Does a Man Always Ask Out a Woman If He’s Interested In Her?

Does a Man Always Ask Out a Woman If He’s Interested In Her?

Evan, I have a common problem that you’ve responded to lots of times: I fooled myself into thinking that my friend of 10 years had feelings for me, and when I mustered up the nerve to tell him, I was shot down. I thought I had read the signs right. We talked almost every day, he told me I was hot, he told me that he fantasized about me, and we went traveling together. He never actually made a move on me though. Now that I know my feelings are not returned, I’ve cut him out of my life so that I can move on and find someone who truly does love me. I have to admit though, that this whole experience has left me scarred. I was wondering if you could explain how to avoid a situation like this in the future. Do men always ask out a woman they’re immediately interested in? Does love never grow over time? Does the romantic story of “When Harry Met Sally” really just exist in the movies? —Angelina

Angelina, sweetheart. I’ve never answered this question before, and I’m glad you shared your story with me. It definitely hurts to have a long-time unrequited love and I’d be lying to you if I said that I never experienced the exact same thing.

So believe me when I tell you, everything you’re going through is very common — and, not only that, but this will NEVER ever happen to you again. Okay?

First of all, you have to stop beating yourself up over the outcome of your friendship. Any woman in a similar position would have read all of those signs in the same way. I can’t think of many guys who will tell you you’re attractive and claim to fantasize about you, who aren’t at least somewhat interested in something more than friendship.

Usually, when there’s smoke, there’s fire. In this case, there was not.

C’est la vie.

It definitely hurts to have a long-time unrequited love and I’d be lying to you if I said that I never experienced the exact same thing.

But there are some things that you could have been ignoring the entire time you were with him that led to this crisis. The first thing that I can think of is that he’s not some shy beta male who had a crush on you for ten years and was too embarrassed to make a move.

I’m guessing that maybe 25% of guys are that way. Maybe more, but I don’t know too many men like that. Guys who are the way I was in high school — befriending all the pretty girls in hopes of getting close to them, only to discover that you’re in the friend zone.

But for all the other men out there who got the memo in third grade that if you find someone attractive, you ask her out, the easiest thing to do is simply observe them.

If he asks you out, he’s interested. If he doesn’t, he’s not.

I’m guessing, Angelina, that your guy was in the top 75%. Which meant that if he liked you, at some point over 10 years, he would have let you know it.

So, looking back on your history, was your friend somewhat confident, charismatic, and funny? Did he have any other girlfriends? Any random hookups? Did he tell you about other women and ask you for advice on them?

If so, I could have told you from the beginning that he saw you as just a friend.

Men see women as just friends in four fundamental ways:

1. He’s not attracted to you at all — which makes friendship really easy to maintain, without all the sexual tension of the “When Harry Met Sally” friendship.

2. He’s taken and content in his relationship — which makes you off-limits, and even if he is attracted to you, he wouldn’t do anything about it.

3. He’s hooked up with you before — so the mystery and excitement is gone and you can just enjoy each other’s company as friends.

4. He’s a mature adult who’s had enough sex to understand that just because he’s attracted to someone doesn’t mean she’d be a viable girlfriend/life partner, so it’s best not to act on that attraction.

I can only make such a list because there I am friends with women under all four of those pretenses — I’m not attracted to her, I’ve hooked up with her before, I’ve slept around and don’t need to do it again, and I’m married and not ruining a good thing.

So when you’re assessing future friendships with men, first ask yourself whether he’s the shy, awkward guy who may be repressing his true feelings for you.

If he’s not, he’s probably not interested in you and is one of the four men above.

Any questions?

Join our conversation (178 Comments).
Click Here To Leave Your Comment Below.


  1. 121

    There have men that instead of making things easy for me and asking me  out, they tell other people to say things to me and they sneak around and play stupid games and create stress in me that I get to a point where I am thinking about commiting myself into a hospital because of their stupidity. If they could just approch me just say hello and we can move on from there, but NO! they just have to get me to a point where I just want to get commited to a hospital of call the police on them. My god, really!

