26 Important Questions to Ask A Guy That You Like

questions to ask a guy that you like
Questions To Ask A Guy That You Like

There are important questions to ask a guy that you like or questions to ask a guy who likes you. One of the best ways to build a healthier relationship is by understanding your significant other.

Failing to understand your partner can be frustrating regardless of the level of your relationship. It can lead to emotional turmoil. 

26 Important Questions to Ask A Guy That You Like Share on X

In the worst-case scenario, it can also ruin your emotional intimacy, shaking your bond’s foundation of trust and satisfaction. 

Most men struggle to talk about their feelings. As such, that can further hinder you from knowing your guy deeply. However, asking in-depth, open-ended questions can be the starting point towards validation by each other. 

The questions will help you share your feelings and thoughts freely. As a result, it can elicit genuine intimate responses that can reinforce and deepen your relationship if you so choose to date. They’ll help you: 

  • Create an open communication,
  • Know what he needs in the relationship, 
  • Deepen intimacy and relationship, and 
  • See red flags.

If you haven’t started dating yet and you’re just trying to catch his eye, asking questions can help you understand how to make a guy interested in you. Caring about what he cares about can help keep him invested in the relationship. Besides, it will allow you to nurture a more genuine connection with him. 

But don’t fake it just because you’ve found what’s appealing to him. It will flip everything into poison quickly if he finds out.

So, mix genuine affection and the correct dose of attention, and your man will feel heard and seen by you. 

But, you must first understand him. That’s why I’ve made this list of 26 questions to ask a guy who likes you to help deepen the bond between you. 

26 Questions To Ask A Guy That You Like

questions to ask a guy that you like
Questions To Ask A Guy That You Like
  1. What Do You Expect From a Healthy Relationship? 

The question helps you uncover his expectations of the relationship. You can tweak it a bit to get more insights by enquiring about whom he models his relationship after. You can also follow up the question with what he admires most about his model relationship and if he’s seeing that happening in his current relationship. 

It is quite a load, so be calm and relaxed as you ask it. 

  1. If You Were to Propose, Which Ring Would You Choose? 

Although the question appears as an attempt to understand his taste in jewelry, it goes beyond that. It is a subtle way of knowing whether he is ready to take the relationship to the next level or not. 

Because he will throw the question back at you, you should carefully pick your preferred ring. You will have to validate your choice and its meaning to you and the relationship. 

Diamond goes through intense heat to gain its strength and brilliance. So, it has a significant meaning in love and endurance. That’s why diamond rings should be the best answer. Its sparkling elegance is irresistible. Also, it is durable, so picking it shows that you wish your bond with him to stay brighter and stronger. 


4 Important Things To Consider Before Getting Married

  1. How Did Your Last Relationship End?

You can learn a lot from his past and know whether he can take the relationship to the next level. Understanding why his last relationship ended can help you avoid the same mistakes that hurt the bond. 

If it was a toxic relationship or there are still attachments to his ex, you need to address it ASAP. It is because toxic relationships can have long-term impacts, and you don’t want that to affect your current relationship. 

Be open to this information and process them as objectively as possible. As such, it will help you develop ways of building a relationship that does not fall into old mistakes. 

  1. Who Is the Closest Person in Your Family?

One of the most important questions to ask a guy that you like is his family dynamics.

You can uncover his family dynamics using this question. It will help you know who he feels safest with and why. It can be a subtle way of probing his childhood without being overbearing. 

It may also give you a glimpse into what makes him feel accepted, loved, or a sense of belonging. He may give various reasons for his pick, so listen to them carefully. 

  • Is he closest to his mom because she listens?
  • Is he safe with his sister because she doesn’t dismiss his feelings?

You can emulate the person he is safest with to ensure he is also safe and closest to you. So, if the closest person is the sister who never dismisses his feelings, ensure you do the same. 

  1. Who Do You Count On Most in Your Life?

It is good to know his support pillar when hell breaks loose. So, is it his best friend back in grade school or his uncle? Any person he relies on when things get tough or south will hold a special place in his life. 

It will help you learn about his victories, challenges, regrets, and those who have been there for him.  

  1. What’s Something You Don’t Wish to Do Again? 

Learning about the experiences of your significant other allows you to understand the partner more. It will also let you know what awkward situations to avoid. 

It will also deepen your relationship as it allows you to nurture empathy and have an in-depth understanding of your partner’s character. 

  1. What Do You Love About Your Mom?
questions to ask a guy that you like

Most of us have problems with a mummy’s boy or a misogynist. If you’re one of them, then asking him this question can get you more closure to size him up. Watch out for any overreliance, bitterness, or hurt because they can be red flags. 

