Should You Ever Tell A Man You Like Him Or Ask If He Likes You?

in Understanding Men, Women
Man Woman Talking Tell Him She Likes

Written by Peter White – Creator of Why Do Guys…?

There’s a “sort of” rule in dating – “Never Tell A Man You Like Him.” 

Except in the real world of dating, rules are sometimes meant to be broken or they are at least designed to be slightly altered to fit the situation or need.

This led me to question “revealing your feelings” and how the rule applies to everyday dating:

  • Is there a right time to tell a guy you like him?
  • How you can benefit from not just blatantly telling a guy you like him.
  • How following this rule this rule can lead you to men who are less approval seeking or needy.
  • Will telling him make you less or more attractive (in his eyes)?
  • Why would you feel the need to tell him and what does that say about you?
  • If you’re not allowed to “tell” how DO you let a man know you like him?

I’ll briefly cover everything and if you still have any questions leave them below…let’s get started because once again, I’m eager to tell.

Is there a right time to tell a guy you like him? Or should you tell him at all?

FACT: Men are terrible at determining if a woman likes him. (generally speaking of course) Lots of them just don’t get it and they fail to notice the subtleties you might believe are not subtle at all. Meaning it might be clear to you and everyone else that you like him but not to him.

This often leads to women more than willing to tell a guy, just in case he’s not getting it. This also often leads to a bigger more debatable question about upfront and honesty in dating but I’m not sure if we’re going to get into that today.

Let’s say – If you’ve dated him for a while and his actions prove without a doubt he likes you, but he appears to question you liking him back, you might wonder if telling him is okay and that’s a very good question.

SHOULD you tell him even under those circumstances?

That depends on what type of guy you’re looking for and how far you’re willing to take it.

Higher “quality” men or the ones with the most attractive personalities or lives do not ever need to be told. They assume it or they just don’t care. Sure they are rare but they ARE out there.

They WILL know. They do understand and can absolutely tell when a woman like them. Unfortunately some of them might even be a little too cocky about it as in my case.

The guy who doesn’t figure it out may be less secure about himself.

He may not feel good enough or have a large enough self-esteem to believe it’s possible. He may be more likely to become needy, desperate, clingy, jealous, or revert to constantly fishing you for information. He might even cause a preemptive breakup because in his mind, he feels unlovable.

***THE EXCEPTION: When you’re in an exclusive relationship as an act of romance. After all isn’t that what romance is about… A prelude to intimacy in which we show through our actions how much we care for an individual. Hopefully if you’re already in a relationship the guy doesn’t need to be told but it’s good and smart to let him know in a way which builds the attraction in love. IF this is the situation you’re in, I want you to read about triggering his HERO instinct because it really does work. Here are the articles to prove it:

He does need to be told constantly or if you feel you have to confirm your love continually or he gets all bent and pissed off about it all too often, then you have a much more serious problem on your hands. Sorry that won’t be covered today so I’ll introduce you to Katie & Guy Hendricks. They are relationship experts and have posted a few article here at the approach.

Back to the issue…

Think about what type of guy you really want.

If you stick to the rule…“Never Tell A Man You Like Him”, will it lead you to a man who is not too approval seeking or needy?

Yes…Sticking to this rule  can absolutely lead you to a better more secure man. You might have to go through more men or go out on more dates but I feel it’s worth it.

Dating a lot and often WILL lead you to a better man if you do things just moderately right. Not dating often and sparingly while doing everything wrong won’t help at all. Doing things 100% right with every guy (which is probably impossible) but limiting the amount of dates with different guys you go on, will also more often than not – not lead anywhere good.

Date more often… always!

Here are two quite different articles to prove my point.

“Only again proving to me, dating multiple guys or exploring our options or securing our present FIRST proves to establish better more happier marriages.”

Why Dating Multiple Guys At The Same Time Can Lead To Better Marriages


“Once we meet a man we really like, we women tend to dive right in. We want to give our hearts, mind and very soul to a man, and meld together into a perfect relationship. We give away our exclusivity before a man gives us the commitment we want.

When we close off our options with other men too soon, we actually sabotage our ability to get the commitment and intimacy we so desire.

It’s the biggest mistake women make, and you need to stop it – right now! – and start dating many men at the same time until you have the commitment you want from the man who is right for you.”

Why You Need To Date Many To Find Your One

This is a hard truth which can not be denied –  and I suppose it’s equally as hard for men because I’m asking you to let go of so many men who just don’t get it.

BUT Consider all this “letting him go” or “avoiding a guy like that” seriously before you cave in and tell him:

If he does not show signs of understanding women on any level where he believes in himself he will not suddenly get it three years down the relationship. He will only be reacting to what he understands is how you act.

Remember your part in relationships, how they grow, and what you should be learning about developing a happier more secure relationship…

You’re not learning how to train men,  You’re learning how to better share your life with someone else… period!

