23 important questions to ask a guy to know his real intentions

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Want to know whether he’s interested in dating you or just your friend?

Here are 23 questions to ask a guy to discern whether the feelings are mutual. It can be hard to tell where the relationship is going when it feels like there are no solid lines to define. 

The most important thing is that you know what he wants so you can make decisions accordingly and not waste your time with someone who isn’t right for you.

Let’s dive in.

1) Are you looking for something serious?

Does he want something casual, or is he hoping for something more serious? 

The answer to this question will vary from person to person. In general, a plan for the future is what most people want if they’re looking for something more serious. 

If it’s someone who wants something casual and short-term, then he might not be interested in talking about a long-term commitment or anything that could lead up to one.

2) How long do you want to wait before seeing each other again?

Everyone has different thoughts about how quickly a relationship should progress.

If you’re both looking for something serious, then most people like to take things slow since there’s a lot at stake. 

If he wants something casual and short-term, then in engaging in long-term plans or waiting around for you. He might just want to enjoy the time together and go with the flow of things.

3) Where do you see the relationship going?

This is another question that will vary from person to person depending on what he wants out of it. 

While most people hope for a future together, some men who are looking for casual relationships may not have any intentions of dating someone seriously or committing to anyone at all.

If he wants something more serious, then this should come up in your conversation so that you can plan accordingly and not waste your time.

4) How would you describe what we have?

This is a great question to ask at any point during the relationship.

The answer to this question will help you determine whether you’re on the same page about what’s going on between the two of you. 

For example, if he says that you’re just friends, then it’s likely that he doesn’t want a romantic relationship with you. 

If he says that you’re dating, but he doesn’t want anything serious, then it’s possible that he still wants something casual or short-term.

5) What kind of things do we have in common?

If he likes all of the same things as you, then there might be some potential for a future together. 

If not, then it’s likely that he’ll stop wanting to date you after only a few months or so. 

This is because if someone does not have common interests with their partner (things they enjoy doing and seeing), this can lead to an unhappy relationship over time where both people are giving up on what they want in order to change who they are just so that their significant other will stay interested longer than before.

6) How would you describe your ideal partner?

This is another question that’s better asked at the beginning of the relationship when you’re trying to get an idea of what he wants from his ideal woman.

 It may seem like a silly question, but it can give you an idea of what kind of woman he thinks is attractive and whether she matches up with your own personality and characteristics. 

If his ideal woman doesn’t match up with who you are, then it might not be worth pursuing anything other than just a short-term fling with him.

7) How would you describe your ideal woman?

This is another important question for finding out what kind of woman he wants for his future wife or long-term girlfriend.

For example, if he says that she should be a brunette with blue eyes, then you might want to ask yourself if you fit that description.

If you don’t, then it may be better not to move forward with him because it’s unlikely that he’s going to want to date someone who doesn’t fit his ideal.

8) How would you describe your relationship with your parents?

You can tell a lot about a man by the way he treats his family.

This is an extremely important question for finding out how well he gets along with his parents and whether or not he’ll be good boyfriend material.

You don’t want to choose someone who has a difficult relationship with his parents because it’s likely that he’ll have a difficult relationship with you and that his family values aren’t where you would want them to be!

9) How would you describe your relationship with your friends?

This is important because you’re gauging his priorities.

A guy who’s too into his friends is going to spell disaster for you because you’re going to have to fight to spend time with him.

Also, if his friends are not the greatest role models, i.e he’s part of a bad crowd, chances are, you’ll not want to hang around because he will likely be dealing in some dodgy things.

Remember, birds of a feather flock together.

10) Do you think we should take our relationship to the next level?

This is an important question to ask because if the answer is that neither one of you thinks it’s a good idea, then you should probably just remain friends.

If he says that he does want to take things to the next level, then it means that you’re really special and important. It also tells him how much he cares about you. 

You might have a great future together with this guy if your relationship becomes more than just friends. If he mumbles, fumbles, and cannot give you a direct answer, know that he’s not seriously considering you as his long-term girlfriend.

11) What do you think about us being exclusive?

A lot of guys are scared to commit to one person because they don’t want to lose their freedom or have someone constantly nagging at them. 

You need to ask him this question so you can see if he’s willing to commit to you and if it’s a good idea for you two to be exclusive.

Also, you don’t want to be in an open relationship and if does, it’s a complete clash of values.

If he’s not wanting exclusivity with you, spare yourself the heartache and let live and let die.

12) Would it bother you if I go out with my friends?

Friends are a big part of life and they’re going to want to spend time with you, even if you’re in a relationship.

You need to know if he has a problem with you going out with your friends and having a good time. 

If he’s going to be jealous and controlling, then it’s not worth moving in with him because that’s not the kind of relationship you want.

13) If I go out without you, will you go out without me?

If he says that he will, then it means that he trusts you and trusts that you’ll be safe when you’re out by yourself.

