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 (163 Comments).
Click Here To Leave Your Comment Below.


  1. 31

    I had this happen to me a few months ago, ut luckily it only went for a week of intense emotions between me & the guy (full-on flirting, full-on sexting, and he specifically expressed his interest in me). Yet, he never asked me out while I already started to fall for him. Thank goodness my bestfriend warned me on this. Her words of wisdom that i would never forget is:

    “Men’s words are all trash talk. Never believe them unless he actions them.” In other words, in Evan’s language it would be “Men who really want you will ask you out. Otherwise he’s just not that into you.”

  2. 32

    @ Heather #27:

    Dating that guy wasn’t a disaster because it was a “friendlationship”, it was a disaster because he was an asshole.

  3. 33

    Way too much over analysis here. Whether the split is 25-75 or whatever, isn’t important. Whether the guy is flirting with you is not so important.
    What is important is what is going on between BOTH parties. It takes two to tango. So he is flirting. What are you doing in response? It is heard to tell in the postings here, because there is not enough detail. It sounds like there is more analysis of the guy’s flirting than just getting in there and interacting with him to find out.
    It sounds like there is some interacting, because of comments like “we talked about it” and so on. But if you are not getting clear answers, then the interaction is not effective.
    Here is what is effective: tell him about your feelings. If he is a keeper and he is interested, he will respect that. If he is not interested but is just a good man, he will tell you where he is coming from. If he continues to be ambiguous, then he is exactly the type of guy you need to DUMP as EMK says. You wouldn’t want someone like that in your life even as a “friend.”

  4. 34

    A few of the women here have seriously skewed views of “shy” men. Insecurity can appear in anyone, regardless of how outgoing, charismatic, etc. they are. Furthermore, the way Flower White writes, you’d think all these guys are helpless and need to be handheld through the entire process. As someone who hovers in the middle of the introvert/extrovert scale, I’ve experienced both sides of the story. I have been the guy who makes the bold move, and I’ve been the guy who isn’t sure, and has waited a fairly long time to assess things. But I’m talking weeks or months; sure as hell not ten years.
    Frankly, the whole shy narrative in terms of the OP’s letter seems like a red herring. Giving those kind of compliments and talking about fantasies with someone doesn’t strike me as the kind of thing a lot of shy folks do. I don’t really know what his deal was, but I do think the OP made the right decision to step away and move on.

  5. 35

    Woman should ask a guy out if she likes him. Rejection is a part of dating. Guys have had to face this problem for eternity. Woman want equality then suck it up and do it. Or give a guy a real hint at least, like suggest off-hand you do something together.  If a guy is interested he will take that as a sign to ask you out. If that fails then he doesnt like you.

  6. 36

    Exactly Andy, so it’s bad advice to women for a woman to ask a guy out–taking on a man’s job, being in their masculine energy, which ultimately is not attractive to a man.  It’s the man’s job to pursue (and yes, face more rejection, that’s life) and a woman’s job to be receptive to that pursuit.   Look at it this way, it’s rejection to a woman when a man doesn’t call her or drops off the face of the earth.
    Men and women are EQUAL, but DIFFERENT.  Nothing will ever change that.    

  7. 37

    Daisy, in your post you mentioned the phrase “men’s words are all trash talk”. This seems to suggest that men are not being honorable when they say certain things. I do think this is an unfair generalization. Oftentimes men (and women for that matter) are put in a position where they can’t tell the truth, or where they feel they have the responsibility to say certain things. Cases in point :
    1) when he wants to be “nice” in a situation that is awkward or not especially pleasant for either party – ie he wants to break up because he really can’t stand you but of course he can’t tell you that to your face. 
    2) when he feels a responsibility to help you or to make you feel better about yourself – ie you are seriously depressed and think you can’t attract boyfriends because you think you are “ugly” and he says no, no you are not, you are beautiful (which you may or may not be in his eyes).
    Sometimes he makes a mistake and says certain things which, on reflection or hindsight (or maybe when he is sober) he realises he shouldn’t have said. But then it is too late and he does not want to appear stupid or to revisit the issue by correcting himself to you – eg. you are both married and he drunkenly confesses an attraction to you.
    This is not to say that there are many many occasions where men deliberately and knowingly tell untruths for nefarious or less than honorable purposes. Anyway, you get the picture………

  8. 38

    Always a good reminder.  This is why I don’t like initiate contact with guys online.  If they were interested after looking at my profile, they would have contacted me.  

