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?

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  1. 91

    I think Ray is pointing out the dance aspect of all of this. Fairly often in my experience, there’s been a period of time where things are up in the air. Perhaps both of us are aware of the interest in the other, or perhaps that interest isn’t clear on one end. In either case, a move hasn’t been made yet, and that can be unnerving.
    In my view, it’s most important to consider timing. Moving too quickly can push away anyone, and obviously moving too slowly doesn’t work either. What’s too quick and too slow depends on each person as well. I remember waiting several weeks before asking out one woman I dated because it seemed like the right approach for where she was at. Which makes me wonder if sometimes what women are experiencing when asking men out is simply moving too quickly. Not everyone leaps at going on a date an hour or two after meeting someone.

  2. 92

    So we’ll agree to disagree that male and female inbred, reptilian brain instincts are ‘stereotypes’, although I never said that.  What I would love to hear, since there is no fundamental difference in males and females, why in general boys like to play with ‘boy’ toys, like trucks and in general girls like to play with girls toys like dolls.  Those must be stereotypes too, just like the radical feminists claim.  Anyone who is a parent can immediately see that’s not the case.

    Funny too how on one hand there are those here who say society has changed men and women so much, but on the other hand society isn’t going to change until one of us do.  We’re talking thousands of years here of societal changes and there fundamental differences in men and women that have not changed at all.  Again, once one raises kids, I think a lot of this becomes very apparent.   

    Perhaps the reasons it doesn’t work out is because you’re too much in your masculine energy, and ultimately, that’s a turn off for the men?  Just throwing it out there…there usually are other factors, timing, personality, etc.  A man will NEVER say this is the reason he becomes disinterested, he just doesn’t know why he doesn’t feel it.    

  3. 93

    Betsy, yes both men and women in the past have faced threats equally, but it has generally been men having to deal with those threats head on. Men are the first the go into battle, with women only being forced into self defence as a last resort when all the men have been killed. Even the “celebrated” Israeli army does not send its women fighters direct into battle in the first instance. Mainly because historically women have been pregnant a lot of the time and men have generally been more physically capable of battle (higher muscle to fat ratio as fat is necessary in women for estrogen to function properly and for fetus incubation purposes). In facing any threats head on, society generally sends out its most physically capable individuals first. It make absolutely no sense to send your women out to fight the enemy’s men unless your women are seven foot valkyeris facing off three foot tall pygmies from the kalahari.
    Michelle, yes what you have observed is correct. Generally men’s brains behave in a different way – generally of course since there are always exceptions. A friend of mine who is a stauch feminist gave her son dolls and her daughter trucks to play with. Guess what happened ? Her son’s doll became superman, fighting evil and engaging villains to battles to the death. Her daughter’s trucks spoke to each other, were friends, went on cute social outings and had “relationships” with each other.

  4. 94

    [email protected]

    You are assuming it is the man who decides not to proceed in those situations… that isn’t always the case.  In fact, it isn’t the case most of the time. 

    Why do boys play with trucks and girls play with dolls?  Because that is what their parents buy them.  That is what they see on TV and what they see other children near them playing with. 

    If a boy played with dolls, he’d be ridiculed and shunned.  Girls who are ‘tomboys’ are equally shunned.  That’s not biology.  It is socialization. 

  5. 95

    “A friend of mine who is a stauch feminist gave her son dolls and her daughter trucks to play with. Guess what happened ? Her son’s doll became superman, fighting evil and engaging villains to battles to the death. Her daughter’s trucks spoke to each other, were friends, went on cute social outings and had “relationships” with each other.”

    Valuable lesson learned!

    Men are about death, women are about life.     

  6. 96

    [email protected]

    Good for them.  I hardly think your one example is indicative of the entire male or female gender.  I could give you plenty of my own… starting with me and the things my parents gave me to play with growing up… in addition to their reactions to what I did with those toys… but I suspect it wouldn’t matter.

