20 Deep Questions to Ask a guy Over Text – Be Texting Expert !

deep questions to ask a guy over text

Is it hard for you to text? Don’t know what to ask him? Don’t worry; here are questions to ask a guy over text. He is going to love replying to all these great questions. Sit back and read all those questions.

deep questions to ask a guy over text
deep questions to ask a guy over text


Question 1: What’s your worst restaurant experience?

We all experience different things at restaurants. Your guy probably has a couple of stories to tell you. And who doesn’t like experience gone the wrong story? He will love to tell you about those specific restaurants. He might warn you about those restaurants.

Question 2: Does someone in your life lost his/her respect from you?

It is the best question from our deep questions to ask a guy list. What makes him hate someone? What are the things that matter a lot to him? The answer will open a new personality of him in front of you. He will never tell you this if you ask him directly. It’s an indirect way to know his peak factor of hate, which makes him hate people.

Question 3: Is our government treating people the right way they should?

Yes, it’s a deep question. And it can lead to a long conversation if your guy is more into politics and country. Even if he is not that interested in politics, he will still reply with lengthy arguments. It is no doubt a deep conversation topic, or you can say a deep question to ask a guy.

Question 4: If you have the option to choose your job for a lifetime? What would it be?

More like a dream job. The job that makes him happy. He will tell you about his inner passion. What he wanted to be. Or you can say you will also know his satisfaction level for his current job.

Question 5: What is your most outstanding achievement so far?

Even if he has done something minimal, you must appreciate him for his efforts. Make him feel proud of what he has done. It should be something positive that doesn’t make him feel proud of negative things.

Question 6: Have you done anything to make our world a better place to live?

It’s a different question from the previous question. The last question was about himself. In this question, you are looking for his inner soul about others, what he feels about other people in the world, how he is looking at other people.

Question 7: Who inspired you most in life?

Anyone can inspire us. The inspiring person can be a bodybuilder, runner, any film actor, or a social guy who means a lot to us. So asking for his inspiration will tell you a lot about himself as well.

Question 8: How you deal with haters?

It is an open question on handling haters. He all have people who hate us for no reason. How we deal with them is an excellent way to know about a person.

Question 9: How you define yourself in a sentence?

This question is more about knowing him personally. The question is also fun. He will love to create a sentence for himself.

Question 10: What is a dream trip for you?

This question is about knowing his dream trip, what is in his mind about a dream trip. You will also enjoy old memories, so use this question when he is in a good mood.

Question 11: Who is your best friend? And why?

It is an excellent question to ask a guy. Guys love to talk about their best friend if they love them. If your guy is not openly talking about his best friend, that means he is not that close to his friends, and it’s a good thing for you. You will get more time even if he has 2, 3 best friends, that completely fine. Guys love to hang out with boys.

Question 12: Suppose if you have kids, do you have any memorable life stories to tell them?

If you are interested in listening to his life stories, ask him this question. He might tell you some of the most exciting stories from his life. The question is a supposition, but make you guys laugh.

Question 13: Are you proud of something?

To know him better in the sense of his achievements in life, this is a perfect question. Don’t hesitate to ask. Just ask this question, and he will tell you a lot about his achievements in life.

Question 14: What was the worst gift you have ever received?

Yes, Guys love to gift stupid stuff to best friends on birthdays or special events. Asking this question will make you both laugh. If he hasn’t received something stupid from friends, that means he is not that much attached to his friends, or all his friends are mature.

Question 15: Who is your closest family member?

If you want to know about his family and his relationship with family members, it’s a lovely question to ask a guy.  Just ask this question, and he will definitely like your interest in his family.

Question 16: Who is your favorite anchor in TV shows?

Yes, it’s a generic question, but it’s an excellent way to interact and have something to talk about instead of looking at each other with awkward silence.

Question 17: Do you daydream? What you mostly dream of in the day?

All guys do daydreaming about different things. It’s an exciting topic to talk about with guys. Initially, he might not tell you about his daydreams, but if you just help him with your stories, he will open up.

Question 18: What’s your favorite joke?

If you guys want to laugh, ask him this question. Listen! If you already knew about the joke he was trying to convey, react like you just heard it. Try to let him feel that the joke was hilarious and be natural, don’t fake it.

Question 19: Do you believe in myths e.g., mermaids do they exist?

It’s a fascinating deep question to ask a guy. Such questions can be answered with different thoughts. Let him speak about the topic. You can prolong the conversation by adding a few more myths in your talk.

Question 20: Can you tell in advance if someone is going to be successful or failure?

It might look like a straight and straightforward question, but in reality, it’s more about his observation in people how he observes things around him. On what parameters he judges people. What is his definition of success? How different he thinks.


So these were all the questions to ask a guy over text. I hope you enjoyed reading these. Thank you

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