140+ Personal Questions to Ask a Guy [Deep & Personal Questions]

Do you often wonder what questions should one ask guys and especially the shy ones who do one speak at once? Guys also guard their emotions and in such situations, the two of you often tend to lose connection. You want to bond deeply but the other person hesitates to speak. So, what’s the solution?

When you wish to know a guy on a deeper level and in abundance, you need to be good with conversation. We have prepared a wide variety of personal questions that you can ask a guy. They can be very useful not only in terms of knowing each other but also for creating ease of comfort between you two.

These sets of questions will help you break the line of ice and awkwardness between you both and will prove as a conversation starter. Good questions and interesting answers always lead to beautiful conversations.

Asking the right questions will give him a boost and he may feel like sharing his feelings with you. Target his mind and don’t sound overpowering as this may result into him becoming more reserved. Pick what you feel is good and do not push too hard on him.

There are few ‘go-to’ personal questions while some of them are a little tricky. Both are good depending on the situation between you both. Using such questions may reveal few secrets also about them.

Personal Questions to Ask a Guy

Here is the list of personal questions to ask a guy:

  • How do you manage stress in daily life? What all steps do you take to maintain your mental health?
  • Is there anything/anyone who inspires you the most? Who do you look upto in life?
  • What are your opinions on relationship? Have you ever been into one? Has someone broken your trust in love?
  • What according to you is your strength and weakness? Do you do anything to overcome your weaknesses?
  • Which type of movies do you usually watch? Which one are you watching these days?
  • What are your thoughts on online dating? How safe do you think they are? Have you ever tried?
  • What is the craziest thing you have done to gain attention in your childhood or even after getting matured?
  • What do you want to do when you are angry or frustrated with someone/something?
  • Have you ever broken someone’s heart intentionally? If yes, do you have regrets about that?
  • How mischievous were you in school and how often you got punishments from the teacher?
  • Which is the one thing you never want your parents and family to know about you?
  • Are you religious? Do you sit with your grandparents or elders and do prayers and attend religious family functions?
  • Are you into retro music? What is your favourite song?
  • Who are you close to in your family? Were you insecure when you sibling was born?
  • What phase of life you think you are in right now? Is there anything you want to add in life or get away from something?
  • How old were you when you realised that career is important and so is family?
  • What is the most romantic thing you have ever done for a girl? Did it work out?
  • Do you forgive people easily? What do you think when someone apologises to you?
  • What according to you is actual waste of money? Have you ever spent on something expensive and then regretted?
  • What is a simple positive change you want to bring in your life?
  • What is the biggest lie you have ever told to someone?
  • Do you have anger issues? Do you lose your temper easily?
  • What are your biggest dreams and goals in life?
  • When you think about your future, do you see me contributing in your life in any form?

Questions To Ask A Guy To Get To Know Him Deeper

Knowing someone to their core is a lovely feeling. If you wish that the guy should speak to you without any hesitation, you must ask the right questions and at the right time. Allow him some time to answer and encourage him enough to speak the truth. You can also share your experience on the question so he feels that he should also talk and trust you back. 

Here is a list of Questions To Ask A Guy To Get To Know Him Deeper:

  • What makes you happy and what makes you sad the most?
  • Which sport are you into? Have you participated in any of them in your childhood days?
  • What do you think is the main foundation of any relationship and what ;are the steps to maintain the consistency?
  • How has life treated you so far? Has it been gentle or very harsh or a combination of both?
  • Do you like reading books? Who is your favourite author and what genre of books do you prefer reading?
  • What comes to your mind when you hear the word LOVE?
  • Who is your favourite person in the world? How would you describe their physical and internal qualities?
  • Is there anything you are obsessed about? What is the one thing that attracts you the most in that thing?
  • Which is the most embarrassing moment you have ever dealt? How did you come over it and faces the same bunch of people again?
  • Is there any sort of change you want to bring in the thinking process of your family member? It can be related to any tradition, wrong belief or inequality?

Deep Questions To Ask A Guy

Some questions make a place in your heart and mind. It is very important that you show you are interested by asking significant questions to the guy. It is not easy to make boys speak their hearts out and if you want to know him deeply, you will have to ask him the right questions. Starting a conversation is never easy, so here’s a list of deep questions to ask a guy:

  • An idea that changed your life or any decision which was a life-changing experience?
  • There are people who are trying to save toxic relationships and are baring the baggage of past on their shoulder? What makes them do such things according to you?
  • What is the nicest thing or the best compliment someone has ever given to you?
  • When was the first time you developed feelings for any girl? What were the exact feelings?
  • If there any female actor you are fond of and would drop anything to work with her?
  •  Is you has superpowers, what is the one thing you would want to eliminate and add in the world for better living?
  • What is your guilty pleasure?
  •  If you were given million dollars, would you leave everything and settle in abroad?

These sets of questions can serve as a small step to knowing someone. Some of them are too personal but if you align with him properly, he won’t hesitate to answer. He may ask you the same question in return after answering the question, so make sure you are ready with your answers too.

Try to be natural and honest while asking. From these questions, you will gain some comfort and it may open doors for your further conversations. Some questions may cause reactions but make sure you handle them gently. Few of the questions may result into conversations and you both can continue to chat for a long.

You Can Also Check Out:

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