25 Questions To Ask A Guy To Know His True Intentions

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What are some questions to ask a guy to know his true intentions without saying, “Chris, what are your intentions with me?”

When you meet a new man and have a great connection, it’s natural to wonder where he stands emotionally.

Does he like me, or am I imagining it?

Does he see this going somewhere in the future, or is it more of a good enough for now situation?

If you are looking for a long-term relationship, you want to know sooner rather than later if he wants the same thing. Your time is too precious to waste on a dead-end fling. Summer flings are great, but you’ve got romance novels to indulge in those, and you’re looking for the real deal.

That’s why I’ve compiled a list of essential questions to ask a man so you can figure out what his true intentions are without having to directly ask him what his intentions are and risk scaring him away.

Questions To Ask A Guy To Know His True Intentions (If You Just Started Dating)

1. What do you like and dislike about dating?

This question will help you dig up dirt on how this man views the dating experience. Is he the kind of man who feels bitter and resentful because he hasn’t found his perfect mate yet, or does he have a positive outlook and view each new date as an opportunity to get to know someone new? His likes and dislikes about dating will show you what’s important to him when dating and what he’s ultimately looking for.

2. Do you like being single?

You can enjoy being single and be open to finding a relationship simultaneously. This is all about seeing how comfortable he is within and how desperate he is on a scale of 1-10 to couple up. The sweet spot is a man who is content being single but equally wants to find someone to share his life with. Someone who enjoys cuddles and takeout on the sofa as much as bar hopping on a Saturday night. Someone who loves boy’s night as much as date night.

3. What do you think about casual dating and hookups?

man and woman on a date

One of the many great questions to ask a guy to know his true intentions. Of course, he might lie to you, so remember to listen to what he says, but pay closer attention to his actions. If he tells you he isn’t into hookups and then invites you back to his place on the first date, he’s probably telling porkies.

4. Have you ever ghosted anyone?

Can you trust a man who has ghosted someone else in the past?

There are three possible answers to this question:

  1. “No, I’ve never ghosted anyone,” when the truth is he ghosted a woman last month. This man is a liar and doesn’t have the courage to own up to his mistakes. Time to say, NEXT!
  2. “Yes, I have ghosted women in the past, and I’m not proud of it.” A much better response because although what he did isn’t great; he’s taking accountability for his actions.
  3. “No, I’ve never ghosted anyone,” and he’s telling you the truth because he’s a super decent man who would never think of doing such a thing. You’ve got a rare gem on your hands here.

5. What do your friends say about your dating life?

Our friends and family can often spot patterns and themes in our lives that we are oblivious to. This question will help you understand the difference between how he thinks his dating life is going versus what his friends think about his dating life. Does he have a reputation for falling too quickly or jumping from one relationship to the next without taking a breath? All great clues to give you more insight into how he ticks and what his intentions are with you.

6. Where do you see yourself in 5 years?

Does he see marriage and kids in his future? Does he plan on moving cities or continents? Or does he want to start a business or grow an existing one?

This is one of the best questions to ask a guy to know his true intentions because it will help you determine whether you share the same life values. If he sees himself quitting his job and traveling the world in a hot air balloon over the next five years, it’s unlikely he sees this developing into a long-term relationship unless he’s planning on you joining him.

7. How would you describe your ideal partner?

When put on the spot with this question, it’s hard for a man to lie about what he is truly looking for in a woman – the truth will naturally come out. Pay attention to what he says and whether his ideal woman matches your personality and lifestyle.

For example, if he says his dream woman is a stay-at-home Martha Stewart type (minus the jail time), but you’re a go-getter career woman who loves her job, it’s probably not going to work out. He wants home-cooked chicken casseroles simmering on the stove for him when he returns home from work, to which you might laugh out loud and say you were hoping for the same thing from him!

8. Are you dating any other women?

man and woman talking

In my Love Accelerator coaching program, I emphasize to women that until you have explicitly had the talk where you both decide to be in an exclusive relationship, assume you are single. And if you’re single, you should continue to date other people and qualify your options (I call this Little Love Step #4). So if you haven’t done that yet, he should be dating other women – a high-value man will be dating other women at this stage.

9. What are your feelings about long-term relationships?

Has he ever had a long-term relationship before (hopefully, he has)? Does he enjoy being in a relationship? What does he enjoy most about it, and does this align with what you love too?

Beware of any man who says he isn’t into labels or thinks marriage is a scam. While it’s perfectly fine not to want to get married, comments like these usually only come from commitment-phobes.

10. Are you looking for a serious commitment right now?

This is a more direct way of finding out whether he is currently looking for something serious or if he’s looking for sex. Most men will be honest with you.

If he tells you, “I’m not ready for a relationship right now,” don’t take that as code for “the right woman would make me want to be in a relationship.” It’s not. It’s him being honest with you about what he’s able to give you (and not give you). If he says he is looking for something long-term, then you have a more solid idea of his true intentions.