However, do not be quick to judge him just because his mother hurts him. But be on alert because it can affect how he treats you, particularly if he struggles to handle it.  

  1. Tell Me More About Your Best Friend?

He may give the same answer as #5. But the person he counts may not necessarily be his best friend. Buckle up if you’re hoping that the answer will be you. It is okay to have best friends outside the relationship. 

The question can help you understand if he is a lone ranger or an extrovert capable of healthy platonic relationships. 

  1. What’s Your Passion Project? 

You need to get as close to his passions as possible. The question allows you to find out what matters most to him and where he spends most of his time. As mentioned in question #4, try and glean what makes him safe and happy. Next, cheer him on and affirm his passion. 

Maybe the past girlfriends or wives dismissed his hobbies. Cheering him up on his passion will build him. You may be interested in his hobbies but try to support him if he means a lot to you. 

But, you should only support his passion, not abandon yours to concentrate on his. 

  1. How Do You Like to Spend Your Time After Work?

The question allows you to gauge how he handles stress. So you must know:

  • Does he prefer to get home and relax on the couch?
  • Does he opt for the gym or a run with the dog after work?

The question will help you understand if he refuels his energy by being with people or as a lone ranger. 

  1. What’s a Secret that Most People Don’t Know About You?

The question will allow him to share something personal. The answer could be funny or tense; regardless, it will lead to self-disclosure that will deepen your intimacy. 

  1. What Makes You Angry?
questions to ask a guy that you like

Sweetheart, you don’t want an angry man in your life so this is one of the most powerful of the questions to ask a guy that you like.

We occasionally get pissed off because people and life can be annoying sometimes. But, if he is quick to anger and blows everything out of proportion, that’s someone to be left alone. 

Excessive anger is a time bomb that can be extremely messy and dangerous even to your own life. So, let the question help guide you on his anger. You can follow up the question with how he manages his anger issues.  

It helps you know whether he can control himself and react to the situation better after calming down. If he can not control himself, then be careful. Alternatively, you can help him adopt a healthy anger management program. 

  1. What Stresses You Out? 

The question will help you walk in his shoes and see his situation from his point of view. You’ll be showing empathy that will, in turn, help you connect on a whole deeper level. 

You can reinforce the question with “What stresses you the most about that?” The answers he gives will help him have a deeper understanding of his stressors at work or in his personal life. As a result, the closure can help you encourage him genuinely. So, you should look for ways of cheering him and being the shoulder he can lean on as he deals with his stressors. 

  1. What’s Your Perfect Day?

The question can be a way to help you understand ways of helping him deal with the stressors you uncover in question #13. It is common for guys to plan for movie dates and other fun activities. The answers to this question can help you level up your game too. 

It can help you show him that you’re listening to him. As such, you can create an incredible ideal date theme around his answer. 

Using that approach will demonstrate to him that you’re not too dependent on him for your happiness. 

  1. What Is Your Most Significant Life Achievement?

It is okay to brag a little. So give the man some space to show what he got. It will give you a glimpse of what he values in life. Go ahead and ask him about the feeling after his accomplishment. 

Another perfect follow-up inquiry is on tracking what his target is for now. Whether his goals are lofty or solid to you, try to show support for what he believes in. 

  1. What’s the Most Unforgiveable Thing to You? 

Some unforgivable acts can be relationship dealbreakers. The question will help you probe what his dealbreakers are. It is essential because it can help you ensure it does not mess with your own dealbreakers. 

And if you can stretch the talk to help you agree on the common ground on what’s unforgivable or not. That closure can reinforce your bond because you will know which boundaries not to cross. 

Questions To Ask A Guy Who Likes You

  1. What About Our Relationship Makes You Happy?

The question can help you know some of the things your partner appreciates about you. That can be a great anchor for your relationship. Plus, regular affirmations and communication about what both of you appreciate about one another can help reinforce your relationship. 

  1. What Is the Difference Between Us That You Find Attractive and Love?
questions to ask a guy that you like
Questions To Ask A Guy That You Like

Is it true that opposites attract? In magnetics – yes; in relationships – occasionally. However, having palpable differences is intriguing, piques interest, and can spark attraction. That can be a great foundation for sustainable and strong foundation for strong relationships. 

So, go ahead can explore some positive feedback on unapologetically being yourself. 

  1. What’s One Thing You Wish Us to Do That We’ve Never Done Before?

This one is best suited for those thinking long-term about their relationship. So, can you vision and may be manifest it together? It is okay to share some experiences. So whether it is an open mic duet for the karaoke night, marathon, or even as bold as buying real estate, it is okay to envision it. 

It is even better to openly express it to your significant other and gauge his thoughts. 

