phone and the Internet?

6. Would you be able to drink blood in a hopeless situation?

7. Do you snore at night?

8. Would you like to be friends with a celebrity?

9. Do you live in a house on earth?

10. Do you believe in aliens?

11. Do you open something with your teeth?

12. Do you often go to the toilet before an important event?

13. Do you bite your nails?

14. Would you like to live by the ocean or the sea?

15. Would you like to do nothing all day long: just eat and sleep?

16. Do vampires exist?

17. Do you believe in miracles and Santa Claus?

18. Which class would you pick if you had to attend one for the rest of your life?

19. Have you ever engaged in combat on school property?

20. Have you ever slept off in a class?

21. Do you have any prior suspension or detention history?

22. What feature are you getting complimented on?

23. Which boy, out of everyone in the room, would you accept to meet?

24. Which guy would you never date out of everyone in the room?

25. How long can you be silent?

26. Is there some secret that no one knows about?

27. What do you not like about food?

28. What have you never tried?

29. What was the dumbest thing you did?

30. Which trait or feature about yourself would you wish to improve?

31. What was the weirdest incident that has happened to you in public?

32. Describe the worst mall incident you’ve ever experienced.

33. What has been your cruelest remark to a person?

34. Have you ever considered defrauding your boyfriend?

35. What is a rumor or piece of gossip that you spread about someone but afterward discovered untrue?

36. Do you prefer jocks, intellectuals, nerds, or bad guys?

37. Have you ever flirted with your best friend’s brother?

38. If you were stuck on an island, who would you like to be stuck with?

39. If you could marry a celebrity, who would it be?

40. Do you ever just look in the mirror and admire yourself?

41. Have you ever been dumped on a date?

42. What can quickly lift your spirits?

43. What will make you laugh to tears?

44. Where would you like to spend your vacation?

45. What stupid things did you do that you won’t repeat now?

46. Funny, funny, ridiculous situations that you got into?

47. How do you have fun with your friends?

48. What is the strongest character trait?

49. Are there bad habits that you struggle with?

50. What is the funniest thing at your school that one of the teachers has done?

Weird conversation starters
Weird conversation starters

Funny and Weird Conversation Starters:

Funny conversation starters that are also quite weird!

Sample Questions:

1. What’s the grossest prank you’ve ever played on someone?

2. What do you think your boyfriend thinks about marriage and children?

3. Have you ever urinated in a public pool?

4. If you suddenly became invisible, what will you do first?

5. Who has the most sensual sense of fashion in this room?

6. If you could only have one companion on a desert island, who would you choose?

7. What is your darkest, most abiding phobia?

8. Have you ever been the victim of someone else’s betrayal?

9. What are the things that you are aware of in yourself?

10. Describe the one thing about you that most people believe to be true yet isn’t

11. Have you ever absolved someone else of responsibility for your actions?

12. What have you done that people said you would never do?

13. Have you ever run into a police officer?

14. What is an idiotic item you have a strong attachment to?

15. What did your parents catch you doing that was the most embarrassing thing?

16. Have you loved someone who didn’t love you back?

17. What is it that you have never told anyone about?

18. Do you lick your plate after finishing your meal?

19. What part of your body do you hate, and what do you love?

20. Have you ever had lice?

21. Have you ever been caught red-handed doing something you shouldn’t have done?

22. Have you ever eaten something straight from the floor?

23. Do you have a special blanket?

24. What would you eat if you could eat one thing without gaining weight?

25. Do you sing or dance in the shower?

26. Have you ever peed while laughing?

27. Have you ever talked to yourself?

28. Do you sleep with a soft toy?

29. Do you ever drool in your sleep?

30. Would you sell your dog for a million dollars?

31. How many eggs can you eat on an empty stomach?

32. Why do you go to bed when you want to sleep?

33. Would you rather live in a fantasy or superhero world?

34. How would you tease your friends if you were invisible? 

35. What would you do if you woke up as a monkey?

36. Can you wink with both eyes?

37. If animals made documentaries about humans, what strange things would they show?

38. How will you scratch your back if your hands are tied?

39. If videos of human failures bring success and millions of views, then what is failure?

40. Why do girls in pants look okay, but guys in skirts don’t?

41. Why is chocolate not a vegetable if it is made from cocoa beans?

42. If I suddenly become an animal, will you make me your pet?

43. How did women shave their legs in ancient times?

44. Is it fair that a carrot is more orange than an orange?

45. What are you grateful for?

46. What will you regret not doing in your life?

47. What is the wisest thought you have ever heard?

48. What have you learned from your bitter personal experience?

49. How often do your most substantial anxieties and fears come true?

50. Have you recently done something that you are proud of?

Weird conversation starters
Weird conversation starters

Weird Conversation Starters for a Date:

Weird conversation starters to use on dates!

