Should I Ask Out The Man I Just Started Dating?

Should I Ask Out The Man I Just Started Dating?


First off, thanks for all the info online and for “Why He Disappeared”. Every time I start to obsess or get emotional now, I take a deep breath and go reread your book.

Last weekend I went on second dates with two men that I’d met online. On one of the dates we had lunch. He asked. The other date, I broke the mirroring rule. When I purchased tickets to the symphony a month ago I figured I would just end up dragging my son along with me. Instead I invited one of the guys a couple of days after our first date. We went, and we had a good time.

Now I’ve just gotten GREAT free tickets to a local concert that I know both men would enjoy. These are VIP box seats with preferred parking etc., and the concert is Saturday! I haven’t heard from either man since the weekend and, while I’m not bothered by this, I don’t want to go to this concert alone (alas, not something I can drag my son to this time).

How do I let the man be the aggressor and how do I mirror while dating when I’m the one with the tickets all the time?

– Meredith

To everyone who hasn’t yet read “Why He Disappeared”:

If he calls, call him back. If he texts, text him back. If he says he wants to get together with you, say you want to get together with him.

a) You should.

b) It introduces a not-so-revolutionary concept that I call “mirroring”. Essentially, when you’re starting to date a new guy, the best thing you can do, to see if he’s genuinely interested in you, is to simply react to what he does. If he calls, call him back. If he texts, text him back. If he says he wants to get together with you, say you want to get together with him. And so on.

The reason that mirroring is so effective is because it honors the way that most men choose to pursue women. We are — in general – much more comfortable with us winning you over than we are with you chasing us down, asking us out, making the first move, and getting down on your knee to propose to us.

This doesn’t mean being arbitrarily difficult or challenging. You should always be warm, receptive and available. You should just follow his lead, that’s all.

Because when you don’t follow his lead — when you start initiating contact and asking him out for dates — you never actually find out how he feels about you.

If you’re doing the initiating and chasing, he may just be enjoying your company temporarily.

Which brings us back to you, Meredith.

You can call up one of these guys and offer him free concert tickets, but is he going out with you because he likes you? Or is he going out with you because he likes music? Or because he’s bored and had nothing better to do that night, so why not take in a free show and maybe make out with you afterwards?

You don’t really know, do you? And you can’t know unless you sit back and let him choose you. If you’re doing the initiating and chasing, he may just be enjoying your company temporarily. But if you do nothing, the only way you’ll hear from him is if he’s genuinely excited and motivated to pursue you.

Finally, the key phrase in what you wrote is this: “I haven’t heard from either man since the weekend”.

And there you have it.

That tells me everything I need to know about how much these men like you.

I don’t know exactly when you wrote this letter to me — was it one day after your latest date with both of them? Three days? One week? All I know is that if it was much more than one day of silence after your date, he’s probably ambivalent about you. Which means that you could ask him out and he may say yes, but it won’t mean much of anything until you let him ask YOU out instead.

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  1. 81

    Julia 59 and Selena 67. I get the point about seeing a man not responding after a few dates as a sign of lack of interest. When I think about the times I have tried to gauge a woman’s interest after X number of dates early on, it’s never been a total disappearance and wait for her to come to me act. Usually, it involves shifting the level of contact between dates. Instead of rushing to set up the next date, I might wait a few days to see if she makes any attempt to contact me. I have occasionally done what Selena’s guy did and say something directly about her lack of contacting me, but that depends upon the level of contact as well. If you’re talking in some form every day, you’ve developed enough of a connection where a guy could say something more directly in a way that doesn’t seemed forced, needy, or controlling.
    A lot of the dating situations I’m thinking of involve seeing someone, then having a week pass with little contact in between, and then going on another date. After another date, then there might be a call or an e-mail in between to say hello and how’s it going. The point being that the contact is slower in build up, and so it’s more difficult to say anything directly without it seeming forced or odd somehow. The majority of dating situations don’t go from you’ve never met to talking to each other every day, so I think it’s more difficult for a man to successful pull off deliberately changing a dynamic like this. It’s safer to either keep stepping up and hoping she’s really into you, or doing more subtle things like I mentioned above. Since many men are, as Barry points out, terrible at subtle, they mostly keep pushing for dates until it’s made totally obvious to them that the woman isn’t interested.
    Julia 59: “The problem with pulling back and testing is that it upsets and established order that you’ve created by initiating with a woman. Why would a woman with any dignity respond to a man who pulls back by pursuing him.” First off, whether dignity is involved depends upon the nature of the “pull back.” There’s a wide spectrum between total disappearance and pushing for another date the moment the current one is over. Secondly, I see this “established order thing” as similar to the man pays for dates thing. It’s being done as much to follow social expectations as to demonstrate real interest. I can ask you out again every time early on, and still lose interest once I get to know you better. I can make it really easy for you to show up and have a good time with me, and yet I may end up only wanting sex. As you pointed out, dating in our generation and younger generations is more tricky, and I’d say for a variety of reasons, good and not so good.
    Overall, I think the best way to approach dating is to combine being who you actually are with some level of experimenting. So, for the outgoing woman who has had little luck with being the initiator, it makes sense to employ mirroring, as long as she doesn’t, in the process, end up hiding or giving up her strength and desires in the process. And for someone like Kathleen who recognizes that she wants a man to lead in the relationship, then certainly mirroring is going to be valuable. The difference though between experimenting and following rules is that you pay attention to results, and make adjustments based upon variable conditions. Evan advocates mirroring because of the results his clients have had. I’d argue his clients are a very particular subset of women who tend to both be outgoing and financially successful, but also want men in the lead of their relationships.