  9. 39

    @ Joe:
    Well yes, the guy I ended up dating was a total asshole, it just took me awhile to figure that out.  I really should have listened to the warning signs.  My problem in the past with dating, was fearing that my divorce would leave me jaded and bitter and that I should give men a chance.  Now I know better.  Good point there.
    @ Andy #36
    You obviously haven’t read Paige Parker’s “Dating Without Drama” blog.  In there, Ms. Parker talks about just that, how we women are taught these days to chase after men, and then we find out in the end that….wait for it….most of you guys are actually turned off by that.  If a guy can’t be bothered to ask me out or get my number again, well then I guess we’re not going to go out.  Just ask my boyfriend, when we first started talking online, he offered his number and in return I sent him mine, and I told him that I didn’t call men, and that if a man wanted to see me, then he needed to ask me out.  20 minutes later, he called, and we have been together ever since.  There’s no way I’d ever ask a man out if I am ever single again.  Yikes, that’s just a recipe for disaster.

  10. 40

    I can completely relate to Angelina, I’ve been there before. I think another way to think of it is this, if you didn’t have any feelings for the guy, how would you interpret his actions? For example, some of my guy friends compliment my looks and I don’t give it a second thought because I have no romantic feelings towards them (and it also seems completely platonic from their side). However, take the same guy, same words etc, and add in feelings on my part, and you’ve got a whole different cocktail. As women we like to read into things and our perception (like men’s) is very dependent on our position on something. See what I mean? If the guy had an inkling that she was interested and still said thi stuff, I think it wasn’t very considerate, however he may have just thought she was an awesome female friend who e could be that open with. What I learned from my experience is to b really aware of yourself and your emotions, the primary person for looking out for yourself and trusting, is you. 

    @Ileana, I like your approach a lot. If I had paid closer attention I would have noticed these clues. But yet I still felt the need to oice it (as EMK put it in one place I read, you can lay it out if you’re not gaining from the situation and he doesn’t follow, you made the right move in cutting him off. For 22 you’re lucky to be ahead of most at that point! And I agree (from an earlier post of yours) men in Europe do seem to have a very different approach when it comes to pursuing women. 

  11. 41

    To DAN #34
    Why I have to tell him about my feelings? If he is a smart man, he will realize the fact I’m in love with him after my actions.
    To nathan #35
    I agree that the insecurity can appear in both women and men. Of course there are shy men, just because you men also are human beings. You meet some beautiful and nice woman and sometimes you feel this insecurity and shyness.
    To Andy #36:
    No, women shouldn’t ask men out. It is still the men’s job to pursue and ask out. The women only have to encourage the man they like, it’s that simple.

  12. 42

    @ Heather #40 & Tina #42
    Its funny how women take one rejection so deeply to heart, yet expect men to deal with the constant rejection when asking woman out. And women wonder why men dismiss them so easily?? 

    So a woman feels special because of the flirting, flattery, and etc she gets from a guy, but men just do those things as part of the “chase”. Men have been conditioned to take emotions out of the “chase” so rejection stops hurting. But this means a guy can chase a woman on minute, then dimiss her a second later without much after thought. Woman get angry about this but its what men are expected to do right?? 

     If woman want things to change, they will have to accept doing things differently like taking a risk and asking a guy out.

  13. 43

    @ Andy 43,
    Oh, Andy.  I’m sorry that you’re so angry about this.  But truth is truth.  I have tons of male friends who complain about women coming onto them, chasing them, etc. etc.  The truth is that you men are WIRED to chase.  It’s biology, plain and simple.
    If it bothers you that much, then I’d suggest that you date women who do want to chase you.  But please don’t come back here and complain that “you women are all psycho.”  Talk about a double standard.
    There is no way, at all, period, that I would ever, ever ask a man out.  Period.  And trust me, I used to be a girl who would chase guys.  My dating life got a WHOLE lot better, and less dramatic, when I stopped that behavior.

  14. 44

    Heather @ 44, I totall agree with you.  Its been my experience as well that men just really do love to be the ones pursuing in the initial stages of a budding relationship.  Of course they want positive signals, that’s just common sense, but they are rarely open to or enthusiastic about dating a woman who chases them, and that’s just the biology of it, plain and simple.  I’ve never asked a man out, and I never will.  And I’ve had no problem over the years in getting plenty of guys to chase me.  I like being chased, they like the thrill of the chase and all is good.  🙂

  15. 45

    Heather and BC, you are both 100% right.  #37 talks more about masculinity and femininity–important concepts that aren’t going to change.  We just can’t mess with biology like that. 

    Heather, you sound like me!  When a man asks for me to call him, I say “I don’t call boys, but here’s my number.”  They totally get it, and I think like being ‘challenged’ like makes them step up, and makes them feel more masculine.  And when a man feels masculine, he has more passion for himself, for the woman and for life. 