Let’s go to the other end.

What if you decide or think you’ll just ask him if you likes you, to avoid this problem…  Will it make you less attractive?

Attractive Woman Man Deciding What Say

If you ask him, yes it probably will for most guys. Not any less physically attractive but he may lose interest quickly. Which is the harder part of dating and getting guys – gaining and keeping their interest to something more than just physical and longer lasting.

Unless you feel without a doubt he’s a great sincere man who just does not seem to get women but you want him anyways.

Which is why this rule is so confusing. Easy to understand but hard to determine when to implement it and when to ignore it and just go with your intuition or gut feeling.

Truthfully I’ve known a couple of women who like to be the leader and they don’t mind being it. They actually prefer it. Hey, it’s okay to be the leader of your life but when it comes to relationships, handing over the leadership role early on usually does not end well because of what it does to the guy AND the type of guy you end up with who is willing to give up so easily.

If you want a relationship with this type of man you may have to become the leader in the relationship and take charge. I don’t recommend it but I would hate to see so many guys miss out on you just because they were not given the education I have, or even know where to begin.

Just PLEASE consider an alternative first and seriously think about what you’re doing first.

Let me ask you this next question which is directly related…

Why do you feel the need to seek the approval of a man?

Remember school. How we HAD to tell a boy or girl we liked them. How “Johnny” passes a note to “Sarah” to tell “Lisa” he likes her…? Remember that stupid little paper or petal game so many girls played growing up…?

“He loves me. He loves me not. He loves me. He loves me not.”

If you find yourself asking others or even yourself if you should tell a man he likes you it pains me to say…

You are exhibiting a classic sign of neediness and you are seeking approval from a source outside yourself.

You’re living out a childhood game which was fine when we didn’t understand our emotions and how to deal with them, or how dating works, but as an adult only proves itself to delay success in meeting the “man of your dreams.

Approve of yourself and others, including men, will follow your lead. I could quote a hundred plus different articles to prove this to you but for now, I’ll pick the first one I find:

“Have yourself to rely on. Neediness in an emotional and material sense is one of the biggest roadblocks to greater attractiveness. Sure, guys may get the occasional kick out of being your knight in shining armor, but for the most part you’ll need to let them know you can live without their brute strength.”

How To Be The Girl That Guys Want To Date

If you’re not allowed to “tell” then how DO you let a man know you like him?

You flirt with him.

You tease him.

You playfully interact with sexual overtones and in a strange twist you actually accuse him of liking you!

You challenge him.

You lure him.

You LET him chase you.

You make sure you have a great life a guy would want to be a part of because you’re worth it!

Here’s a very simple example related to this article on telling:

NOT GOOD: “You’re awesome. I really like you.”

BETTER: “Wow you smell great tonight. You must really want to impress me.”

Since flirting is an adult or mature way of showing you’re smart, confident, and have a sexiness about you which is desirable it’s important to learn how to flirt better to attract more men.

Don’t tell a guy you like him. Don’t ask a guy if he likes you. AND… you will naturally appear less needy and start to display more traits which will trigger his deeper attraction and interest in you.

Flirt with him and tease him the right way and you ARE showing you’re at least interested – and if he takes the hint – or runs with the game – or responds by calling you out on each level this undoubtedly means…

He likes you.

Assume it.

And assume since you’re appealing to his “manly” urge to be with you – he’s going to love it because it’s a REAL challenge to him.

A major benefit of becoming a great flirt and someone fun to be around is to never have to worry about whether you should tell him you like him.

If you’re still not sure why you feel the need to ask this question or tell a guy, consider this type of behavior is constantly reinforced in those who find themselves in one bad relationship after another.

With each failure your esteem may drop causing even more questions like this to appear. You start second-guessing yourself and your attractiveness to men because you’re doing what you can to avoid another failure.

“Should I tell him?” or “Does he like me?” are just two forms of second guessing yourself.

Evan, in his quest to help women find better men profoundly states this…

Men win you over by giving to you.

We ask you out. We call you. We pay for dates. We initiate sex. We ask for commitment. We propose marriage.

We give. You receive.

Reverse this order by asking him out, initiating sex, asking for commitment, or proposing marriage, and a masculine guy will feel, well, emasculated.

Thus, if you want a masculine guy, your greatest move is to embrace your passive feminine side.

Untangling your past experiences and opening yourself up to new and more exciting experiences today, can and will stop many of these questions from ever coming up. And wouldn’t it be great not to have to question your every move in a relationship or in dating..?