  2. 82

    @Barry – I understand what you are saying. The only thing I feel sure I’m responsible for is my own reality. I am not there to ‘fix’ men who have otherwise given up on women. I feel sorry for what they’ve experienced. But I disagree with what you are saying. If I come across a man who lacks trust in women because of past experiences, then I think it’s his issue to deal with. And I’m not gender biased. I’d say the same about women. Men should not feel responsible for women who’ve lost trust in men because of bad experiences in the past.

    Your point of view appears to very black and white i.e. “Men may develop thick skins, or they may just commit suicide.” I don’t think it has to be like that. I’m not sure I’ve developed the thickest skin for rejection. But I don’t care. I acknowledge that I’m human and that I will feel weak sometimes. I acknowledge that my emotions are the way they are. When I think it those terms, it makes me feel less afraid. I got there through CBT. I learnt to think “Okay I might be rejected. But is it really as bad as I’m imagining?”.  

    You read too much into newspaper articles too. It isn’t fact. If you can’t read those articles without getting upset then don’t read them at all. You can only work that stuff out by looking at your own life anyway.

    I confess to not self-identifying as a feminist. Still I wouldn’t use gender-loaded terms like “man up” although I do tell myself to man up sometimes!   I don’t think I have unhealthy expectations of men but will give what you say some thought. It always helps to hear insight   from the other side, and that is why I read this blog.

  3. 83


    Hear what you say. Of course it isn’t black and white.
    I know plenty of men who have essentially given up, and I know that their options would improve if they changed their mindset.
    Doesn’t alter the fact that they are screwed.

    Frimmel makes the valid point that the reason women like Fiona cannot find peers is that they have taken the men’s jobs.This is what the newspaper article surmises.
    The data comes from the Office of National Statistics though, so is pretty accurate. A very fast increase in men unable to find partners.

    I think the thing to watch out for is men approaching women expecting to be rejected. Insufficient positive feedback may be interpreted as lack of interest.


  4. 84
    serena grace

    I also see a plethora  of middle age men in the U.S. having no luck finding a partner…. They’re the guys who consider women 10-15-20 years younger and 50-75% better looking than themselves as their target range….

  5. 85

    I don’t mean to proffer wisdom as a PUA rather empathize with you and share how I managed to change, as I have been through the full gamut of emotions you describe. I (and probably all men) have experienced the pain of rejection, the despair, despondency, depression and self-doubt (partially) due to no luck with women.

    However, women are not the problem. The vast majority of women are kind, decent people who just want to live a good life, be respected and to love and be loved. They really don’t want to hurt men. Yes some of them have unrealistic expectations but so do many men (myself included).

    “I know that their options would improve if they changed their mindset”

    You’ve already acknowledged that these men would do better if they changed their outlook, and through good diet, regular exercise, sufficient sleep and being positive one can change their mindset. Allied with these steps I go easy on the booze, read the news sparingly and cut negative people out of my life.

    As Lucy said, no-one else’s behaviour is responsible for my emotions. I am solely responsible for how I feel.

  6. 86


    “It is easy to blame men for not “manning up”, but the truth is that there has been a social revolution and women’s increased demands and expectations can no longer be met.”

    What you said above is true to a point. I’ll only add this:  when you have a lot of women who openly express their intolerance for the male of the species, and say without hesitation that NO man is ever  good enough for them, then none of us should be shocked that gender relations have hit an all time low.      

  7. 87


    Thanks, however it isn’t my problem as I’m actually very  successful  with women !

    However that doesn’t apply to most men. Women’s attitudes are resulting in millions of men going without. Women ARE the problem, and if they are not why the phenomenal increase in single men living alone?

    1. 87.1

      Men who are actually successful with women, generally do not hold the toxic opinion of women that you do.

