21 Questions To Ask A Guy or Girl Over Text To Keep A Conversation Going Interestingly

Here are thoughtful and funny 21 questions to ask a guy or girl over text to keep a conversation from dying.

Imagine the scenario,

He/she texted “hello”, and you replied “hi”-.

Then there goes the awkward silence…

After some minutes of silence, you decide to break the silence by asking him/her if he had a great day?

unfortunately, his reply brings the conversation to an end. This is because you both are stuck for words. You wish to continue the conversation but, you just can’t think of an interesting question to get him/her talking.

Does the above scenario describe your situation? Yeah, I know you might feel weird about not being able to have an interesting conversation with a partner or friend. I mean, you have lots of questions to ask your partner or friend but once the opportunity presents itself, you just don’t know how to go about it.

Well, it is not unusual. It happens to virtually everyone at one point in their lives, especially if you are the type that hates intruding in people’s personal lives or you are just a person of few words. That notwithstanding, let’s focus on the sunny side of life and that entails you having an interesting, fun-filled, heartwarming conversation regardless of your personality traits or the level of intimacy you have with your partner/friend.

For this reason, I am glad to tell you that I have compiled questions not just any questions but, Good 21 questions to ask a guy or a girl over text to keep a conversation going.

Interesting 21 Questions To Ask A Guy

When it comes to relationships, it seems the male folk is at the forefront of all decisions. Like, they do all the wooing, they ask a lady out and they also propose to their love interest.

However, relationship is not a one_sided thing, right? For every form of relationship, the two parties involved must be willing to show commitment through their actions and inactions.

Yeah, I know those physical attributes already meet your spec. But, beyond those broad shoulders, well-trimmed beard, beautiful dentition, and a perfect accent, lies some weird and unpredictable qualities.

So, rather than leave him to ask all the questions, you should also uncover the weird, good, bad, and fun side of him with these interesting 21 questions to ask a guy.

1. Have you gone on a date with someone before? If yes, what was the experience you had?

2. What is the greatest weakness that you wish to overcome?

3. What motivates you during your downtimes?

4. Is there someone you admire secretly? If yes, what do you admire about him/her?

5. What is the lamest excuse you’ve ever given?

6. Which country will you love to visit before growing old?

7. Have you ever cheated on someone before?

8. If you are given an open cheque to make three wishes that will be fulfilled, what will they be?

9. Would you rather be with the love of your life or with a celebrity you admire?

10. Have you ever had a first kiss?

11. What is the one thing you won’t be caught dead doing?

12. What do you see friends as? A liability or an asset?

13. What is the biggest lie you’ve ever told yourself?

14. Which of your hobbies will you keep doing even if you are paid to stop?

15. How will you react to someone telling you that she has fallen in love with you?

16. What is your opinion about Sex?

17. What do regret doing as an adult?

18. Can you share your phone password with your partner?

19. What is fulfillment to you?

20. How do you handle the pressures of life?

21. If your love life was music, what song will you sing?

Related Post: Question-Game for Couples

Romantic 21 Questions To Ask Your Crush

Who doesn’t have a Crush? Crushing on someone is so common with everyone. Some had a crush on their boss, colleague, classmates, or even mentors.

If you think crushing on someone is not for you, then I’m sorry to burst your bubbles you will crush on someone someday. This is because every day of our lives, we get to meet or see people who we think are smarter, beautiful, intelligent, or generally more endowed.

The beautiful ones are not yet born and there will always be that one person that gives you the butterflies.

Yeah, many can resonate with that overwhelming feeling of infatuation, a palpitating heart, constant daydreaming, and blushing from cheek to cheek whenever they set their eyes on their crush. But then again, there are myriads of questions that accompany crushing on someone.

Some of these questions include; does he/she feel the same way towards me? how do I approach him/her to confess my feelings? will he/she be annoyed if he/she gets to know about my little secret?

The answers to these questions are not far-fetched and you don’t have to hide your feelings for your crush because of doubts and fear.

I mean, why crush on someone when you can’t let him/her know about your feelings. Being vocal about your feelings for him/her will either open a door of a romantic relationship with him/her or a door of friendship.

Either way, it’s gonna be a win-win for you, and that’s why I have not just compiled Good 21 questions to ask a guy or girl over text to keep a conversation going, but I have also put together these Romantic 21 questions to ask your crush.

1. If you could say just three words to me, what would they be?

2. Have you ever thought about someone you love the whole day?

3. Have you ever loved wrongly?

4. Do you believe in love at first sight?

5. What’s the weirdest gift you’ve ever received from someone you love?

6. Would you rather fall in love with a stranger or fall in love with your best friend?

7. How do you express how you feel about someone you love?

8. would you rather have an unrequited love or unattainable goals?