The Secret to Keeping a Man: Forget the Future, Enjoy the Present

Exploring this seemingly innocent question or dating rule, ” Should You Tell A Guy You Like Him?” has definitely shown it’s more than just a simple thing:

  • It shows the absolute truth in attracting better men, and how by not just telling a guy you can weed out the lower esteemed guy who will not work well in a relationship.
  • It gives you a clear “scale” to mark your esteem and your level of ability to flirt. Meaning there are more clever less intuitive ways to show a man you like him which are by far more powerful and effective gaining his complete interest in you.
  • It unlocks how your past failures can almost invisibly affect your present which in turn affects your future relationships.The need to tell comes from somewhere and that must be untangled or figured out IF you want to solve this problems and gain the confidence to never NEED to ask a guy if he likes you or tell him that you like him.
  • And this is just what we can cover today!

As always these so-called “rules” of dating and attraction are there for a reason – follow them correctly and you can start attracting better or more ‘masculine’ men in your life. 

I personally don’t like dating rules but some of them are important for some men women to follow to skillfully get past all the nonsense and troubles dating often presents to us.

Hope you enjoyed this episode of the secret dirty truth about men. Don’t miss the next one by signing up below. Who knows what will be covered next. This one didn’t reveal too many secrets about men but if you read between the lines, hopefully you’ll have a much clearer of man, how we work, the types we are, and best of all HOW to attract the better right guy for you.

Thanks for stopping by. All the best…

Your guy friend, Pete

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30 comments… add one
  • Claire

    Hiya Pete.

    There is a man I talk to quite often when I see him out and about. Sometimes we can talk for a while, sometimes its just a passing hello.
    I do get the impression that he is interested.
    When there are a few of us, it always ends up where me and him end up talking amongst ourselves, rather than joining the group.
    He has said he was going to get coffee one day, and I am unsure if that was a subtle hint for me to invife myself ha. I analyzed it too much and obviously didnt go! He lingers when we are about to go our seperate ways.

    There are quite a few signs that he is interested, but I havent been able to actually come up with any questions to find out if he is actually single or not! Because I know my reasons for asking arent just for general conversation purposes…I find myself really struggling.

    I just dont know if im flirting enough to make myself look as interested as i am (I am no good at flirting), or if I am picking up his signals all wrong!

    How can I make this more clear cut without directly putting it out there?

    Thank you 🙂

    • Peter White

      Hiya Claire,

      I’d say it (the coffee) was his way of trying to get you to go with him. Next time a guy does this just say something like, “Oooo afternoon coffee date with some secret hottie or are you just using coffee to steal their free wifi?” Something like that tells a guy you think he’s worth dating and you throw in a little humor too. That should get you a pretty decent idea of what he’s up to AND if he’s single. If you want to invite yourself along just tell me how much you love coffee. How you’re addicted to it and how he’s a bad influence on you. Guys loves to pretend they’re a bad influence on a woman.

      Now… women are very good at telling when a guy is interested so go with your instinct… if it feels right, then it probably is. The lingering and getting you alone to talk are very clear signals a man is interested.

      The flirting thing, it’s not how much you flirt, it’s HOW you flirt. And how you flirt can get a guy to reveal a ton of information you can use. It also lures him in. Something you should do… lure and then lead him in the right direction. You should NOT have to do more than that. It sucks this guy isn’t taking the hints you’re giving him but some guys are like that – they want a guarantee with a woman to avoid rejection instead of just going for it – which works better even if she’s apt to say no.

      I say keep doing what you’re doing Claire. Add to the conversations things you love to do which he might offer to do with you or take you there.

      As far as finding out if he’s single, I’d use the old “girlfriend” technique I often use on women. Bust his ass on being a pain in the ass boyfriend. Make sure he’s laughing and it’s funny. If that fails make him believe you think he’s a player or how he must have so many women chasing him. Women use those “lines” on me all the time. It doesn’t work on me but on most guys, it works.

      If nothing is working, talk about yourself and your single life then he’d be more likely to add to the conversation with his own details.

      There are many conversational flirting techniques you can use without being direct but in the end, you don’t have to know. IF he manages to follow through with all the flirting, you’ll find out sooner than later where he stands.

      Your guy friend,


  • Shelley

    This is very complicated! I was and still am very good friends with this guy. We were very close in high school. Sort of dated but not seriously. After we graduated from high school together, her went off to the Military but before he left I told him I was scared for him to go and that if he’d stay I would marry him. Probably my biggest mistake ever in losing him. I never saw him or heard from him again until our 20th high school reunion. In the high school reunion address book were a few questions and one question asked “if you could go back to high school for one day what would you do.” He said he would tell me how he really felt about me. We were both married at the time. 20 years went by and a friend from ou high school graduating class put together a page on Facebook where we could all reconnect because our 40th reunion was not to far from then. So, I reconnected with him. We talked some back and forth. He was in the middle of a divorce and I was still married. He was not able to attend the 40th class reunion. Since then, I have divorced and I can not quit thinking of him. He was in my city about a year ago for one of his kids wedding so I told him if he had time to contact me and we could grab a coffee and catch up. He never said OK or no but I did not hear from him. The reason I think he might be interested in me is because last fall after my divorce, I changed my name back to my maiden name plus I had new address and phone number. I accidentally sent all my new information to him instead of my step sister in law. I was so embarrassed that I immediately sent a message to him explaining what I had done. He thought it was funny and said he kind of liked knowing where I lived. So I’ve not heard anything from him since. So I am not sure what to do now? Do I just leave it alone or do I try flirting with him to find out if he is interested? He lives a long way from me and I am thinking that he would not leave his home to be with me but however I would leave mine to be with him if he waned me to. I have always liked this guy and hate that I never made it clear to him!