  16. 46

    So ladies, to chase or not to chase–that is the question:

    If you’re on, are you just sitting there passively, waiting for guys to click on your profile and hopefully be interested enough to message you?  Or do you go ahead and wink and/or message guys?  If you’ve done both, has there been any difference in your success rate…I guess you could quantify by how many dates have come from one method vs. the other?

  17. 47

    @Heather #44

    No anger on my part, Im just being realistic. The point is that when a woman chases a man they emotionally invest too much and to soon. Men dont do this and it makes life easier. Be a man or woman, the idea is to never “chase” because if the other person is really interested you wont have to chase.

     I just think that women need to take a page from the mens playbook and take rejection with a grain of salt  and move on. Woman toil and beat themselves up too much wondering if a guy is interested in them. And you know what guys know this and prey on it. The easiest thing to do is just to be direct and get it over with. 

    Most of what EMK writes about is changing and controlling what you can, which is yourself.

  18. 48

    @ BC and Michelle,
    Exactly!  My boyfriend said that when he saw my email that I wouldn’t call guys but gave him my number, he realized that if he really wanted to meet me, well then he’d better step up to the plate.  And he did.   I’ve had guys get very turned off by my chasing them, initiating dates, etc, in the past.  About a year and a half ago, my really good girlfriend had me start reading Paige Parker’s “Dating Without Drama” blog and she talks alot about that, about how we need to stop chasing down men, because we cause ourselves too much drama and pain when we do that.
    Absolutely, we should show positive signs of mutual interest and be encouraging, but the next time I decide to “man up” and ask a guy out, will be a quarter past….never. 🙂

  19. 49

    I find it a little shocking how most women sort of imply asking the man out is beneath them, or they are too good for it is some way.  Maybe you will get all the dates you need, but if you are not exploring all possibilities, and we can surmise being on here, your love life isn’t exactly where you want it to be, you really have no room to complain.

    1. 49.1
      Evan Marc Katz

      Asking out a man isn’t “beneath” women; it’s just largely an ineffective strategy, since most confident, desirable men will do the asking out if they’re interested.

  20. 50

    I asked men out in the past. Not much happened beyond one date, if that.
    The two men who became my boyfriend? They asked me out.
    The man who became my boyfriend and then my husband? He asked me out.
    That’s enough proof for me about what works.

  21. 51

    @Joe #47

    I have initiated contact with men online (emailing) and have gotten dates out of that approach (i.e. the man subsequently asked me out).  But the few times I have done this it has never lead to a relationship.  In my experience, it sets up a weird dynamic.  I think the men figured hey, what the heck, she’s obviously interested in me, this one will be easy, and they had nothing to lose.  They never followed up, or made any further efforts — either they weren’t interested or they were waiting for me to continue initiating things.  I was always left wondering if they went out with me because they were truly interested, or just hoping to get laid.

    I no longer initiate contact.  I will view someone’s profile so I show up in their lists, but nothing beyond that.  If they are interested, they will contact me, otherwise they are not.

  22. 52

    @ EMK

    Maybe it’s not the strategy but the strategists….but I digress.  If you look at several of the answers giving, you will see more of an entitlement mentality than a master-general plotting. 

    One of the challanges it looks like you have is a bit of latent arrogance that women show – they seem to want what THEY want at all times and think dating should work around that.  To your credit, I think you call them out on that a good deal of the time.

  23. 53

    I think Andy put it quite well in #43, and was subsequently attacked for it.  Great example.

  24. 54

    In my next life I’d like to BE a man so I can do the chasing and asking out – sure beats all the hanging around wondering if the phone’s going to ring…. But in THIS life, where I’m a woman, I do wait for men to do the asking – not because I’m scared of rejection, not because i don’t want to just go ahead and ask men out but because i am convinced it is ineffective, as Evan says. This approach also applies to other area, particularly sex – all that proactive “tell him what you like in bed, he’ll be delighted” stuff is just nonsense. Men don’t want to hear what you’d like them to do in bed, they want to hear that you like what they ALREADY do in bed.

  25. 55

    @Joe 47, I don’t ask guys out in real life.  But online I do contact men.  I don’t ask them out though.  I think online it’s harder to encourage a than it would be in real life.  I have gotten fairly similar results whether I contacted them or they contacted me.  But I’m not chasing or asking out.  A simple “hey what’s up” type of message that would be akin to smiling and saying hi to someone in real life.  But I do agree with Jules, that the men who do contact me, actually write me emails with effort tend to also put more effort into dates.  They are the ones that seem to be really excited that they get to meet me.

