You met a charming guy, went on a couple of dates, you had your first kiss with him, and now the butterflies in your stomach can’t wait to take things to the next level. But, wait. Do you know him well enough to be vulnerable with him and open your heart? If you don’t, then these questions to ask a guy to know his intentions will help you in finding whether he is on the same page as you. 

You can’t just directly ask about a guy’s intentions because that will make you look desperate. It will convey the wrong message. You need to learn how to ask a guy what his intentions are regarding you without being direct. You have to be subtle and gentle with your questions. We will tell you how you can do it nonchalantly.

When Is The Right Time To Ask A Guy About His Intentions? 

The timing for discussing a man’s true intentions with you usually depends on three things:

  • The comfort level you share with him 
  • Which dating stage you are in at the moment 
  • The nature of your relationship. For example: friends with benefits, polygamy, or sharing an intimate, emotional connection

It’s crucial to keep the above three things in mind because pushing the conversation too early can be overwhelming for the other party if it’s just a casual fling for him. They may see this as a talking stage red flag and pull away from you. 

So, we have come up with a guide that will help you understand when is the right time to ask a guy what he wants from you: 

  • Establish trust and connection before confronting a guy about his intentions
  • Allow time for both of you to feel comfortable opening up about personal aspects of your lives
  • Think whether you have achieved any significant relationship milestones like becoming exclusive, meeting each other’s friends and family, or introducing each other as their special someone on social media platforms 
  • Be attuned to his cues and signals. For example, if he has expressed a genuine interest in getting to know you on a deeper level, it signifies a readiness for a conversation about intentions
  • Don’t rush into conversations surrounding intentions, serious commitment, and relationship goals 

Should you ask a man what his intentions are? Yes, but only after assessing some external factors like work commitments, family emergencies, and personal problems. You can’t ask him these questions when he is feeling low or stuck in a career crisis.

Now that you know where you stand in his life and the right time to ask these questions, read along and find out all the important and deep questions to ask a guy to know his intentions. 

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What Questions To Ask A Guy To Know His Intentions 

It’s essential to have such deep conversations with your potential partner because such openness will foster an environment where both can be genuine with each other. We present to you all the questions that fall under the two most important categories of dating: early and when you’ve known him for a while.

Questions To Ask At The Early Stages Of Dating

You have to mind your P’s and Q’s when you are trying to ask a guy what he wants from you during the early stages of dating. Anything you say or ask could offend him since you don’t know him well yet. Listed below are some questions you can ask a guy when dating casually: 

1. How do you like to spend your weekends? 

This is one of the most random yet the most important questions to assess compatibility between partners. What does he like to do on weekends? Is he a couch potato or does he like to go out and shake it up a little?

It’s crucial because it will help you determine how much fun you are going to have with him. If you are the kind of person who likes to Netflix and chill on weekends, then you wouldn’t be compatible with a man who is a frequent partygoer.

If reports are to be believed, that’s the reason Joe Jonas divorced Sophie Turner. She liked to party a lot and he liked to stay at home. Yeah. That’s why you must find out how he likes spending time on his day off so things don’t become complicated down the lane. 

2. What is your preferred way of communication? 

Texting, calling, FaceTiming, or meeting face to face and discussing things in person? This is one of the questions to ask a guy if you want to have a serious relationship with him. It sets the tone for a successful relationship

If the two of you hate being on call for long hours, then WhatsApp will become your messiah. If you are worried about being catfished, then you can ask him if he wants to FaceTime with you instead of texting. It’s a simple question but it will help the two of you head in the same direction and bring you closer. 

3. How do you handle stress? 

Stress is one of the emotions humans go through frequently. What’s important here is how he is equipped to handle that stress.

Does he fall into a rabbit hole and start overthinking? Some people start drinking, whereas some start emotional eating. None of these things are considered healthy. 

“It’s cardinal to date a partner who knows how to handle stress because the art of being a partner is closely related to managing the stress of never quite knowing for sure what comes next”, writes a Quora user.

So, if he indulges in positive self-talk, exercising, and meditation, then he is a man with good coping mechanisms. 

4. Are you an introvert or an extrovert? 

There’s nothing wrong with being an extrovert or an introvert. However, if you are an introvert and want to be with someone just like you, then you need to find out before getting into a committed relationship.