    You appear to believe we are slaves to ‘biology’.  I don’t.  We’ll have to agree to disagree.  IMHO, biology might be informative, and that’s nice.  I don’t tend to refer to it as an excuse mechanism. 

    Once upon a time, people also believed the sun revolved around the earth, that black people’s brains were smaller (so were women’s) and that we should be ‘bled’ when sick to drain out the disease.  All of these have been shown to be debunked, of course. 

  7. 97

    Back to the topic… I agree that asking a man out in general probably isn’t useful or productive most of the time.  However, I’ve also learned that it is the exceptions that make life the most interesting…

    I’m for trying all avenues.  What’s it going to hurt really?  If it doesn’t work, try something else.  Big deal.  I’m ok asking men out, or learning how to do it in ways that are appealing.  I feel I’ve accomplished this most of the time.   

    When I was online, I did almost all of the initiating, and rarely or never responded to men who made first contact with me.  The ones who made first contact were usually just attracted to the pictures and had nothing else going oon for him. 

    At some point,  I decided to stop wasting my time plowing through gobs of unwanted emails from spammers who liked my pictures, and wasting my time reading well-intentioned emails from men who had a ‘system’ that makes it LOOK like they read your profile or give a crap what you actually think… (go on a date with them and see how much they REALLY read… not much!!)   

    Nope, I shucked all that, pulled down my pictures… and spent my spare time going after the ones who I seemed to have genuine compatibility with at a personal level.  The quality of my interactions went WAY up after I did that.  Still, I had to exit online dating because, in spite of all that, there are waaaayy too many men there who just aren’t ready or looking for a committed relationship… nor do most of them have the kind of character I’m looking for.  Cheaters, recovering alcoholics, bankrupt, toxic relationships with ex-wives… yuck.  Too much trouble sifting through all that.  I’d rather meet someone in real life… where most of that is sorted out through other filters…

    Anyway, long post, I know.. but I just wanted to share with the other women how much MORE successful my interactions became once I did some careful initiating.  And especially for those of you who happen to be above average in the looks department… I realize it can get REALLY old dealing with the spammers and the disingenuous.   Save your pics for the ones you choose yourself… or choose pics that are the less attractive (yet still appealing) versions of you.   You’ll be attracting men of higher character, IMHO.     

  8. 98

    @100 Men are about death
    This is the most offensive, sexist generalization I have ever seen. It is even worse than saying “all women are stupid.” In four words you have said half of humanity’s reason for existence is to kill and destroy.

  9. 99

    I find it very interesting the type of people this blog attracts. What I have found is that ‘birds of a feather flock together’. There tends to be very little understanding of nuance, nor is there curiosity.  Although I did laugh out loud at #103 because it has nothing to do with anything.

    Men ARE all about ‘death’.  When we were in prehistoric times, they went out under very harsh conditions to gather food for their families–know they would be facing death all the time.  Throughout history, it’s primarily men who go to war–do you think they don’t know they could possibly be giving up their lives as a result?  In the U.S., the military is voluntary.   In today’s world, what do you think sports is?  It’s the ‘death’ of the opponent metaphorically.  Men still VOLUNTEER in the U.S. for the military.   In many stories, fables, tales, the man goes off as a hero, and hopefully returns safely, but often goes understanding he may die (and it’s the woman who send him off on his journey).  I could go on an on, but I won’t.

    Obviously  this is a lofty intellectual concept.

  10. 100

    Ever see an egg chase a sperm?   End of story as far as biology goes.

    Society, though, sometimes advocates different behaviors than biology.  

    Many men are comfortable with the biological approach; women who want these types of men need to act like an egg, be receptive to them. 

    Meanwhile, certain men prefer acting like eggs not sperm, and wait for women to chase them down. 

    Decide what type you are and see what works.  