  26. 56

    @ Helene – you are WAAAYYYY off the mark.  Sure, men like positive feedback on their performance, but it’s not they don’t want to be adventerous, it’s just they generally don’t want to hear something “let’s try this thing my ex and I used to do”

    First off, do you women think men asking you out is highly effective from a success rate standpoint for most men??  I see women citing a couple failed attempts and throwing the baby out with the bath water.  Most men that aren’t shy get shot down DOZENS of times.  And let’s not forget as a man, we are FAR more likely to run into women who will be extremely unkind in rejection or do it for some sort of ego boost at your expense than women ever are likely to encounter from men. 

    Also, like Andy pointed out in another post, if you are coming on way too strong, and talking about getting married or meeting his parents the first 5 minutes, of course that’s not going to work.  I think it’s more to do with women not developed their approachign skills vs. this biological urge you all keep citing.  I’m sorry ladies, but your excuses sound weak.

  27. 57

    Let’s get a couple of things straight.  I do not think asking men out is “beneath me”.  Obviously you didn’t read what I wrote, in which I stated that a dating blog, and EMK has even backed this up, that asking men out has proven ineffective.  That is not an entitlement attitude.
    Second of all, I do not expect men to work around me in dating.  For you to assume that is just out of line, plain and simple.
    I’m very sad to see so much anger coming from you in your postings.  I would wager that the vast majority of the women posters on here are not the arrogant beings that you make us out to be.  If we’ve chosen not to chase after men, well so be it.  As I suggested to Andy earlier, maybe you might want to go somewhere where women will be interested in chasing you.
    As a matter of fact, judging by your postings, there seems to be an entitlement attitude on your part, “Well why should I have to do all the work, she better man up and do the work or else.”
    I stand by what I said earlier.  Men are wired to chase, it’s in your genetic makeup to do so.  We women are wired to BE chased.  There’s nothing wrong with that and no judgment in that, well until you started accusing some of us for “attacking” others for stating what we feel…..

  28. 58

    @ Heather

    Please allow ME to get a few things straight for you:

    1) I did not call you out by name.  I’m not sure if you have a Guilty conscious or my comments hit a nerve, but you are WAY overpersonalizing them, especially the part of men dating around you.  Actually, you misunderstood that point.  I’m saying that women are often not flexible and willing to try new things.  It would be like saying you were starting a diet, but you still are going to eat all the cookies and ice cream you want.  You would think dieting should work around your refusal to give up that junk food.

    2) You ignored my whole point about “effectiveness”.  Maybe it’s not an ineffective strategy, but just that you (and other women who have the same complaint) are not good at it yet, from lack of practice/correction

    3) Sorry, but the ad hominem attack to say I and Andy are angry simply b/c we don’t agree with you is flimsy.  I don’t think I said I want women chasing me or anything threatening like “or else!”.  Please don’t project things I didn’t say.  And please re-read you quote about entitlement mentality – how the heck is it feeling entitled if you are talking about taking a step toward equality?!

    4) This “wired to chase business” is funny.  Not saying I fully disagree, but I have a sneaking suspicion if your man cheated on you and I said “he’s wired to spread his seed” you would not be accepting biology as a good argument.

  29. 59

    DMC @ 50, surmising that eveyone who reads this site and enjoys contributing and learning from the conversations has a less than satisfactory romantic life is not an absolute.  I have been happily involved with my guy for several years, but I dated a lot and enjoyed *most* of my prior relationships, even the ones that weren’t the forever kind.  We all make mistakes, men and women, but hopefully every relationship we have in life, however long or shot lived teaches us something. 

    As for reading these forums, I just find it very interesting, the dynamic between men and women, whether I’m happily loved up or not.  🙂  And althoughI certainly don’t think I’m *beneath* asking a man out (I’ve never felt I’ve HAD to, thank goodness!), but I enjoy letting a guy feel like a guy, and pursue me.  Evan is dead on when he says its largely ineffective for a woman to take away a man’s masculine edge by not allowing him to initiate a date.  As Heather and Michelle as well as myself have said, in our experience, confident men will take subltle signals of interest and ask a girl out if he finds her intriguing and attractive.  Simple as that really.

  30. 60

    The truth is that you men are WIRED to chase.
    Men might be wired to pursue. All people are also wired to be violent when afraid, pee wherever it is convenient and doesn’t get into food, sleep whenever we are tired, and have sex when the opportunity presents. Letting that wiring dictate behaviours isn’t attractive.
    This  ‘men are made this way’ and ‘women are made that way’ explanation for what are  effective dating behaviours for some people in some circumstances is way overused.

Leave a Reply

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