      If you (and the men you associate with) think women are exclusively “the problem,” then you are all better off not dating women.   The women (whom you solely blame for your dating problems – because it can’t possibly be YOU, right?!) are probably better off with a dating pool of men who don’t blame them, too.

      Sorry for the sarcasm, but when men blame all women, everywhere for all their dating problems, I have to say:   There are 3.5 BILLION women in the world.   We have different looks, likes, opinions, values, personalities, etc.   If you and your friends have been consistently unsuccessful with women (which is what it sounds like, despite your protestations that you are good with women), the common denominator is YOU.   Please don’t blame all of womankind, just because you make a lousy date.   Thanks.

  8. 88

    Barry why are you on here if you are so successful with women? Just to attack women? You think women don’t suffer rejection? I can’t count the number of men who told me they didn’t want a relationship. Last night I had to see a male friend I had been getting closer to for months go off with one of my girlfriends. Then I had to hear one of those poor but ever so lovely middle nen you refer to ask another male friend if he would be taking me home because he fancied a go. I left in disgust. If only that sort of thing were an isolated incident -it isn’t I’m afraid and I don’t feel if such men end up alone.  

  9. 89

    @ Barry #88

    “if they are not why the phenomenal increase in single men living alone?”

    For the answer, go back and  read serena grace @ 85.    

  10. 90

    @ Justine 90 & Serena 85:

    When I was having my losing streak through my 20’s (in college)  & 30’s (beyond), believe me, I wasn’t chasing women 10-20 years younger than me.

  11. 91

    I guess I’m stepping on a few toes here.
    But it seems fair to put the man’s view.

    You think I’m such a Wus that I should just validate all your “there are no good men” nonsense.
    As Evan says, you never hear men say there are no good women.

    No, women are beautiful, affectionate creatures, and men value them and want to be with them. Its  just that women make very stupid dating choices.

    Fiona, I am really sorry about the rejection you experienced the other day. I know it hurts. I lost someone I deeply loved to a ‘friend’ and the trauma was so profound   it took years to get over it (if I ever have).

    However I did point out that  focusing on Mr Rich would lead to heavy competition from your sisters who would give no quarter in their eagerness to obtain the prize. Please go back and read it again.
    I say again, would it not make more sense to be open to   men who actually want you ?

    And to justme and grace, I can only say I know many men who are single but do not want to be and they all have one thing in common.  
    But since a few are in their 20s, clearly its not because they are holding out for much younger women !
    You know what the article (written by a woman by the way) said.
    I can only assume you are in denial.  

  12. 92


    I think your comments are well-intentioned, but they make me  feel a little angry.   If there is one inescapable impression that reading this blog leaves you with, it is that there are indeed many lonely and heart broken women  as well who would love to find someone.   Please do not bemoan the chronic state of lonely men to the exclusion of all else and imply, no explicitly state, that women are the problem.

    For every man who has experienced a woman who should give him a shot and doesn’t want him, I can *assure* you there is a woman in the same position.  

    Do you realise that you cannot have a certain  number of single and alone men without having an equal number of single and alone women, since men and women exist in more or less equal proportion in the world?

    I am not saying that there aren’t many things that can be done about this, and your suggestion about being open to people who want you is very valid and good advice, but please don’t imply to us that women who can’t be pleased is the sole source of the problem.

  13. 93

    My apologies Barry, I incorrectly inferred that you had issues with women and rejection.

    “women ARE the problem, and if they are not why the phenomenal increase in single men living alone?”

    Well some men choose to live alone, but I accept that many men of all ages are living alone but would rather have a partner.

    However, the universe doesn’t owe men sex. The universe doesn’t owe men or women a relationship. The onus is on each individual to improve themselves and go out and create their own reality themselves. That is what the women on this blog are doing — laudably.  

    Unfortunately I witness a lot of men wallow in self pity or turn to drink / gambling / drugs etc. rather than sorting out their issues. These issues are not the fault of women. Many (most?) women are surprisingly forgiving on a man’s appearance and job if he’s got his shit together.

  14. 94


    I understand your anger. I could have said that there is a breakdown in relationships that both sexes must bear responsibility for in equal measure.
    That would certainly be diplomatic. It would also be a lie.
    The article, written by a woman, said that there was an increasing number of single men caused by women rejecting the men.
    So I have clearly not come up with this idea in a vacuum.
    How could anyone come to that conclusion ?

    With greater equality, women’s expectations in the work place and life in general has increased. If anything, men’s expectations have fallen.
    These expectations spill over into the dating sphere. Women want better quality men, but now there are even less than before.

    We have a woman on this very thread, whilst bemoaning her single status, has stated that she will only accept men who probably represent less than one per cent of the total male population.
    Other women on the blog have commiserated with her plight.
    This attitude appears pervasive.