  11. 101

    Michelle, it is more accurate to say that men are less risk-averse than to say that they are “about death.” And it is not as though it is such a simple dichotomy: “men are about death, women are about life.” In your own examples, the men who hunted food and fought in wars braved death, yes – but for the purpose of preserving the lives of others. 

    Historically, because men were generally physically stronger, they were used in society in ways that were meant to defend; whether against other humans, predatory animals, or harsh weather conditions. It is no wonder men evolved to become less risk-averse.  This is something that has benefited society AS A WHOLE, including the women in it.

    No wonder AllenB took offense to that comment.  There is no need to laugh at him or to suggest that these concepts are too “lofty” for him to understand.

  12. 102

    Women aren’t more risk averse than are men. Before mid-1900s, getting pregnant was a mortally dangerous proposition, given the high rate of maternal deaths in childbirth. Yet women have always taken on this risk. Since more people are born than die in wars, I’d say that women have carried more than their share of the risk-taking throughout history. This willingness to bear children despite the possibility of death has benefited society as a whole much more than fighting in wars, I’d say.

    And most of male “protection” of women has been protection against other men. A woman was a man’s property that other men were out to take or defile or destroy. While I’m glad that my female forebears were protected property long enough to procreate, I’m not sure why we have to romanticize this historical fact or use biology as a justification for it.

  13. 103


    That is not true.  Pregnancy does not qualify as a high risk activity.  The majority of women did not die during child birth even in centuries past.  Men have shorter life spans than women and have always been the ones charged with doing the most dangerous jobs.  War, sailing, exploration, building and mining to name a few.  Men are more likely to die in accidents.  All men didn’t view women as property.  many men of ancient times wrote heart-melting love poems about women.  Its annoying when feminists keep trying to rewrite history.

  14. 104

    [email protected]: Not sure where you’re getting your info from, but it is inaccurate.

    1) In colonial America, for instance, a woman’s lifetime chances of dying in childbirth were 1 in 8.

    2) The love poems you’re likely talking about were part of a literary tradition called “courtly love,” where a man of the court singled out a woman of the court to act as his muse. These relationships were not consummated; the woman in question was often the wife of a nobleman of higher rank than the man who was writing about her. He did not actually have a relationship with the object of his desire.

    You can google “childbirth” or “maternal death in childbirth” and “courtly love” if you want verification of what I have just written. Has nothing to do with feminism or rewriting history.

    And more stats:

    In England, 1700-1935, the estimated rate of maternal mortality in childbirth was 25 in 1,000, or 25,000 women annually. That’s 5.875 million women dying in childbirth in England alone during the time period cited above.

    You can verify the maternal death stats I use here:
    Women were also killed in the course of wars and continue to be to this day, despite the fact that they usually have nothing to do with starting the wars.

    Again, nothing feminist about this, though reading this stuff is making me turn in that direction.

    1. 104.1

      Ah, a mind.. thank you.. nothing like a good mind..

  15. 105

    Greg 108: Pregnancy isn’t an activity. Maybe the reason that you don’t see it as high-risk is because you don’t ever have to even think about going through it. Having been through it myself, the idea of giving birth in the conditions that women put up with for eons is positively terrifying. And to do so when impregnated by a man for whom you were just property, something to carry on his name, is really horrifying. Consent was not a concept in marriage until recent decades, either. So it’s not like women had much say in whether or not they’d take on the mortal risk of having a child.

  16. 106

    OK childbirth mortality rates were higher.  Big deal.  So were the mortality rates for every other disease.  Black plague?  I guess life must have been altogether terrifying before modern medicine.  Some of the women on here are so bitter.  I’m pretty sure women enjoyed life before the 20th century.  Some of you act as if all men in the past beat their wives and viewed them as property.  That’s ridiculous.  There’s always been good and bad men. Many men deeply loved their wives.  Even in the Bible which was written centuries ago, men are told to continue loving their wives not becoming bitterly angry with them.  So ancient texts do show that some men did love their wives and some wives loved their husbands.  Men haven’t changed much throughout recorded history.  Good men who loved their wives treated them well, just like any normal human being would do.