9. Have you ever had a failed relationship?

10. What is a “perfect day” for you?

11. What drives you to become better each day?

12. If fear and doubt weren’t an issue, what is that one bold step you would love to take?

13. Would you rather have a happy ever after kind of love story or have no love story at all?

14. How do you deal with sexual advances from the opposite sex?

15. Would you rather be called a faithful lover or a faithful friend?

16. What is your love language?

17. If allowed to spend a whole day with someone you admire, who will that be?

18. Do you ever wish to be someone else?

19. Would you rather receive gifts from loved ones on your special day or have them spend the entire day with you?

20. What is the one word that best captures your love interest?

21. What do you find most difficult to do, Earning the respect of the one you love or asking for his/ her forgiveness?

Related Post: Topics To With Your Boo When Bored

Top Good 21 Questions To Ask A Girl

Oliver was asked by his father,” Son what do you have to say about girls?

He replied thus, girls mean a whole of things to different people.

They are called mothers by some people.

They are girlfriends to some.

To others, they are sisters that will always have their back.

Finally!, he exclaimed loudly, they are the most complicated creature on earth. They long to be understood but don’t make understanding them easy for people like us.

Are you in the same situation as Oliver? You are in a relationship and You’ve employed different strategies to get to know her better. But it seems you just can’t break through her Coyness. Each passing day she leaves you with lots of questions that you can’t seem to find answers to.

Or you just met her, but you desire to be more than a friend to her. You want to know the nitty-gritty of her personality, then you are on the right track with these good top 21 questions to ask a girl.

1. Would you rather have a drink on a first date or a cup of ice cream?

2. Will you be able to forgive a cheating partner?

3. How much are you willing to sacrifice for the sake of love?

4. Do you have a milestone you will love to attain in life?

5. Have you ever told a lie about your best friend?

6. Can you go out a whole year without having your make-up on?

7. Would you rather have to deal with a stalker or a lying friend?

9. Which of your favorite song would you love to be played on your special day?

10. Do you love to be called by your nickname or your real name?

11. What is your most embarrassing moment?

12. Have you ever lied about your age?

13. How do you want to be always seen by people?

14. Do you think loving someone is a waste of time?

15. What is your definition of a real friend?

16. How long do you think is ideal to date a guy?

17. What is your favorite quote?

18. Would you rather be every man’s dreams or every man’s nightmare?

19. What is your opinion on body enhancement?

20. What is the craziest thing you’ve done for the sake of love?

21. Would you rather be with a Romantic partner or an honest partner?

Good Conversation Topics For Texting And Chatting

Whether is a newfound friend, an old friend, a partner, colleague, or a crush. The purpose of every good conversation is to show genuine interest in people, spark connections and build healthy relationships.

Technological advancement has made it possible to have a healthy conversation with people even without seeing them. Online platforms like Facebook, whatsApp, Twitter, etc have made it possible to have a good conversation with strangers and friends even from the comfort of your room or office.

Yeah, you don’t have to get too nervous or be self-conscious, because the conversation is text-based and therefore gives you time to think about what next to reply or ask.

However, if you still struggle with coming up with questions to ask, here are good conversation topics for texting.

1. Which of your traits will you not like your children to have?

2. How do you appreciate the special people in your life?

3. What unforgettable life lessons have life taught you?

4. Do you have a favorite book you’ve read? What made it your favorite?

5. How do you celebrate your big and small wins?

6. Have you ever regretted showing any kind gesture?

7. What phobia did you have as a child?

8. What is the best investment decision you’ve ever made?

9. Do you have a childhood friendship that lasted till adulthood?

10. Have you ever broken a promise you made to someone?

11. If I’m given access to your phone, what are the first three apps that I will see?

12. Would you rather have a personal diary or a confidant?

13. Which social media platform do you enjoy the most?

14. What is the worst treatment you’ve ever gotten from a stranger?

15. Have you ever followed your instincts and ended up regretting it?

16. What do you do when you lack the inspiration to finish a project?

17. Have you ever made a birthday wish that came true?

18. Is there any part of your body you would love to change?

19. What is your preference when it comes to books?

20. What can you teach anytime even without being prepared?

21. Will you be willing to support a cause that is contrary to your beliefs?

Questions To Ask Over Text To Keep A Conversation Going

Starting a conversation is not the big needle mover, but rather maintaining the flow and engagement.

And, this doesn’t have to be difficult. You just have to show genuine interest in the conversation, and be more dynamic by asking open-ended questions.

Let’s say instead of asking the recipient of your text ” how was your day? you can ask what made your day memorable?. In that way, one answer leads to another and then the conversation gets rolling.

That said, in addition to Good 21 questions to ask a girl or guy over text to keep a conversation going, I have put together more questions to ask over text to keep a conversation going.