Sample Questions:

1. Do you want a baby?

2. How long can you stay underwater without breathing?

3. Can you drive a car?

4. What kind of dreams do you have?

5. Would you like to skydive?

6. Do you like solving math problems?

7. Do you like reading?

8. Do you like to walk barefoot?

9. Are your parents strict?

10. Do you like ice cream?

11. Do you bite your nails?

12. How often do you take a bath/shower?

13. How often do you wash your hair?

14. Do you like to shave?

15. Do you like to clean your apartment/room?

16. How often do you clean your apartment/room?

17. What is the relationship with parents?

18. Do you know the pedigree of the family?

19. What is your blood type?

20. Do you love brushing your teeth?

21. Do you often quarrel with loved ones?

22. What is the most reckless act you’ve done?

23. Do you lie often?

24. What was the last time you were embarrassed?

25. Is there a person you hold a grudge against?

26. Is there something you want to do but are afraid to do?

27. Have you ever been in a hospital?

28. Have you ever ridden a motorcycle?

29. Have you ever ridden a catamaran?

30. Do you want to visit space?

31. Would you like to fly into space?

32. Would you eat a cockroach for a million dollars?

33. Do you believe in higher powers?

34. Do you want to sing karaoke?

35. Can you reach your nose with your tongue?

36. Can you roll your tongue into a tube?

37. Can you hold your breath for 1 minute?

38. Can you not brush your teeth all day if you don’t go out?

39. Can you endure pain because of the fear of doctors?

40. Will you bungee jump on an argument?

41. Would you like to shave your head?

42. Would you like to spend a day on a yacht in the open ocean?

43. Do you hate mosquitoes?

44. Would you like to travel the world for a lifetime?

45. Would you like to have cubes on the press?

46. Have you ever seen a dolphin in your life?

47. Would you like to swim with a dolphin?

48. Would you like to read people’s minds?

49. Are you afraid of horror?

50. Are you afraid to be alone at night in scary places?

Funny Conversation Starters You Can Ask Anyone:

Funny conversation starters that are quite weird, where you can use them on just about anyone!

1. If you had friends all over the world, how would you communicate with them?

2. If you had to come up with a new holiday, what would it be?

3. Do you come up with any inventions?

4. Do you think learning a foreign language is fun?

5. What animal would make a first-class driver?

6. What makes your friends so amazing?

7. What do you like most about wildlife?

8. If you were the hero of a computer game, who would it be?

9. How do animals communicate with each other, in your opinion?

10. Imagine being able to spend all day outdoors: what would you do?

11. If you could ask any question to a wild animal, what would you ask it?

12. What would it look like if you could build yourself a house or a cave in the forest?

13. What will you think about before going to bed tonight?

14. What will people say about you at your funeral?

15. Do you think sleep should be listed as a mandatory hobby when applying for a job?

16. Imagine yourself as a chef and tell me about your restaurant. What food would be on his menu?

17. What would your tree house look like?

18. What do you like to do for other people?

19. Did anything make you laugh or laugh today?

20. What would it be about if you were to write a book?

21. What would it be if you could draw anything that comes to mind?

22. what do you think they would talk about if animals could talk?

23. What would it be f you could grow something in your garden?

24. Imagine that you are on the beach right now. What will you do first?

25. What is your Superhero’s name and what powers does he have?

26. What would you sell there if you were to open a store?

27. Which character makes you laugh the most?

28. Have you ever wanted to change the colors of familiar things?

29. What do you think about when you wake up?

30. Do the people you love the most know how you love them?

31. Given your current daily life, what do you expect to achieve in five years?

32. What is your funniest goal in life?

33. Let’s be honest, how often do you work while lying in bed?

34. How many cups of coffee/tea do you drink per day?

35. What do you think is the best professional literature?

36. If you want to survive the zombie apocalypse, assemble a team of three people who would you pick?

37. What type of transport do you like the most?

38. Consider running your talk show. To whom would you extend the initial invitation?

39. What would it look like if you were a fashion designer?

40. What do you think is one of the most extraordinary scientific discoveries?

41. If you had to remove all but three apps from your smartphone, what would you keep and why?

42. What is your favorite magical or mythological animal?

43. Who is your favorite character from a fairy tale?

44. Imagine that you are about to sail around the world. What would you name your ship and why?

45. If you were an Olympic athlete, what sport would it be and why?

46. Who do you consider the best in the business world and why?

47. What musical group or artist would you like to invite to your holiday?

48. What do you like to eat for breakfast?

49. What is your favorite time of day and why?

50. If you had a time machine, would you travel to the past or the future?


Fact checked:
Board reviewed by Marianne Tomlinson, LCSW (Couples and Family Therapy). Content is rigorously reviewed by a team of qualified and experienced fact checkers. Learn more.

About the author

Ryan Sanderson (LCSW) Ryan is a game and relationship enthusiast who enjoys all things quizzes, games, fun, love, relationships, and family. He's a licensed social worker and helps families, couples, and children in need. He's spoken about love and relationships on Salon.com, Forbes, and Mirror, to name a few.

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