  17. 107

    Greg 111: It isn’t about men being “good” or “bad.” How we understand what is good or bad behavior is determined by our society and culture. In the 17th century a man would not necessarily be considered a bad husband for beating his wife. And especially not for having sex with her against her will. The notion that a husband can assault and rape his wife is very recent–some states didn’t define spousal rape until the 1970s, which meant it was too bad for the woman if she married a guy who wanted it and she didn’t and he was going to force the issue. And the idea that marriages should include romantic sexual attraction didn’t come into play until the early part of the 20th century, reaching its apex in the 1950s. 

    The word “love” as it is used in the Bible isn’t talking about romantic love, the way we do today. This is a translation issue. And again, even in Biblical times, a man might beat his wife and still think that he was not doing anything wrong. In Biblical times, a woman would be stoned if she were raped, just as it happens in Afghanistan today.

    The people who are responsible for clarifying and educating people about the human rights issues regarding the treatment of women are what you would call feminists.

  18. 108

    I’ve been in a similar situation and actually told my friend about my feelings. He told me that he did not see me in that way and then 1 week later we were out a social event and we spent most of the evening together snogging! So I asked him afterwards about the mixed signals and whether he had changed his mind but he said that he could not see us being ‘married’ in the future. We are no longer friends because despite knowing the way I felt about him (and I took the rejection on the chin) he took advantage of the situation – so I guess he really could not have been a good friend in the first place!

  19. 109

    Betsey your really reaching.  I don’t think anyone can confuse love and beating, especially when the same passage told men not to be bitterly angry with their wives.  Also they were told to assign honor to their wives and to love their wives as their own bodies.  Obviously you are not familiar with the Bible.  
    My point here is not to provide a religious sermon but to to point out that treating women well is not some sort of modern invention.  Women’s rights does not equal women’s fair treatment.  There have always been good men who treated women well and bad men who abused women.  The same is true even in modern liberated societies.  Domestic violence still exists, and sadly some women even stay in such abusive relationships of their own free will.  Women are still objectified and treated poorly, even in America.  If that weren’t the case then there wouldn’t be all the male hatred and bitterness in this forum.  The point I’m making is that there will always be men who mistreat their fellow women and men who don’t.  I don’t feel that you can argue that women are better or worse off overall n the 21st century.  I personally think that things are about the same.

  20. 110

    Greg 114: Actually, I have studied theology and Christianity extensively, along with both living and dead languages, and history.

    The Bible doesn’t say anything about loving your wife except in the New Testament where husbands get the vague admonishment to love their wives as Christ loved the Church, however you want to interpret that.  You get a lot about wives submitting to their husbands, though.

    I do agree with you that there have always been people who have treated other people well. It just hasn’t always been law or practice for men to treat women well, if you believe, as I do, that treating someone well means as equals and as an autonomous being who gets to choose her own fate. I find it disingenuous to suggest that men have treated women well historically. Just as it’s disingenuous to suggest that African slaves were treated well by white slave owners. Were all slaves killed and maimed and raped by white slave owners? Probably not. But the mere fact that that law allowed a white man to own a black person and do whatever he wanted without punishment was enough to terrorize an entire subsection of the population for generations, and that legacy continues. We all have to deal with that, still. 

    It’s the same way with women. A husband had complete control over his wife and children. Whether he exercised that control or not, or to what extent he was abusive, has little bearing on how having no say in your life has affected women as a group. And again, there are legacy issues from this.

    Done with this discussion. Best of luck to you!

  21. 111

    I was not saying that women were treated well historically.  I was just pointing out that there are always good people and bad people.  Making laws and giving people “rights” doesn’t change people hearts.  When slavery was abolished, bad people found new ways to mistreat people.  Likewise making it illegal to beat women won’t make a bad man love women.  Instead of beating his wife a bad man will verbally abuse her.  So just because women now have “rights” doesn’t mean that they are as a group better off.  Especially when some women still choose to be in terrible relationships.