    1. 121.1

      Always be grateful for the men that never call, never show up, never come along, never enter your space. Be cheerful and be thankful they never came along, to your door, out of the woodwork, across the floor.
      Be happy knowing they were never suppose to come along on your ride, your journey. Sweep any hostility aside and smile knowing they were never meant to. Be secure in knowing this and watch the magic in your life surround you. I know this to be true. I’ve come along way “baby” and I’ve snatched the pebble. I’ve tossed it into the pond knowing that holding onto my vices was ridiculous but letting go started the ripples on the shores of tomorrow. Oh, I’m on a roll today. HA.

  2. 122

    Either they  talk  and approch me in a  appropraite way or   they need to leave me alone. They need to choose!!!! I will call the police on them if they don’t leave me alone. People can talk to me, but when they do thing like what they have been doing I will document and I will call the ploice on whomever.

  3. 123

    75% of men are Alpha males? Seriously?

    Evan, I’m betting you are an attractive women, by most standards. As such, you can’t base this presumption about “men who got the memo in the third grade” on your experiences. How insulting you are.

    I’m guessing that you encounter Alpha males all the time, I don’t doubt. Most reasonably attractive women do. But to abdicate women’s responsibility for asking men out on that basis is irresponsible, in my view.

    While I feel for Angelina, and I know her feelings got hurt, guess what? Her story has happen dozens if not hundreds of times to most men. A man will meet a woman. She will seem interested, even agree to go on a date. Then, usually because she got a better offer, she will cancel; or it will turn out she just really wanted a free meal; or she will stand the man up just to get back at other men; or she will go out with you just to make the guy she really likes jealous; or she will purposefully misunderstand your “date” while she in fact has a boyfriend.

    This is the world of single men. These are the minefields they face. Angelina, that feeling you’re feeling right now? Confusion, rejection, disappointment? That happens so often for men, it’s like air.

    So yes, Erin is right that it’s just the cost of expressing your feelings. And I agree that, if being around him is too painful, then you can no longer be friends. But I disagree with Erin that it’s a good idea to “read the signs.” Why, when it’s so much simpler: if you think you like a guy, ask him out. Know that he might say no, even if he’s attracted to you. In fact, I kind of give this guy props if his reason for not going out was he wanted to keep the friendship or he didn’t think you’d have a good relationship. Of course, if that were true, I take the props back, because why is he telling you those things? Still, you were right to ask him out, and you should do it more often, if you think you might be interested in someone.

  4. 124


    No. Men do not always ask out women to whom their attracted.

    I”m a case in point. In college, I was attracted to someone in every way possible. I never hinted on it. I was just too focused on being a better person through studying, that I didn’t take time to focus on her.

    Had she asked me if I was into her, I would have said yes. Had I asked her, I do not know what she would have said. We were and we are both fit and very attractive.

    So, women, maybe he is into you.

  5. 125

    Evan what you wrote was wonderful! I wasn’t looking for this type of advice, but it sure did help. Men always confuse me. I think they have a shelf life when it comes to asking girls out. Maybe initially he was attracted, but you were unavailable. Then, so much time went on that he thought he didn’t want to ruin the friendship because look what happened 🙁 I am curious to what your friend said to you when you told him. Just being nosey. It’s a shame a friendship got ruined in the midst of this! Keep searching honey, you will find him out there!

  6. 126

    Honestly as a guy I can straight up tell you from well knowing myself and many others that a guy will not ask you out just because hes interested in you, I myself haven’t asked a single one I’ve been interested in WHY? There are a million reasons however I’m sure most would be ignored and chalked up to being a beta so ill just post one reason and that’s rejection. Most guys I have met would not ask out a girl they truly like unless they had a VERY strong reason to believe she would reciprocate those feelings this apply’s to many guys women even the ones women often assume are “ALPHA” not just talking about betas here. You need to keep in mind that as a guy there is well an 80 to 90% chance that we have never even been approached and hit on by an attractive or even unattractive girl and even for those who have had this happen I would bet it was but a fraction of the number of times you’ve had your looks validated by a member of the opposite sex. Point is the saying men are from Mars and women are from Venus makes allot more sense than most realize since we truly live and grow up in COMPLETELY different worlds from each other.