Sometimes, opposites attract. So, you never know until you find out what type of men you are into. 

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5. What are your hobbies and interests? 

Your interests don’t need to match with your potential partner’s interests. But it’s nice to make movie nights a sacred tradition or eat croissants every Sunday. There should be at least a few things that you and your partner bond over.

Let me give you a personal example. I am a writer and my partner is a banker. He doesn’t read and doesn’t understand the significance of words in my life. I don’t understand numbers. We don’t bond over work but we bond over our love for food and trying new restaurants.

Ask this question on your first date and see if the two of you can find a middle ground to connect that will help you establish an irresistible emotional connection

questions to ask a guy to know his intentions
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6. Do you go on “first dates” often? 

This is a very sly thing but if you do it correctly, he won’t get offended and will pass it off as a joke. This particular question will help you have a better sense of his dating life. Is he a serial dater?

He can date as many women as he wants but if that’s something you don’t like in men, then ask him this question to have a better understanding of his love life.

What if he is just seeking the thrill and not the actual relationship? Ask him about his experience in online dating too. This will help you shed light on his intentions and you can decide whether you want to continue dating this man or not. 

7. When did your last relationship end? 

Some people say that it’s a bad idea to ask about past relationships. That’s an old-school thought. In today’s times, everything has to be straightforward because you don’t want to bear the brunt of your past relationships.

Find out if he is over his ex-girlfriends and whether he has moved on or not. This question will also let you know if he is using you as a rebound to forget his ex.

If he answers this question, then you can smoothly ask why the relationship ended. But don’t make it look like you are scrutinizing his personal life. Perhaps you can share your breakup details to earn his trust. 

8. What’s one value you desire in a partner? 

When you reach a certain age, there are a few qualities you can’t compromise on when looking for a partner. What’s that quality for him? Is it altruism? Respectful nature, beauty, honesty, forgiveness, or open communication?

It’s a good sign if he opens up and answers this question. You can implement and execute that quality in yourself and make him fall in love with you. You can also keep the conversation going by finding out what his core values are in a relationship. 

9. Do you have any habits or quirks you wish you didn’t?

There are many good and bad personality quirks inside each human being. Some like to be dominant in relationships and some people have this bad habit of giving their partner the silent treatment after a fight.

That’s why this question is a must-ask when you are in the early stages of dating. It will help you understand your new partner on a deeper level and how to handle them during conflicts. 

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10. What kind of challenges have you overcome in life? 

Is he a quitter or a problem-solver? I used to be a quitter until I met my partner. The answer to this question will prepare you for the future. Do you have to be strong for the both of you when there are tough times or is he strong enough to deal with his problem smartly?

If you are serious about him, you can become a pillar of support for him when he is going through turbulent times. 

11. How important is mental health for you? 

Good mental health is crucial for overall well-being and quality of life. It enables individuals to cope with life’s challenges, setbacks, and stressors more effectively. It also helps foster emotional resilience in people.

On the contrary, if someone’s mental health is not in the right space, then it can be very difficult for them to manage things daily. Hence, it’s of utmost importance that you date a man who knows how to treat you when you are having a gloomy day. 

Questions To Ask When You’ve Been Together For A While 

How to ask a guy what his intentions are if the two of you have been together for a while but you still aren’t sure of his intentions? Don’t worry. These questions will help clear the air in your head and will bring clarity to your relationship. 

12. What is your love language? 

The hallmark of every good relationship is to make your partner feel valued and loved. When you tailor your expressions of love to your partner’s specific preferences in serious relationships, it deepens the emotional connection between you and builds a stronger bond. It will enhance intimacy and prevent partners from drifting away from one another. 

Ask a guy what makes him feel like he is loved. Is it gifts, spending time together, words of affirmation, touch, or acts of service? By learning how he likes to be loved, you will understand him better and there will be fewer conflicts. 

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13. How many long-term relationships have you been in? 

Ask him about his previous relationships to get a better understanding of his love life. What was his longest relationship? What went wrong? What were the problems?

It will help you understand all his traumas and insecurities. You can also talk about his childhood issues, without offending him and judging if he is ready for that kind of a conversation.

You can also open up and talk about your past experiences with him as well. It will be a good bonding exercise. If you both are willing to share such vulnerable details, it means you’ve built the foundation of trust with him. 

