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).
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  1. 21

    I’m curious about that 25%-75% split, because it coincides with the “out of thin air” figure for the split of introverts-extroverts.     A lot of people make the mistake of thinking that an introvert is just shy, or afraid, or whatever “beta male” stuff and I find that rather annoying.
    However, it turns out that when you run the statistics on people taking the MBTI test, you actually get marginally more introverts than extroverts, it’s a roughly 50-50 split; the low guess for their prevalence comes about because introverts, by the very nature of introversion, are less visible in society.     It may be that “guys who don’t always ask first” have a similar statistical balance that is masked because of their tendency to be less visible (especially if women are taught to believe that men will always ask first – that way you never discover how many are the opposite).
    What I will say is that 10 years is too long to wait: either by that stage you’re totally in his friend zone as well or he will have rvealed his hand in a negative way.     I agree with EMK in terms of the signals to look out for in the OP’s situation.     If you’re interested, there’s nothing wrong with letting a guy know but it definitely helps to be clear early on, because that way you both know where you stand and if it’s not reciprocated then friendship can develop normally (see reason #4 in the OP).

  2. 22

    Do men always ask out a woman they’re immediately interested in?”

    If a man is interested in a woman, he will will ask her out for sure given he  knows that he has a good chance with her.
    Men don’t like to be turned  down – and as a matter of fact, nobody does 🙂 –  so the more he is  certain he’s got  a good chance with a woman, the more likely that he will ask her out if he is interested.


  3. 23

    Amen to Helen! Being thoughtful about another’s feelings is key, and highly underrated.

    Good thing Angelina released the guy. He sounds like a real basketcase and remaining friends with someone like that will only waste her time and emotions.

  4. 24
    The InBetweener

    +1 – Those words in red are KEY!! Other than that, why risk it?  


    Do men always ask out a woman they’re immediately interested in?”

    If a man is interested in a woman, he will will ask her out for sure given he  knows that he has a good chance with her.
    Men don’t like to be turned  down — and as a matter of fact, nobody does    –  so the more he is  certain he’s got  a good chance with a woman, the more likely that he will ask her out if he is interested.

    1. 24.1

      No. The more he doesn’t even have to be sure of his own feelings or take any accountability.

  5. 25
    The InBetweener

    Interestingly enough, the words never manifested as red. Well, the words in BOLD.  

  6. 26

    Very good (and kind!) advice, Evan.  

    Angelina, this guy sounds like an immature manipulator. I totally agree with Helen, in that there are people out there (both male and female) who assume that all others will find their every thought fascinating. Blah blah blah blah blah. Meanwhile, you sit waiting patiently, politely, thinking your turn for “sharing” is just around the corner. Only it never comes, because in the end — it’s all about them.   

    That is not a friend. In real friendships, it’s a 2-way street. You share, you inquire about the other person’s well-being, and then you shut up and listen. In other words, not only is this guy not boyfriend material, he also sucks as a friend. And not only does he not deserve you as a girlfriend, he doesn’t deserve your generous friendship, either.

    I think there is a #5 Guy Friend Scenario, and that’s where the guy wants your friendship because he knows you’re at least somewhat attracted to him. So he throws out a hook once in a while to see if you’ll bite, to make sure he’s still “got it.” He doesn’t want  it to be platonic, but he doesn’t want to be your boyfriend either. Do not give this guy your open ear or your friendship. He’s already misused it.  

    And as Evan said, no point beating yourself up about your query. After 10 years, good god, something had to give. You’re certainly not the first woman to ask for clarity and then regret she ever asked. Let it go. It’s time you devote that energy elsewhere, to yourself and to finding someone who can be a grown-up, equitable partner. Best of luck.   

    Oh, P.S.   I also don’t believe the 25% statistic about shy guys, pining away for you but just can’t bring themselves to utter the words, “So, want to go out on a real date?”   If they’re out there, I sure have never met one.

    1. 26.1
      Evan Marc Katz

      Obviously, I made up the 25% shy guys statistic. But it’s based on my years of experience. There are MILLIONS of guys whose existence you don’t even acknowledge. They’re not great looking. They’re not charismatic. They’re not extroverted. They rarely, if ever, talk to women, much less go on a date, much less get laid. I’m not saying you should WANT these guys; I’m saying that they exist. If they didn’t, there wouldn’t be a multimillion dollar market for pick-up artists – one designed to teach men to have confidence with women. Just because you don’t notice these men in your day to day existence doesn’t mean they don’t exist. They’re probably home right now playing video games.