    I am not saying any more than Mickey or Frimmel, so why the anger ?
    Could it be because you suspect I am correct ?

    Tom10 – I agree we should take whatever action is required to be more acceptable. We cannot change the attitudes of the opposite sex.


  15. 95

    >> I am not saying any more than Mickey or Frimmel, so why the anger?   Could it be because you suspect I am correct ?

    No Barry, not because you are correct but because you appear to be placing one-sided blame.   Perhaps I missed context somewhere but are you talking about a certain category of women?   Or just women in general?   I am also not as angry or personally offended as I am puzzled about why someone so clearly eloquent as you is arguing such an absurd point.   It wouldn’t be diplomatic to say that both sexes bear the responsibility for the breakdown in relationships; it would be the truth.   I agree with you: women are to blame.   So are men.
    I didn’t read the article but I did see the bits that you quoted.   I didn’t interpret that as “women are the problem” but rather as “women want different things than they have in the past”.   If men are unable to provide what the women are looking for, it’s a two-sided problem, wouldn’t you say?   Women need to adjust their expectations and men need to improve the offering.   

    I would not also say that “women want better quality men.”   It’s just that the definition of quality has changed.   Again, I am not denying that women can be too picky, too difficult, too whatever but so can men.   For every woman who will only accept “less than one percent of the total male population”, there is another who would make a perfectly good wife to men who have rejected her repeatedly because she wasn’t enough.   Enough what?   I don’t know and she doesn’t either.   The world is changing rapidly, expectations are changing but the blame does not belong to any one gender.

  16. 96

    I agree with this article.   And also in my experience, men who say they “love it” when a woman takes charge, asks them out, etc are just confused about how they feel.   Perhaps they are starting to feel insecure about rejection so they think the solution is for the woman to come to them.   Some also pull away on purpose to “test” women’s interest to see how much she will do to get to them.   I’ve noticed this with a few guys… They would start out being the pursuer   and then out of the blue pull back.   When they did that, I would not contact them.   But eventually I hear from them and they’d be upset if they didn’t hear from me because I don’t initiate contact while they are in  withdrawal  mode! I’m like well I really enjoyed hearing from you and tell them I’m confused about the whole thing. then they express some sort of fear that I might think they are coming on too strong and that was why they didn’t contact me.   So odd.

      Whatever the reason is,   most men  who think women should be doing “equal pursuing”   subconsciously   are not attracted to women who do this.  Whenever I tried to initiate anything in the early stages of dating, even when a guy would flat out ask me to contact him and I’d follow through, it never worked out in my favor, especially when I did more than the guy. They’d either disappear or just saw me as a “friend”. And that is what I used to do A LOT.   The guy would act interested if I initiated, maybe thinking there was a chance we’d get physical or he just was bored, but then he’d start to pull away.  I got much more positive returns when I started being more receptive and just responding to whatever men did.   It also made me feel more confident as a woman.   Giving him the space to come to you is the most effective way.

  17. 97

    Yes, Tom10 and RW.

    Couldn’t have said it better myself.

  18. 98

    Barry, my take on the guy that chose my friend is that these things happen. He actually spoke to me earlier in the evening to say that he liked us both and wasn’t sure which of us he would be better for. I told him if he liked my friend he should go for her. I did that because I didn’t see a future with a man who wasn’t sure about me. I was a bit hurt but I’ll live.

    As for being open to men who want me that is a two way street. I am open to men who want me provided that I want them too. If I don’t find a man like that so be it. I don’t have an obligation to date someone unless I feel I have something to offer them and vice versa.

  19. 99


    I admit that I am promoting a one sided position, which would normally be untenable.
    I am forced to do so by those awkward things called facts.

    Men are attracted to the same type of women they always have been attracted to. Women’s expectations of men have changed.
    If dating relations have changed for the worse as a result, it can only be due to the gender that changed their expectations – women. That is logic.

    “If men are unable to provide what the women are looking for, it’s a two-sided problem, wouldn’t you say”

    True, both sexes must find a way to deal with the problem. Doesn’t change the fact that the problem was created only by women.

      “….and men need to improve the offering”
    Well women’s comments throughout this blog seem to reiterate this demand. But a demand is usually followed by a threat ” … or else”
    Or else you will reject us. That is indeed what you are doing.

    OK, like it or not, the ball has been thrown into men’s court.
    Are the demands reasonable ? Are they achievable ?

    Look at what women are asking for. Read this blog ! “We want men with significantly higher than average income because ….”
    Right. You want the average man to have above average income. Mmm, and the maths on that work how ?

    “No, its Ok” you say. “We are not interested in average men anyway – we deserve better than average because …”.

    So  demands  are not achievable for most men.
    Exceptions to the rule are just that.

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