    1. 126.1

      So I am curious; do you ask out girls you really don’t have any interest in? That’s like aiming at a target and missing on purpose. I don’t think a girl likes being “settled for” anymore than a guy does.

  7. 127

    I don’t typically ask a girl out simply because I consider her attractive.

    I look at the whole situation and there are various factors that affect whether I would ask her out. For example, if I work with her, even if I am attracted to her, I wouldn’t ask her out or start any kind of relationship with her. Too much chance for drama.

    Another major thing, is I try to gauge her interest in me. If she is not interested, I don’t bother to ask her out no matter how attracted I am to her. No need for unnecessary awkwardness.

  8. 128

    Failure is the only answer.
    All the top dogs in business say, if you have not failed many times, you will never succeed.
    Don’t repeat the same actions that did not work, that’s insanity.
    But don’t stop the attempt towards the goal.
    Churchill, “Never never never (13) of them, give up”
    There is a guy on youtube who looks for rejection. I think that’s the best way to go about it. That takes out the sting and perfects the game.
    Just like the “Interview” the new resume, the new anything.
    Look for failure, look for rejection.

  9. 129

    I agree wtih what Evan wrote and it’s insightful but for Angela who posted this the biggest thing I’d say is why in the world did you wait 10 years to ask this guy outright if he had feelings for you?

    No matter how you could have known from A, B, or C, or a combination, you could have  known a lot sooner by just asking him outright sooner, much much sooner.

    I mean, how fun could it be to  be friends with a guy hoping or thinking there is more but never getting to that point and  why in the world would anyone put themselves in a long term heart juggling situation like that?

    Friendship is great, but 10 years, really,  putting one’s heart on an  unreiprocated line like that for so long, it’s just something I don’t understand.  

    If I were friends with someone and had feelings, I’d just throw it out there, you are either with me or you aren’t, I value my heart above a friendship, so I’d risk that frienship to save my heart from being  on a fake  string with a man who didn’t love me back.

  10. 130

    Fact of the matter is that some men are using women to practice and sharpen their skills for the main event.   Learn from the lesson because life is too short to allow guys like that to waste your time!   

  11. 131

    If I like a guy and we are talking on the phone and texting and he has not asked me out within a fair amount of time- I start to slowly ‘fade him to black’ as I call it. Which means I slow down on returning his texts or calls. It has worked with some real potentials but it definetly weeds out the rif raf or guys that aren’t worth my time.

  12. 132

    I can say that I wasn’t in a relationship with a guy for ten years.   I can agree there are some warning bells that goes off inside you that tells you that he isn’t right.   I have recently went through a case of a guy who I had been talking with for about two years and I recently decided to be with him in an intimate way.   I was drawn to this guy.   Thinking about it, he said all the right things, but he really didn’t back up what he was saying with actions which I already knew, but for some reason ignored that he wasn’t showing along with telling.   Its nice to tell the lady that she isn’t totally at fault.   Unfortunately it doesn’t stop one from feeling at fault.   For years I held up standards and turned away men after men because they just wasn’t willing to commit or even show any interest in a long term relationship.   I’m not sure why I lowered my standards and values for this one man; but I allowed him in.   I fell hard for him.   Once we had sex, he changed.   He seemed more distant.   I decided to ask “what are your intentions toward me?”   Because I made it really clear from the beginning that I wanted someone who wanted the same thing I wanted which was a relationship.   At 45 years old, I would think that men would know what they want at this point in their life and it doesn’t take forever to figure it out.   His response to my question was “He didn’t know yet”   When those words fell from his lips I knew without a doubt that he had not real intentions of building a relationship.   I knew that his intentions were to string me along as long as he could.   The knowledge hit me like a ton of brick and my heart fell to the bottom of my feet.   He actually wanted to kiss after he said those words to me, but I was so hurt that I just couldn’t stand to look at him or for him to even touch me.   He knew I knew what his plans were for me.   He texted me and in my text to him I told him that I thought it was best if I didn’t see him anymore and I wished him well.   I am so hurt that I just didn’t have the strength to look at him without wanting to cry.   I just could not bear to be in his present any longer, therefore I end it.   It still hurts like hell to know he really never had any good intentions toward me.