    • Peter White


      Flirt with him. Do what you have to because just maybe something will come about. It’s been too long to wait around for “something” to happen. Make it happen yourself. He’s probably going to have trouble with the distance but if it’s all cool, I’m sure both of you can find a past it.

      Either way – enjoy the interactions no matter how long or short they are and have fun with it. If you’re reaching out to him, chances are he’s going to get the picture that you’re interested in him. How? or Why? Well let’s leave that in up in the air for now.

      Again – flirt – Have fun – Enjoy it – Let him enjoy you.


  • Unknown

    Hi Peter,
    I’ve been seeing him about a month now. We dated 3-4times a week. He told me he only sees me and wanted to make a plan to hang out with his friends. He remembers what I like and what I don’t like. He now seperated and getting divorce and I am also getting divorce soon. It may be short amount of time that we dated but he showed interest to me and I wanted to see if we can be exclusive later on. Rather than asking him directly I asked him how would he feel if I see another dudes but I don’t want to see other man, just asking. What I expected was him saying he wouldn’t like it. But instead of that he told me he can’t tell me what to do. He would be jealous but also told me to shower and see him after I sex with other man. Next time I see him I’m thinking about tell him why I asked him that way because I didn’t want to scare him off, be honest with him. But not going to ask for the answer to be exclusive. Tell him how I feel and I wouldn’t be happy if he wants to see other woman. Do you think this will work? He seems pretty honest person. He said don’t ask me a question when you don’t wanna hear the truth.

    • Peter White

      You wrote, “Rather than asking him directly”

      Men are not always the best at reading a women one way or another but they’re good at detecting ulterior motives. There’s a great chance he saw through what you were doing. He knew why you were asking him that and/or he also assumed you feel like you’re already in a relationship with him and was looking for confirmation from him.

      As the worst possible outcome – he also felt that you were trying to find out how many women he was seeing without actually asking him.

      Since this moment has already passed, going back and trying to explain yourself won’t do much good. He’s already imagined what it meant and will probably stick with his first guess or guesses.

      This is also not the time to ask to be exclusive. You must let a man step up when he’s ready to seal the deal. Considering he’s coming out of a separation, whether he commits or not to you, he won’t be in it fully because he needs freedom and time to get over what just happened.

      Sure, go ahead and reveal to him the reason why you were not as direct as you wanted to be. Make sure you start with THAT and don’t just say how you feel. Be honest about not being direct with him.


  • CC

    Are you still giving out advice? If so, could you help me out a bit as I am in a weird situation?

  • nicole

    i been flirting back and forth we have slept together few times.. he flirts back with me on a daily.. it has been a while since we last slept together he apologized foe being distant explined he been working alot and his school. so i asked hhim is he interested in having sex with me still.. because we flirt all the time aexual flirting.. he seems interested then seems NOT to be interestd. i was so confused and in aoo many wlrkmds i did express i do lime him aling witha list of his great attributes and hjs genuine peraonality. and now no reaction from him since i asked him he has not responded to me with anything since i asked. did i blow my chances did i push him away by asking him if he is really interested is having sex as in the beginning we both told each other we were nit looking for anythibg serious sobi have kept it strictly ablut casual sex. now i feel i pushed him away and i dont know why he doesnt respond ..

    smitten and confused

  • Kim

    Hi Peter,
    I just read your article now and very helpful. However I really need your advice on my situation as I met this guy from online dating a month ago. He’s divorced and has a son which I am totally fine with. We dated twice however the 3rd one got cancelled as he had something on which he apologized for and said will make it up to me. On the day that we were supposed to meet I made a joke about it which I think was a wrong move I said I am willing to drive where he is if he’s worried about the time and he replied back as well as said that he’s not fussed about driving where I am from, it’s just that his son was with him on that day. I did not think of apologizing for the joke eventhough I know it came across as being pushy eventhough he apologized already for not being able to make it. I wanted to take back what I said but I can’t. And since then I feel like if I don’t message him he won’t message me first although he does reply to my messages. I really like him and I don’t know what to do… please help
    Thank you

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