How to know a guy's intentions for you
Image by Freepik

14. Are you comfortable discussing finances in the relationship? 

One relationship is different from the other. Not everyone openly discusses their finances even when they are married. But if you want complete transparency, ask him if he will be open to discussing the money aspect.

Similarly, you should place your cards on the table and tell him about your savings and investments. This shouldn’t be one-sided. 

15. How important is personal growth for you while being in a relationship? 

Personal growth is paramount in a relationship as it not only encourages individual well-being but also contributes to the overall health and success of the partnership. You can’t lose your individuality just because you are in a casual relationship.

Most women lose their identity when they are in love but they forget that you need to continuously evolve, gain self-awareness, and hone emotional intelligence for their good.

Ask your partner if he wants two peas in a pod like a yes-man or someone bold enough to contradict his opinions when the situation demands. 

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16. What is your perspective on privacy and boundaries? 

Partners need to have privacy in a relationship. Therefore, if you’ve been dating for a while, you need to establish healthy dating boundaries. Ask his perspective on it and come up with some ground rules to have a better understanding of each other’s needs.

This is one of the questions to ask a guy to find out his intentions. 

17. If you could make three wishes, what would they be? 

No, you’re not a genie to grant these wishes but he will tell you all about his deepest desires. Is it self-improvement to become more kind? Is it to travel the world or become the richest man on earth? Or does he wish to marry his ideal woman and live a simple life?

His wishes can tell you about the kind of personality he has. You don’t have to be judgmental about it though. To each their own, right? Share your wishes with him and attract love from each other. 

18. What is your approach to intimacy? 

If he expresses interest in having an intimate relationship with you, then you need to ask this question. How will he approach both emotional and physical intimacy? Will it all be about him or will he fulfill your needs too?

Will he validate your feelings? Will he satisfy you in bed? What is his approach going to be? Talk about all these things before you decide to enter into a long-term relationship with him. 

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19. What’s your definition of love? 

Love is complex. It’s multi-faceted. For some people, love is being understood by their partner and when their partner takes responsibility for their well-being.

For others, it is characterized by deep feelings of care, sincerity, and respect. What’s his definition of love? The answer will show you the way to his heart.

Does he want someone who will support his career aspirations? Or does he want someone who will love him for all his flaws and weaknesses? Someone who won’t ask him to change himself. 

20. When do you want me to introduce you to my family and vice versa? 

A guy’s true intentions don’t lie in his body language. It shows when he introduces you to his friends and family members. If he is still hesitant to introduce you to his inner circle after being together for more than six months, you need to question the guy’s intention.

It raises a lot of questions and creates doubt between partners. If he is serious about you, then what is stopping him from having a dinner party with all his special people under one roof? Notice his expressions when you bring this topic up and you will know if he is a red flag or not. 

21. What is your relationship dealbreaker? 

Is it infidelity? Any kind of abuse, financial irresponsibility, selfishness, being clingy, lack of aspiration, or a mismatch in sex drive? It’s crucial to find out which act will be the end of your relationship, especially if you are head over heels in love with him.

22. Can you share your thoughts on starting a family one day? 

How do you know a guy’s true intentions? By asking him about serious things like moving together, marriage, and having one or more kids down the lane. The “where is this going?” questions have become boring now. So try this one and let him face his own feelings. 

Also, clarify that things like kids and marriage don’t need to happen immediately and that you are talking about the future here. Just his word of assurance is enough to get you going. 

The process of asking these questions not only facilitates open communication but also establishes a foundation of trust and understanding. It is through these conversations that a strong framework for mutual respect, shared objectives, and a deeper emotional connection is cultivated as it will ensure that your journey ahead will be aligned and in agreement with each other. 


1. How soon is too soon to ask a guy about his intentions?

It’s way too soon to ask if it’s just your first date. It is also very soon if you’ve never met each other or if you still aren’t comfortable with one another.

2. Can I ask these questions if we are casually dating?

Yes. You can ask the above-listed questions if you are casually dating because they are also a great way to get to know your partner.

3. What should I do if he refuses to answer my questions?

If he wants to avoid talking about these things, don’t take it personally. He is under no obligation to answer your questions if this is just a casual relationship. However, if it’s a serious relationship, then you need to get to the bottom of it. Don’t coerce him but try to talk to him when he is in a good mood and find out what’s stopping him from answering your questions.