It also means that he’s secure enough in the relationship so that he doesn’t feel like he has to control everything about it.

A guy who won’t leave you alone for a moment is a red flag. He’s probably got serious trust issues and you really don’t need that type of negativity in your life.

14) What are your thoughts on cheating?

This is a tough yet interesting question to ask.

If he’s completely anti-cheating, you can rest assured that he’s a keeper and is definitely boyfriend material.

If he’s on the fence or tries to justify under what circumstances he would cheat, he’s got some questionable morals.

Keep him at an arm’s length and rather stay in the friendzone. Cheating is wrong, regardless and it’s something that should never be done.


15) Have you ever been in love before?

This is an important question because if he hasn’t, then it means that he might have some issues or problems with being in love and being in relationships. 

You probably don’t want to be with someone who has never really been in love before because it means that he doesn’t really know what true love is.

On the flip side, if you find the fact that he’s never been in love before alluring, it’s a great opportunity to show him what love is all about and it might make him change his perception of love.

After all, he’s got you as a guide!

16) What do you like and dislike about dating?

If he says that he likes it, then it means that he’s ready for a relationship and wants to be with someone. 

If he says that he dislikes it, then it means that he’s not really looking for a relationship and doesn’t want to be in one.

His dislike of dating someone could mean that he doesn’t want to be tied down and that he wants his bread buttered on both sides.

Likely, he’s looking for a friend with benefits.

17) Did you have any serious relationships in your past?

You need to ask him this question because if he does, then it might mean that there are some issues or problems that might come up later on in your relationship.

Don’t be afraid to probe and ask what happened, why, and how. This is your chance to get into his psyche and figure out what makes him tick.

It’s not a bad thing, all I’m trying to say is that you need to know if he has a lot of experience with relationships so you can decide if it’s a good idea for you two to get into one together.

18) What do you think is the best part about being in a relationship?

You need to ask him this question because it will tell you how he feels about being in relationships and what he expects out of them. 

If he says that the best part is having someone who cares about him and loves him, then it means that he’s looking for something serious and long-term. 

If he says that the best part is getting to spend time with someone, then it means that he just wants something casual and doesn’t want anything serious or long-term.

Also, if he’s simply looking for someone to cook his dinner and iron his shirts, run. 

19) Why did you break up with your ex?

If you want to know if he’s still in love with his ex, then you need to ask him why he broke up with her. 

If he says that they just weren’t meant to be together and makes excuses, then it means that he’s not over her and doesn’t want anything serious or long-term

If he says that she was just selfish or something like that, then it means that he’s still hung up on her and is probably not ready for a new relationship.

Basically, you’re simply being viewed as a rebound. Something to ease his temporary heartache.

Rebounds seldom work out so if I were you, I’d run screaming for the hills. You’re just going to get heartbroken when he goes back to her.

20) What do you look for in a girl? Do I have those qualities?

You need to ask him this question because if he answers that he’s looking for someone honest, trustworthy, and loyal, then it means that he’s looking for something serious or long-term. 

If he answers that he’s not fussy and just looking for someone who is fun to hang out with and have a good time with, then it means that he’s not looking for anything serious or long-term.

21) What’s the longest relationship you’ve ever been in?

This question will tell you how experienced your crush is and whether or not he knows what a healthy relationship looks like.

If this guy can’t make it more than a few weeks or a month or two, Houston, we have a problem.

Either he’s just very picky, or, he’s doing something that’s making his previous girlfriends drop him like a hot potato.

Either or, it’s a red flag and I wouldn’t suggest you try to become his girlfriend.

22) What’s something you’ve never done before but want to try?

This is a question that will tell you what your crush is like when it comes to his personality. 

If he’s willing to try new things, then he’s probably not as stuck in his ways as some people are.

You don’t want someone who refuses to experiment and just wants everything on the same day every week. 

That kind of person has no variety or spontaneity in his life and will be boring once you get into a serious relationship together. 

You won’t see him that way yet, but this question will give you an idea of what he might be like later on down the road in case anything changes between now and then.

So, if you’re happy to sit at home binge-watching Netflix every weekend, go for it.

If not, save yourself the heartache now and go out there and find someone who enjoys living.

23) What’s your biggest flaw?

While this question isn’t the most important to know, it gives you some insight into what he really thinks of himself. 

If he has no flaws, that’s a sign that he might be arrogant and self-centered, or maybe even a liar. 

His answer will make you feel like he is realistic or totally out of touch with reality. 

No one is perfect. No one. So if he blows his own trumpet and refuses to point out anything remotely negative, sorry, he’s not the one.

Rather stay friends or even better, acquaintances.


These are just a few of the most important questions to ask a guy to figure out what his intentions are.

The idea is to ask open-ended questions that require more than just a one-word answer.

As I said before, you’re not trying to get the guy to talk just for the sake of talking. You’re trying to find out what his motivation is. 

Is he after a relationship or not? 

That’s what these questions will help you figure out.

Good luck!

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