  1. If You Were to Change Something About Our Relationship, What Would it Be?

Let’s face it; it would be unnerving to ask such a question if you’re cool with how things are. Whether you are cool with it or not, the question can help make him comfortable and nudge him to talk about some issues that have been on his mind. 

Process the answer carefully and understand his concerns. You can work on his concerns to help deepen your bond. 

  1. What’s My Best Non-Physical Quality You Find Attractive?

The initial stages of most relationships are entirely based on physical features. But, with time, he will lose interest in the irresistible features that initially attracted him. But, it does not apply to all men. 

But that’s the nature of most men – pursue you to insane lengths with great gifts and sweet nothings. Only to dump you for another younger girl. It can be hard to understand them. But the question can give you vital closure on what keeps him attracted to you apart from the physical features. 

In fact, every strong relationship goes beyond physical features. So, it could be a way of gauging the strength of his commitment. There is nothing as refreshing as hearing what fuels attraction beyond your looks. 

  1. What’s Your Biggest Fear for Our Relationship?

Relationship anxiety can quickly ruin something so great with all its future promises. Therefore, you must address relationship anxiety and cope with it whenever you feel it creeping in. 

It is significantly tied to past experiences, and they can easily dissipate when aired out and shared. So, asking him this question can help both of you address past experiences and fears to avoid ruining your beautiful bond. 

  1. Can We Talk About Our Health Histories? 

It is absolutely important to know each other’s health histories. If you’re yet to get sexually active with your partner, you should know if he has STD or anything that can affect you. 

As the relationship matures, you also need to understand other medical aspects like mental health. You should also talk about genetic diseases that can affect any kids you may have. It will help you know when and how to involve medical counseling and treatment in your relationship. 

Without medical history, your relationship may not move to the next level. For example, you may need to know if both of you have a genetic condition that can terminally affect your unborn baby.

You wouldn’t want to want to take health related issues lightly especially if you think you both have a chance at being life time partners so this relationship question is one of the most important questions to ask a guy that you like.

  1. What Is It That You Cannot Change in Your Life for Someone, Even Me?

The question can have negative undertones from a glance. However, knowing your significant other’s non-negotiable attributes and habits will help you understand what’s so dear to them. You can adjust to them to help deepen your bonds. 

  1. What Do I Mean to You?

Most men don’t like this question, especially if they feel you’re pressing them to commit so fast. Although it is easy to shy from it, a time reaches when you must ask hard, deep questions like this. 

If you feel you’re at that level in your relationship, go ahead and get closure on what you mean to him. It can help reinforce your love if he confesses how dear you are to him. 

  1. What Are Your Political Ideals 
questions to ask a guy that you like
Questions To Ask A Guy That You Like

Finally, his political views and ideals. Well, this can get extra heated. But, it is good to know his political ideals to check if you’re comfortable with them. 

I don’t know about you but my man’s political views matters to me and it should matter to any woman so it should definitely be one of the crucial questions to ask a guy that you like.

Although minor disagreements are welcome and healthy, you should avoid ongoing tension. It can break the foundation of your relationship. 

Despite the disagreements, you may have more in common than superficial politics above party affiliations and policy views. The tolerance you can create using the question can further help deepen your bond.  

Hey, if you would also like to read about more relationship questions you can ask your spouse to deepen intimacy and bond, check some super cool ones below!

207 Deep Questions To Ask Your Boyfriend To Get To Know Him Better

101 Conversation Starters To Break The Ice And Know People Better

9 Deep Relationship Questions That Will Transform Your Relationship

How To Rekindle Love And Bring Back The Spark In Your Relationship

195 Relationship Questions To Ask Guys

Final Thoughts On Questions To Ask A Guy That You Like

It is okay to ask questions and these questions to ask a guy who that you like are powerful and also important to help you better understand who he is and his views about issues that matter to you.

The only way of knowing is by asking. If you’re afraid to ask, you may never know whether your significant other truly loves you or even plans to take the relationship to the next level. So, open communication can help strengthen your bond as it helps address certain issues that may be swept under the rag. 

It will help you to know each other better, deepen intimacy and even uncover red flags if any. 

But, do not turn these questions into an interview. Also, avoid criticism of serious answers as it may lead to tension and make him withdraw from you. Plus, pay attention to non-verbal cues to reinforce his message. 

If done right, these questions can help you know your partner better and understand what he needs from


questions to ask a guy that you like
Questions To Ask A Guy That You Like

Kinging Queen

Jennifer Pompaski
Jennifer Pompaski

Hi, my name is Jennifer. I am an Engineer by day and a blogger 24/7. I am passionate about Self Improvement & Productivity and this blog is dedicated to that passion! I hope you find it worthwhile each time you visit! If you do find anything helpful on here, kindly share because sharing is caring!

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