    1. 132.1

      His intentions are his.   You broke your own rules.   In anyone’s eyes you broke your rules for him, he may think you’ll break them for anyone.   No trust no relationship.

      So, if you’re certain you want a relationship and you’ve got standards, I’d say stick to them or look wishy washy.   He’s not breaking your heart you did that.


  13. 133


    This is the impression I got from your post. He valued your friendship based on the fact that it was of 10 years duration.   Guys are not always immune to sexual thoughts even with friends.   It could be that he said those things as a way of ‘testing the waters’ to see if you would be receptive to a ‘friends with benefits’ fling.   Otherwise he would have asked you on a date if he wanted to pursue something more serious. You’re response clearly told him that you were emotionally involved and wanted something more.   He possibly “shut you down” because he realized you were not on the ‘same page’.    He was possibly “shutting himself down” too for having those thoughts.    I get the impression that he did value your friendship.   He didn’t take advantage of you.   He probably had a realization about what he did, and didn’t want you to get hurt.

  14. 134

    As a man in what Evan describes as the [bottom] ‘25%’ – those who never tell women we find attractive that we like them – I find the implicit idea that there’s something wrong with me because I keep my feelings to myself to be offensive.   I’ve liked lots of women over the years, but have never said anything to any of them.   I’ve never gotten attention from women – from when I was in high school and college, I have never seen a woman smile at me or had a woman say hi.   With that experience, I’m not about to tell someone who is almost certainly going to laugh in my face – or run away screaming – that I’d like to get to know her better.   The fact is, I’m no worse than anyone else out there – I’m just chronically single and not stupid enough to expect that it change by opening myself to being humiliated.   So enough silliness about grade 3 memos.   C’mon, Evan, in your business, you must realize that the reality is that not every guy is even on the circulation list.

    1. 134.1


      Every man puts himself out there by talking to a woman. About every guy I know has been rejected far more times than accepted. No women I’v dated ever came up to me and said anything. Most women I’ve dated didn’t smile at me first. If you truly believe that you talking to women will always end up with them laughing in your face or running away screaming, then there IS something wrong with you. If you don’t wish to continue to be chronically single, you’ll have to work through it. Never talking to any women out of fear ever will guarantee you stay single.

  15. 135

    Many guys don’t ask women out at all – no matter how attractive they may find them because just flirting with a woman in Western society today could be — and often is — construed as sexual harassment. I’m an extreme introvert, and have never tried to flirt in the first place — I am certain I’d be an abject failure no matter how many times I tried. I’ve had literally no experience with women at all and a lot of advice given is to practice to ‘get better with women’ – whatever that means.   Given  the very real potential for legal issues to arise from trying to show a woman my interest in her just makes me avoid it.   She’s just a human being after all – my life, reputation and hard work are worth more than the potential for another person  to destroy  it just because she isn’t attracted to me.