  22. 112
    romantic ideas

    what kills me here is the comments, why all the arguments? Men and Women are different. We’ve known it for a while now chaps. Let’s all be friends and enjoy life and all that goes with it. Love each other and love life!

  23. 113
    Margaret Thatcher

    Great. So now women are being told not to pursue, and men seem to be becoming UNWILLING to pursue…where is this going to get us as a society!?
    Reminds me of the middle school dances where boys stood on one side of the room, and girls stood on the other side, each facing the giant empty void in the middle.

  24. 114

    Greg @116: Yes, women as a group are better off with rights. Give up yours for awhile and then we’ll have a discussion.

  25. 115

    Sometimes a guy can think highly of a woman without wanting to actually be in her life. Especially in the case of a long term friendship.
    Angelina knew this guy for ten years which meant that a lot of information was shared between them.

    And either the guy learned something about her that did not match his goals, or the time had passed where he was attracted to her, or he enjoyed the friendship so much that he did not want to take things to a more complicated level in a romantic relationship. Or that if they do date and break up , their friendship may suffer and he would lose her.  Course in this case he did but he may not have expected that.

    Have lost several wonderful female friends because of this situation. 

    I do not think the guy was intentionally sending mixed messages, he just felt that he could share intimate thoughts with a friend.
    One of the posters said emoting everything might be inconsiderate.
    But is that not what a good friend does, listen and share the deepest things no matter what they are.

  26. 116

    I agree with everyone else that says that 25% is a tad bit too low.  I don’t know if I’m too impatient or I’ve dated shy men but in my past I’ve been the one that goes after the relationship.  My husband and I watched each other from afar until I decided to make the first move.  I believe a man will go after you if he is looking for a “good time” but becomes shy when he is actually interested in a relationship.

  27. 117

    If he cannot approach me ask me out, then I do not want to date him! Gee, how wonderfully convenient. Let women taste some of this rejection and they will change that tune!

  28. 118

    I will briefly return to the topic of asking out. In my opinion, it doesn´t matter so much who does it. What matters more is whether it is done in an appropriate way – politely, not aggressively, etc. – and at the right time – when you feel that the other party will accept. I don´t understand the whole “science” concerning askig out. E.g. my boyfriend didn´t even remember when I asked hm which of us had initiated the first date, he said that he had been looking to seeing me and that was all that mattered. I like the idea of relationship as “tango”. Yes, the man leads, but sometimes the woman makes moves she wants to make and it doesn´t harm the whole dance, or does it? When two right people meet, all these things are irrelevant, but of course, I understand Evan´s advice because he just wants to prevent people from being unhappy in this dating game.

  29. 119

    I think that timing is also a huge factor. I have a friend who I have feelings for. We met thru a mutual friend about 9 months ago and although we currently live in differentcountries, we talk almost every day by phone. I stayed with him recently when I returned to my home country for a visit. He is visiting the country I live in in January. We have a great connection, laugh constantly and are so relaxed in each others company. When he comes here, we are going away for a weekend. Despite the connection and the flirting he says we are better as friends as he doesn’t think long distance works. I am due to return to live in my home home country next year and am waiting til then to see what happens.
    I do believe that timing has a lot to do with whether or not we get together. If he still wants friendship instead of a relationship then I have to decide what I do next……back off or stay as friends. Hoping it’s about the timing! 

  30. 120

    Another reason: he’s in a ten year relationship with a man and cant tell you about it, but hooks up with other random people, mostly men during this time and enjoys spending time with you- especially since it makes him appear straight. He may later come back to you, claiming deep love and stating that he is bisexual. After, ofcourse, the other guy breaks up with him and he decides he wants kids. This happened to someone İ know. Stay strong, and dont question too much why its not working out. You can later decide, if he comes back, if this relationship is good for you.

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