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Best Questions to Start a Conversation

Max. D Gray
By Max. D Gray. March 19, 2020
Best Questions to Start a Conversation

Finding good conversation starters to break the ice is not always easy. When it is someone you don't know, it is particularly tricky. However, even long-term friendships sometimes need a little refreshing. Perhaps you have felt like you are not able to communicate as well as before. They may even be a little down and you want to help them by starting a conversation. It can also happen that we are having trouble communicating in our relationship, so we want to ask our partner questions to help start a conversation.

Whether you want to start a conversation with a date, practice for an ESL test, speak more to your partner or you want conversation starters for friends, it's great that you are looking for a little help. oneHOWTO brings you over 100 of the best questions to start a conversation so you can get to know people better.

You may also be interested in: Absurd Questions to Ask Friends


  1. Conversation starter questions for someone you like
  2. Conversation starter questions for a partner
  3. Conversation starter questions for a friend

Conversation starter questions for someone you like

Finding things to say to someone you like is not always easy. Even if you are normally quite confident, it is common we might get tongue-tied around someone we have feelings for. These questions should be kept light and fun at the start to break the ice and stay calm. However, if you really want to get to know someone, then you might want to ask some deeper questions.

Here we provide conversation starters for a date with fun and interesting topics to get to know someone:

  1. What would a perfect day be like for you?
  2. What is the worst date you have ever had?
  3. When you were little, what did you want to be when you grew up?
  4. What is the craziest thing you've done to get someone's attention?
  5. How would you describe yourself in three words?
  6. If you could have a super power, what would it be?
  7. Is there a story you like to tell?
  8. What is something you can't stand about society?
  9. How many times have you fallen in love?
  10. Do you believe in love at first sight?
  11. If you could change just one thing about yourself, what would it be?
  12. How do you like to meet people?
  13. What music makes you think of the happiest moments of your life?
  14. What would you say is your greatest weakness?
  15. At what point in your life have you been most ashamed?
  16. What do you value most about your friends?
  17. How do you see yourself in 5 years?
  18. Is it easy for you to trust others?
  19. What type of music or song best defines your personality?
  20. Do you consider yourself a person with initiative? Or do you prefer others to take it?
  21. Do you think love can last forever?

If you are looking for conversation starters with a girl or boy which are a little more adult orientated, then we have some options for you below. Bear in mind, there is a fine line between flirty and creepy. Work up to the spicier ones or you may scare the other person off.

  1. What do you find most attractive in a person?
  2. When do you feel sexiest?
  3. What is the strangest place you have done it?
  4. Is there someone you regret sleeping with?
  5. What do you think about sexting?
  6. What score would you give yourself in bed?
  7. Would you dare to have a threesome?
  8. Is there anywhere you would like to do it, but haven't?
  9. What part of my body do you like the most?
  10. Do you have any particular fantasies?
  11. Do you have a fetish?
  12. Would you like to try tantric sex?
  13. Did you ever have fantasies with me before you met me?
  14. What is the most memorable erotic dream you've ever had?

One of the most fun ways to get to know someone is by playing ‘would you rather?’. That's why we have the best would you rather questions and topics to ask anybody.

Conversation starter questions for a partner

Do you feel like things in your relationship are getting a little stale? Maybe you have realized when you started going out with your girlfriend or boyfriend, you didn't know that much about them. Equally, you might just want to get to know that special someone better or discuss new topics. The best questions to ask your boyfriend or girlfriend include:

  1. Do you think you look like your parents?
  2. What is a very good day for you?
  3. Do you ever get jealous?
  4. If you could be anyone else in the world, who would you be?
  5. Would you like to see into the future?
  6. Can you imagine marriage?
  7. If you had children, what would you like to call them?
  8. If you could only listen to one singer or group for the rest of your life, what would it be?
  9. What movie always excites you?
  10. What song makes you think of me?
  11. When do I seem most sensual to you?
  12. What do you do to cheer up someone who is sad?
  13. What is the worst mistake you think you have made in life?
  14. If there were no laws for a day, what would you do?
  15. Who are the five most important people in your life?
  16. What pet would you like to have if you could choose from any animal?
  17. What three adjectives do you think define me the best?
  18. Do you think you know me?
  19. If you could be famous for one day, what type of famous would you be?
  20. If you could have dinner with a person, living or dead, who would it be?
  21. Could you forgive infidelity?
  22. Why do you think there are so many divorces?
  23. When did you know you were in love with me?
  24. What do you dislike most about me?
  25. Which celebrity do you find most attractive?
  26. If you could resurrect a person, who would it be?
  27. What do you think is a truly romantic gesture?
  28. What is something that always makes you sad?
  29. What book has meant the most in your life?
  30. Would you like to be another gender for a day?
  31. What is something that always makes you laugh? A movie, story, situation, etc.
  32. If you knew when you are going to die, would you change your way of living?
  33. What kind of people pity you the most?

These are questions to pose to a woman or manwith whom you are close. Even the game ‘never have I ever’ can be a fun way to talk about new things. However, be advised some of them may bring up topics which you might not want to explore during a rocky patch. Being honest is necessary for a relationship, but you may also need to be tactful at times.

If your partner is away and you miss them, you may have to rely on messaging services to have a conversation. These romantic WhatsApp messages for your partner might be helpful.

Best Questions to Start a Conversation - Conversation starter questions for a partner

Conversation starter questions for a friend

While our friends are the ones we should usually be able to chat to the easiest, there are times when this may be difficult. Maybe there has been a change in the relationship, they have gone through something which has made it difficult to talk or maybe you were never great at chatting in the first place. These fun, entertaining, interesting and intriguing questions can help you chat better with a friend:

  1. If you could only watch 3 movies for the rest of your life, what would they be?
  2. What song makes you dance non-stop?
  3. What matters most in a good friend?
  4. Do you think we like the same type of people?
  5. Do you believe in ghosts?
  6. Do you believe in parallel worlds?
  7. What would be your dream job?
  8. If you could be famous for a day, what would you do?
  9. What celebrity would you like to spend a crazy night with?
  10. If you were president, what is the first thing you would do?
  11. What piece of clothing would you like to war, but fear you can't pull off?
  12. What is something you find irresistible of the opposite sex?
  13. And of your same sex?
  14. Have you ever thought about changing sexual preference?
  15. What would you eat for your last meal?
  16. What do you want most in life?
  17. Where you would most like to live?
  18. If you had to live with someone for the rest of your life, who would it be?
  19. What kind of tattoo would you get?
  20. Have you ever fallen in love with a friend?
  21. What do you miss most about your childhood?
  22. Would you rather be the most attractive, but poor person in history or the ugliest and richest?
  23. What is your most precious asset?
  24. What do you do to relieve stress?
  25. Are you afraid of getting older?
  26. What scares you the most?
  27. Is there someone you hate?
  28. Which of our friends annoys you the most?
  29. If you could be part of any band at any time in history, what and when would it be?
  30. What is a guilty pleasure you can admit?
  31. What's the grossest thing you've ever done when you thought no one was watching?
  32. What is the strangest thing that has happened to you in life?
  33. Do you have a useless talent?
  34. What food would you never try?
  35. What is the biggest lie you have ever told?

Whether your friend is a boy or girl, man, woman or however they identify, getting to know them better is not only fun, it will improve your friendship. You may also want to get to know people over social media as many of us have friends all over the world. In this case, you might want to check out these Instagram poll questions to get you started. Instagram quizzes are also a great way to get to know people.

If you want to read similar articles to Best Questions to Start a Conversation, we recommend you visit our Toys & Games category.

  • These conversation starters are for fun, but not everyone will enjoy being asked the same ones.
  • Use common sense and try to elicit what the other person is and isn't comfortable talking about.
  • You can be honest and tell them you are using these questions as a fun ice breaker.

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Best Questions to Start a Conversation