1. What fuels your passion for your job/career?

2. Each day comes with its challenges, how do handle everyday challenges?

3. Which of your traits sets you apart?

4. Do you see procrastination as life-threatening? if yes how do you deal with it?

5. What footprints will you like to leave on the sands of time?

6. What is your perception of Mondays?

7. If you are allowed to correct just one past mistake, what mistake will that be?

8. What is your opinion on love and relationships?

9. What are your long-term goals?

10. Falling in love with someone is a beautiful experience, what is the funniest thing you’ve ever done because of love?

11. What is success and happiness to you?

12. When do you doubt yourself the most?

13. What is the best relationship decision you’ve ever made?

14. How do you deal with the feeling of underachievement?

15. What are those bad habits you have struggled to overcome?

16. What are the things you look out for in a man/woman?

17. What is your most adventurous journey?

18. If you are to choose just three important things in life, what will they be?

19. When do you think is the perfect time to get married?

20. Are there times when you feel depressed? how do you deal with depression?

21. What has been the biggest risk you’ve taken In life?

Things To Text When Conversation Dies

Are there some chats that you would gladly avoid?

You know, those type that is usually characterized by abbreviated text messages like ” BRB, “LOL “TTYL, “IDK” etc.

The truth is when a conversation dies is either the people involved who feel too lazy to text each other and most times resort to the use of short text messages, which is not bad by the way. But when used excessively will make such conversation empty and short-lived.

Another is when one person does all the asking. Every great conversation should have a natural flow. It should not be one-sided. That is, the parties involved should participate actively. But, what happens when one person does all the asking? and the majority of the questions asked are closed questions which usually require yes or no answers.

Do you find such conversation engaging or boring? Your guess is as good as mine.

Therefore, if you’ve ever experienced a conversation that was brought to an abrupt end because you found it boring or you ran out of ideas on what to discuss, here are things to text when a conversation dies.

In addition, you don’t have to think deeply to come up with interesting questions, a fellow up question from the previous one asked might just do the magic.

1. What plans have you put in place to achieve your weekly goals?

This question might be a sequel to questions like, what are your plans for the week? Or what have you been up to lately? This might help to revive a dead conversation. However, you can decide to go a step further by asking the other person if your help will be needed.

2. What is your prediction about this weekend’s football match?

Talking about trends, or hobbies can also make a dead conversation come alive. More so, it doesn’t have to be about football trends only, it can be fashion, movies, literature, politics, etc. That said, your questions must also align with the other person’s interest, to enhance a more engaging conversation.

3. What is your best method of communication, calls, or chat?

Most people are not great at chatting, they would rather spend hours on a call with someone than chat. That explains why every attempt made to start a text conversation with them is futile. For some others, text conversation is just the best means of communication.

Nevertheless, by asking the above question, you will get to know the reasons why the conversation was stalled and therefore find a better approach to prevent its recurrence

4. I love your current d.p, what’s your latest beauty hack?

Compliments are just one of the ways to set the right atmosphere for a great conversation. I mean, humans love compliments, we love to be admired and appreciated. Just one compliment can ease every tension and cause the heart to pour out its content without holding back.

5. Which of the emojis best describes your current mood?

Yeah, if he/she can tell her current mood through an emoji, it can lead to more questions like why he/she is in such a mood. If it’s something he/she will love to talk about, then give a listening ear.

What To Say To Keep A Conversation Going

“A single conversation across the table with a wise man is better than ten years mere study of books”..…….Henry Wadsworth Longfellow.

Despite having these Good 21 questions to ask a guy or girl to keep a conversation going at your fingertips, you should also know when, how and what to say to keep a conversation going.

Your usage of words, that’s the skill of knowing when to say something, how to say it, and what to say is wisdom.

This is because, every conversation should leave one feeling happier, better, and more relaxed. Conversations shouldn’t make us feel miserable, angry, or depressed.

Conversations should be soul-lifting and therefore words should be chosen wisely. On that note, here are what to say to keep a conversation going.

1. You sing so well( can be any other strength the other person has), what are the secrets to great singing?

2. Just came across an acronym today and that is YOLO( You only live once), do you think one should live once?

3. Have you read the news headlines today?, What is your opinion about the recent happening?

4. What are the things you would love to achieve before 30?

5. Will be going on a date this weekend, what color of dress/Shirt best suits a dinner date?

6. What are your thoughts about the present economic policy?

7. Would you prefer an evening workout or a visit to the cinema tomorrow?

8. How do you snap out of an anxious feeling?

9. If you weren’t a man/woman, what would you have done differently?

10. What is the best book you’ve read this year, can you share some thoughts?

Final Thoughts

You do not become a good conversationalist by asking questions like Good 21 questions to ask a girl or guy over text to keep a conversation going.

Howbeit, of great importance, is your ability to listen, respect people’s beliefs and opinions and finally show appreciation for each person’s uniqueness.