      1. 26.1.1

        You are very right Evan. When I was younger, I was part of the 25%. It took me an enormous amount of work, many, many hours of effort to where I am today. I’m certainly not a master pickup artist, but I have gotten better than I was.

        And yes, women considered me completely unattractive and invisible.

  7. 27

    I can understand how Angelina feels, was in the same position about 2 1/2 years ago.   A guy I had known for years, who’d attended my wedding, fought with me like cats and dogs about stuff, but overall was a good friend, started asking to hang out with me more often, talked to me more online and by phone.   By the end of 2009, he’d made his feelings very clear: he’d always wanted to date me but for the majority of that time, I’d been engaged and married, and then met someone else not too long after my ex and I split.   I had some misgivings about the situation (and I really should have listened to those misgivings) but I started dating him anyways.   What a disaster.   He became verbally abusive, rude to my friends and family, controlling.
    I ended up breaking up with him after one tantrum too many in which he sounded just threatening enough to make me wake up and smell the coffee burning.   But because so much damage was done, it ruined the friendship.   I cut him completely out of my life, he blocked me on Facebook, we have nothing to say to each other.   I totally misread this guy and fell for his lies, and boy did he tell me a whole lot of whoppers!  
    Thank you for posting this, Evan, it makes me feel like there are people out there who’ve been there and done that and can relate!

    1. 27.1

      yikes! Sounds like you dealt with that about as well as you could have.

      what can you do when there are lots of big lies involved?!

      You gave him a chance , it wasn’t good and you managed to get away.

      I’m quite impressed by this short story.


  8. 28

    Bravo Angelina!! I had too cut of my ex (an ex-colleague, turn friend) out. I been through similar situation like yours. To make things worst, we flirted, hugged & kissed like couples do, only to realise that he just want to treat me as friend. After the “initial break-up”, I do intend to get him back but he was rather cold towards me. After I had “disappeared” for some time, he started texting and his text starts getting flirtatious. Since I had made up my mind to cut him off, I had not replyied to any of his text. The last text I receive from him is him wanting to invite me to his wedding. I can’t believed that he is that naive (knowing him, he’s not) to believe that we can still be friends. I don’t wish to be invited. Till now, I’m proud to say that I had not respond to his invitation.

  9. 29

    Well, I certainly don’t think that a man *always* asks a woman out if he’s interested in her.   That much we’ve pretty much establislished, for various valid reasons.   What I do think in this particular case though is that the man in question sounds like an insecure, game playing jackass!   He’s been friends with this woman for ten years or so, with what appears to be some undercurrent of attraction from both sides, he tells her how hot she is and how he’s fantasized about her?!   Good grief, how much more blatant does it need to be that he’s either interested, or a total game playing waste of her time?  

    Frankly, this doesn’t even sound within the realm of normal behavior to me.   I would be turned off mighty quickly if a man behaved this way towards me, and then never went so far as to ask me out or display some honesty and integrity  in his intentions.   They’ve known each other for years, for Pete’s sake, and are not just aquaintences.   This is weird, IMO, just plain weird and dysfunctional.   To the woman, I’d advise, please, pretty please, for your own sanity, move on and let yourself be open to a real relationship  when the right guy does come along.  

  10. 30

    Why do posters here keep saying that the friend “led her on”? He probably said all those things (she was hot etc) to make her feel better about herself after one relationship disappointment after another, and after she started questioning her attractiveness to men. This is exactly why it is tricky for men and women to be and stay “friends” if they are both hetero. Any kind of overtures might be interpreted the wrong way. Negotiating this minefield is why many men don’t even bother being “friends” with women unless they already share a history (or some sort of bond) and it is abundantly clear to both of them that romance is never on the cards (eg. exes, cousins or other close relations, friend of parents or children, teachers or students, parent or child figures etc). I don’t think a lot of men, if they are honest with themselves, will become and stay “friends” with women they are attracted to (sorry Evan). I don’t think these honest men will want to put themselves and their female “friends” (whom they are attracted to) in a position where things could get awkward and embarrassing – say she moves over for a hug and she feels that you feel something – you know what I mean.
    The thing with Harry and Sally and Jamie and Dylan all those other man-woman buddy stories you see in the movies is this : These “friends” were already in romantic relationships but they just didn’t know it yet, hence the comedic element.
    This is not to say absolutely that men and women can’t be friends if they are attracted to each other, except that it is very very very very very rare.

  11. 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.”

  12. 32

    @ Heather #27:

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

  13. 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.”

  14. 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.

  15. 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.

  16. 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.       

  17. 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………

  18. 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.   

  19. 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.

  20. 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.  

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