  16. 136

    No, even if I’m very interested in a woman (and I often am), I will not ask her out because just as   she doesn’t know if I’m [one of a small minority of men who is] a rapist, I don’t know if she [is one if a small minority of women who] will publicly accuse me of sexual harassment just for saying hello.  No, that’s not an exaggeration.   I remember being 18, standing around for a bus, asking a woman who was probably 23 for the time because my phone was dead. She went off on a rant, apparently perceiving this as a pickup line, and judging me of course unworthy, even though I just wanted to figure out when the next bus was. And every time I said “sorry to bother you” she’d go off again. “what kind of man says I’m sorry!!” It’s women like that we remember, when we think about saying hello, and it just shuts us down completely. There are many more stories I can recall right now of that sort. The fact is, I’m now 31 have never so much as held hands or kissed a woman — and of course I’ve never been asked out by a woman either.It’s not ‘rejection’ that scares me – it’s being screamed at and called a creep in public, and / or accused of sexual harassment with all the ensuing destruction to all areas of my life, that completely destroys my wish to put myself out there to get a chance at a date.   I’m not blaming anyone for this – men have done incomparably more unforgivable things to women than women have done to men – but I work very hard and won’t risk my freedom, my career, my reputation – just because one woman – who could be the attractive woman I see – thinks all men are rapists.     

  17. 137

    Most of the time it never works out at all since most women are very picky these days.

    1. 137.1
      No Name To Give

      People are picky. Neither gender has that market cornered.

  18. 138
    Dennis R.

    I refuse to ask out any woman on a date because I figure if she is really that interested, she will ask me out, or at least hand me a note with her name and phone # on it and say: “I really enjoy talking to you and your company, let’s get together some time.” I refuse to ask out women on dates because I feel that is a societal construct. That we all should be asking out each other. But as long as I hear these stories of dads who will not permit their daughters to ask out guys, or women who refuse to ask out men because it is improper or whatever nonsense, I am content to be single and celibate the rest of my life. I do it on principle. I don’t care if society will never change. I stand on principle, I don’t feel it is my responsibility as a man to ask women out. That’s an outdated sexual role that leads to outdated sexual stereotypes that I am uncomfortable with. Most of all, I just don’t feel they are fair. And I do believe in fairness. If you feel I am a retard or immature or unmasculine, I don’t want you in my life anyway. I don’t believe in roles and stereotyping, period. I would rather be my true self that sell out.

    1. 138.1
      Evan Marc Katz

      How’s that workin’ for ya?

      1. 138.1.1
        Dennis R.

        Pretty good so far. I actually got a date a couple of weeks ago. Was at the produce stand at a supermarket. Had a 10 minute conversation with an older woman who said, “maybe we should get together sometime. You’re a really witty and I’d like to get know you more.” I agreed, and I planned a picnic date. Turned out she was leaving the area in 6 months for a new job (hundreds of miles away), so I had no interest in carrying it forward because I only want a LTR and don’t do hook ups. I am not afraid of being out of the gene pool or being single the rest of my life. As long as I did it on my terms. If I constantly pursue women and got rejected again and again, I would be very bitter on my death bed.

        1. Randy R.

          I do not have issues with guys pursuing women if they wish to, but I feel the world works best when women take the lead. They bear the ultimate responsibility of bearing kids. A dear lady friend of mine has a 6 month year son based on a fling she had with some guy. Instead of leading the situation, she got suckered in by all the guys lies and charm. A bad boy deluxe.. Turns out he wasn’t divorced yet, that he had two other kids out of wedlock. She gave into his pleas for sex too soon. Then he just took off to Egypt from L.A., and now it is a big court/legal mess. With the child a victim. Guys can escape the responsibilities of rearing children much easier than women can. Despite being an atheist, she couldn’t even “think” of having an abortion. The ties between that baby in her tummy and her were too strong. You can blame her for her misjudgment, but she is the first one to admit that she wasn’t proactive enough in dating this guy and finding out way more about him. She swears she will never date another guy again unless she takes the initiative. She and I agree that the best move in the world that either gender can do to initiate is for the female to hand over a piece of paper with her name and number on it and say: “I really enjoy your company. I’d like to get to know you more. Give me a call sometime.” The ball is in his court, but she has taken the lead in blatantly telling the man she’s interested. The move, most of all, doesn’t rope out introverted men who I believe are much better LTR partners than alpha males (Never confuse them with shy men – introverts are just slower to trust, have fewer but deeper friendships/relationships with people, and don’t like being in large gatherings of people. Shy people wish they could be involved in a social situation that introverts wish to avoid). The world works better that way. And kids grow up better that way.