11. What’s your number one priority in life?

We all have numerous parts of our lives to juggle (work, family, friends, health, hobbies, spirituality, etc.), and there will be periods where we are required to devote more energy to one of these areas than the other. That’s life. But this question will help you see if he generally prioritizes relationships and family or if his job or personal ambitions always come first. An excellent follow-up question is to ask him why.

12. What’s your biggest goal?

His current goals will inevitably have an impact on you. Let’s say you’re dating a tech entrepreneur who is currently building the next Facebook – this is bound to impact his ability to commit to a relationship with you and will affect the lifestyle you can lead as a couple. He might regularly be pulling 18-hour days and sleeping in his office multiple nights a week while you’re looking for a man who has time to whisk you off to the ballet after work and leisurely brunch on coffee and croissants with you in Paris.

13. Are any of your friends coupled up?

This is one of the top questions to ask a guy to know his true intentions with you because it gives you a great idea of his current lifestyle and the influences he has around him.

If all his friends are currently single and living in apartments together where they throw wild parties that regularly run through to 5 AM and get shut down by the police, he might not be in the headspace for a relationship. But if most of his friends are coupled up, living with their partners, married, or have kids, he’ll see how happy they are, which is likely to make him want that.

14. How many dates should people go on before sleeping together?

questions to ask a guy to know his intentions

Another great question to gauge whether he’s looking for something casual or more serious. The more eager he is to jump into bed, the more likely he is to be looking for something casual.

If you want to know more about how many dates to wait before having sex with a man, check out this article.

Questions To Ask A Guy To Know His True Intentions (After You’ve Been On 5-10 Dates)

1. What’s the longest relationship you’ve ever been in?

This is how to ask someone what their intentions are without being so direct about it. His answer to this question will give you insight into whether he knows what a healthy relationship looks like, whether he is emotionally mature, and whether he’s boyfriend material. If he has consistently struggled to make things last longer than three months, he’s either ridiculously picky or doing something that makes women drop him like a hot pop tart.

2. Have you ever been in love?

Like the previous question, this will give you insight into how quickly he falls in love and how many times he has fallen. Has he ever been in love? Did he think he was in love, but looking back now with wisdom, he doesn’t believe it was the real deal? His answer will tell you if he’s open to finding love and ready for it.

3. Tell me about your last serious relationship?

This is up there on important questions to ask a guy to know his true intentions and where his head is.

How long ago was his last breakup?

If it was sooner than six months ago, his ex might still be on his mind. Was he married, and is he divorced yet?

If not, don’t get involved.

How long did the relationship last?

If it spanned years, then you know he’s able to be in a committed relationship.

4. Why did you break up?

This is a great follow on question from the one above. Who broke up with who, or was it mutual? How does he speak about his ex? With kindness or with bitterness and blame? A man ready to be in a healthy, long-term relationship will be aware of his flaws and take shared responsibility for his failed relationships.

This question will give you insight into his quirks, flaws, and psyche and shed light on any potential deal-breakers or issues that may affect your relationship with him.

5. What do you think is the best part about being in a relationship?

What to ask a guy to know if he's serious?

How does he feel about being in a relationship, and what does he value? Is a relationship attractive to him because he’s looking for a beautiful woman to parade on his arm at charity events who will also iron his shirts? Or is the best part for him having someone who is always on his team, cheering him on, and loving him even when he’s sick in bed and hasn’t showered for three days?

6. Do you have any reservations about being in a serious relationship?

You’re giving him a golden opportunity to come clean if he has any hangups about committing to you long-term. The answer you’re looking for here is no. But if he had a terrible breakup, it’s okay if he’s afraid of getting hurt again, as long as he isn’t allowing that fear to control his life.

7. What does cheating mean to you?

This is one of those questions to ask a guy that will give you a better sense of his moral code and boundaries, which directly affects his true intentions with you.

Some people have different ideas of what cheating means.

Are you cheating if you’re working out at the gym and notice someone you find attractive? Are you cheating if you flirt with a cute stranger in a bar? How about if you occasionally fantasize about someone else while having sex?

If he thinks that having sex with other women on a different continent doesn’t count as cheating, that’s your cue to leave.

8. When do you think someone is ready to get married?

This isn’t the most subtle of questions, but if marriage is important to you, it’s a great one to ask. If he gives you a certain age, think about where he is in relation to that age and whether that timeline feels good. Most people in the U.S get married between 25 and 30. If he’s in his forties and beyond, there’s a good chance he is divorced and may or may not want to get married again. But it’s better to find out now rather than invest a lot in this man only to find out months later that he refuses to walk down the aisle again.

9. Do you see yourself having kids?

Is he a dad already? If he is, does he want more kids, or does he have his handful with five already? If he isn’t, does he see kids in his future, or is he content with his life the way it is now?