  19. 139
    Timothy Braxton

    I have always said that if women handed over a piece of paper to a guy they’ve known for a bit who they fancy, with their phone # and their name on it, that this is the best way possible to create a happy medium in the dating game. Just give the guy the paper and say, “I am really interested in you and would love to get to know you more. Give me a call sometime.” A middle-aged female dating advisor for women supports this approach. You are still putting the ball in the man’s court. He still has to make the move, but in the meToo age, and also in an age where contrary to popular opinion, many of our greatest innovators, smartest minds and best male relationship partners are introverts (never to be mistaken with shy men – see Dr. Jung on the difference between shyness and introvertedness. Also see the book entitled “Quiet”), this tactic by women gives “permission” for the man to proceed. It also involves them more in the process. I just feel Evan that women have too much to lose in the reproductive game in modern times for women to take a back seat, be chased and be non-proactive. I’m not saying allowing men to be passive, but women need to be more involved. I have a good female friend who got pregnant from a guy, and he just bailed to a foreign nation. Men just have the capability of bailing and being irresponsible in the raising and funding of children than women do. Carrying around that baby for 9 months creates an intense bond. Women need to be more proactive in kicking away the so-called alphas who are just not good for raising kids and having a marriage. If your job is more important than your family, you have it wrong. No one goes to bed saying “I should’ve spent one more day at the office.” I am not encouraging guys to be passive, but I think we have room for women to more proactive without them being desperate or going completely against our biological tendencies (although I will say that evolutionary psychology, for better or worse, is not considered legit science in most psychology departments). Look, I have had 2 different women ask me out of on dates, and it didn’t screw up the relationship dynamic. But I sure as heck paid for the second date of the girl I liked. I think there are gray areas between alpha and beta that people find themselves, and they are not asexuals.

  20. 140
    Suzanne R.

    I am in 100% agreement with Timothy Braxton. I don’t agree that 75% of the world contains alpha males, and that 25% contain betas or shy guys. There are in betweeners. I own a business and often go into a local credit union for assistance. Even though I own a business, I wouldn’t call myself an alpha female. I am pretty much a traditional 30 year old girl when it comes to dating. One of the men who works at the credit union is my man. We had a number of conversations over several months. I could tell he was interested in me, and I was seriously interested in him. But like a typical woman i was just too shy to ask him out. Brian is what I call an introverted man, and like Timothy Braxton I recommend that all women and men on this site read the book “The Quiet Rise of Introverts: 8 Practices for Living and Loving in a Noisy World” by Brenda Knowles. It demonstrates that shy men and introverted men are not the same. Brian is very successful. He is just quietly confident. He is also not macho. He likes different things like musicals and collecting stamps and reading psychology books compared to other guys. He later told me that he was not only nervous about asking me out, but he had seen other men at the union ask out women who were business associates and had seen it go badly. One day I just said: “Boy, you are mine.” I handed over my name and smartphone number on it. I told him I found him to be attractive, really smart, attentive and interesting company, and if he ever wanted to get together, give me a call. He called in two days, and behaved in every way that so many women like myself dream about. He turned into my knight in shining armor. He just needed to be thrown a bone. As Timothy implies above, my note gave him permission to pursue me as a woman. This increased his confidence to giant proportions. I really believe this is the man I am going to marry. I have since advised all my girlfriends to do not just totally dismiss guys who you feel are “into you” but won’t ask you out. You never know what’s going on. Also, he’s the first introvert I have ever dated, and I am never felt this emotionally close to a man before, yet felt so secure and protected. I get both things as a girl that I need. Introverted men are totally misunderstand by our society. Believe me, when I handed over that note was handed over, Brian became a different man. Still different from the raging, Donald trump type alphas, but definitely a guy who pursued me. We actually joke about this because he hates it being referred to as “pursuing me.” He just says, all I wanted was to be with you more and more. I never played hard to get or any of that bullcrap.

Leave a Reply

Your email address will not be published. Required fields are marked *