There’s no right or wrong answer to this question; what matters is that you are on the same page. If your cats are more than enough company for you, but he has always dreamed of having a mini soccer team, he doesn’t match your love vision (Little Love Step #2).

10. How do you feel about the time we’ve been spending together?

how to ask a guy about his intentions

Is he enjoying spending time with you? Is he having fun? Or does he not have much to say about it, or worse, is he avoiding answering the question? This is how to ask him what his intentions are in a light-hearted way. Yes, you’re putting him on the spot a little here, but once you’ve been on more than five dates with a man, your relationship should organically be developing, and this is a natural question to ask.

11. Where do you see this going in the future?

Wondering how to ask a man what he wants? The final question on my list is to go the direct route and ask him where he sees the relationship progressing. This is the best approach if he often avoids talking about the future because there’s no way to dodge this one. Either he tells you where he sees things going, or he says he doesn’t know, and that in itself is an answer because indecision is a decision.

Are You Ready To Define Your Relationship?

Once you know his true intentions, you might be ready to define your relationship. This is what I call Little love step #6.

Avoid asking him, “what are we?” because this gives your power away to him!

Likewise, don’t avoid talking about the future altogether and pray that he will one day bring it up or assume that he must be on the same page as you – he might be on a different planet.

Follow the three Rs:

  1. Tell him you’re looking for something real – you’re not looking for something casual.
  2. Reassure him that you like him – men need to know you like them.
  3. Redefine the current relationship – what does he want, and does this match what you want?

Don’t stop dating other guys until you’ve had this chat and have explicitly defined the relationship. Until you do this, you are both single and free to date other people.


Have you ever asked a guy one of these questions to know his true intentions? What happened? Tell me about it in the comments below!

Editor’s note: Ready to attract love with a proven strategy? Watch this free video to learn the 7 powerful steps

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1 year ago

I have been with someone for 5 years hes not loving with me even in bed hes selfish and drinks alot I have tried to work it out it feels only one sided hes committed but does things like goes to sleep because he’s had to much to drink no sex and he’s very vanilla I was married for 35 years and divorced as of a few months ago I think it was probably the worst mistake leaving my x for this man, he has a really bad temper fights with his kids im tired of it and have told… Read more »

1 year ago

My husband passed away from Alzheimer’s after 56 years of marriage. He was an awesome husband and father. I met him in Highschool, had zero dating experience with others. I met a gentleman before my husband passed away whose wife was in the same memory care. Two years after my husband died the gentleman and I started having dinner together. I often cooked but rarely we would go out. Eventually my new friend confessed he was sexually drawn to me. His wife was still alive but could no longer walk or communicate. I agreed to a relationship. His caveat was… Read more »

9 months ago

I feel your pain. I was in a 28 year relationship and after it was over, I met a man who I emotionally fell for. Not love but I just can’t get him out of my head…AAAHHHH!!! He didn’t want a commitment which I was fine with as I just got out of a 28 year marriage and didn’t want a commitment. He says one thing, but does another. I know I should be saying “NEXT” but there’s something about him. Oh, that would be the challenge. LOL He cancelled our date for today, so this morning I told him… Read more »

3 months ago

how are you doing today i also lost my wife 10 years ago i am looking for a good woman that i will care for and also make my dreams come true.

1 year ago

I have used a few of these questions after reconnecting with a man I hadn’t seen in at least 25 years. We discovered that we both wanted more than to be just friends all those years ago, but never knew because we had not communicated openly with each other about what we truly wanted. Now that we are in our 50’s and have kicked ourselves for years waisted perhaps with the wrong people, we are trying hard to communicate, be open, and not miss out on anymore. The questions about his past relationships, the length of them, why it ended… Read more »

1 year ago

I met the most amazing gentleman, and everything aligned like we were best friends and have known each other for years. To be honest, and I told him that he is the first man since my divorce 15 years ago who I could truly say, “I love you” to with true commitment. He also felt the same way. He is also very in touch with his feelings and we could truly open up to each other. Then he had some heavy stress going on with one of his adult children, which I supported him. Then I had and have a… Read more »

1 year ago

The above video on a man falling in love with a woman was perfectly on target with the gentleman I was dating. Am I wrong to seek him out again when my life stabilizes, as I truly believe we were met to be together, which he also repeatedly stated. He also repeatedly talked about seeing me in his future, and I saw him in mine. I am an Aries by nature and I have always gone after what I want, but don’t want my assertion to ruin a possibly good thing that means so much to me.

Nelda Johnson
1 year ago

I am an older lady beginning to date after 23+ years. I asked my gentlemen your question about cheating–perfect question–we definitely have different views-it gave me a chance to share my thoughts–and I learned, based on my definition, how much he cheated on his wife, who by the way is deceased. something to cogitate!!

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3 months ago

I asked these questions to my boyfriend, and now he is my husband

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