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. 1

    This is so true. After reading “He’s Just Not That Into You” years ago it totally changed my perspective and I stopped second guessing what men were thinking after a first meeting because it is so obvious by their actions. Men who are interested follow up right away. Often these are unfortunately not the guys you want to hear from so lots of single women spend a lot of time and energy wondering what they can do to make the men they do like more interested in them after a date which is a waste of time and energy. A lot of women really seem to struggle to grasp that point for some reason.

  2. 2

    I struggled with this concept for a long time. I’m not sure why, but it probably had to do with low self-esteem, and the idea of having to “make” someone like me. Plus, I tend to be an “initiator”, so when I get excited about an activity, I want to share it with the person I’m dating.
    However, in Meredith’s case, why does she have drag her son along to the concert? Doesn’t she have any friends who’d be happy to go? She shouldn’t be sitting around waiting for either man to ask her out. She should have plans made, and if one of the men contacts her last-minute, then that is his loss if she is not available. When a man has been interested in me, he will either make plans at the end of the date or within 2-3 days after. You know the old rule about a man calling by Wednesday for a Saturday night date? I still follow that.
    I firmly believe that we teach others how to treat us. If I have to be the initiator, or if I accept last-minute planning, then I am further reinforcing the guy not to initiate, and not to make plans with enough advance notice. if we want a man to value us, we have to be diligent about this.

  3. 3

    I end up going to a lot of events with my brother or with a friend, not the idyllic romantic evening I often have in mind, but still. Getting a pair of ticket’s in one’s hand can be a slippery slope, you might end up initiating something simply because you have tickets, when otherwise you would let the guy take the lead. Waiting it out is always better. When a guy does initiate, you’ll have a better time because you’ll know he really wanted to go with YOU, regardless of what the tickets were for. In the meantime, a few nights out with a friend or sibling isn’t terrible, right? I have to admit that I kind of hate these rules, and here I am endorsing them, but they do tend to work with most guys most of the time.

  4. 4

    I agree with Evan wholeheartedly but also know how difficult this advice can be to follow.  Most of the women reading and posting here are educated go-getters and it can feel unnatural to suddenly have to switch to playing a more passive, receptive role.   I empathise with every woman reading this who wants to take initiative, plan and make things happen. 
    I hope the original poster will take a girlfriend, instead.  I have a number of women who’ve been supportive and fun for decades; why wouldn’t I want to share a special treat with one of them instead of with a guy who I’ve only seen once or twice? 

  5. 5

    Amen, Henriette!

  6. 6

    Whenever I’ve had this dilemma, I have to simplify or I will get caught up in my head rationalizing like crazy.  I do this by asking myself one question… Do I want to feel chosen when I am out with this guy? The honest answer is YES! That brings me back to my senses pretty quick. It’s really all about how I want to feel. When I lead, I feel insecure and uncertain…yuk!

  7. 7

    Following the simple concept of mirroring, since I read about it on Evan site, has made dating so much EASIER!!!  Sitting back and observing who’s making an effort has been an epiphany and not difficult to follow in any way. 
    Think its wise to have a zen like outlook of observation without attachment while being warm and gracious.   Thanks for another great topic!

  8. 8

    “Most of the women reading and posting here are educated go-getters and it can feel unnatural to suddenly have to switch to playing a more passive, receptive role. I empathise with every woman reading this who wants to take initiative, plan and make things happen.”

    I agree with you and also empathise with women in this situation as it’s a double standard. However, Evan’s right; it really is the only way to gauge a man’s interest. If a man is ambivalent about you, but sense’s that you really like him, he will settle into a three-month fwb situation. Sad but true.

    Perhaps you could suggest a particular activity, but only after he initiated it.

    “a few nights out with a friend or sibling isn’t terrible, right?”

    Right. I also go to events with my sister or with a friend; it’s not so bad 🙂

  9. 9

    I’m a bit of a go-getter and have had problems sitting back and letting the man lead. While I continue to struggle with it, the whole mirroring principle makes so much sense. Every time I think about picking up the phone to either call or text a guy I’ve just started to date, I have to remind myself that if he’s interested in me, he will contact me.

  10. 10

    Another conundrum solved! Thanks so much Evan.  You are “The Man”!!  Your wisdom is over the top all the time. 

    Evan, after purchasing your e-book and reading it all in one night, I have become a much sought after woman.  I have listened and used all of the advice you gave.  Everything you said works!  I finally got it.  Thank you so very much for all the advice you continue to give.

  11. 11
    Jackie Holness

    Yes, simply…”He’s Just That Not Into You.” Harsh, but true…preserve the sexy and keep it moving…

  12. 12

    Seem like if you want to go to a concert with a guy you should just ask him without the expectation of it going any further though. If he says yes he probably has at least a remote interest anyway, right? Even a night out with a man who may be a friend is funner than taking one of our children or a girlfriend who won’t pay us for the ticket. 

    1. 12.1

      Julie @12 – said
      “Even a night out with a man who may be a friend is funner than taking one of our children or a girlfriend who won’t pay us for the ticket. ”
      If you get free tickets, why would you ask a girlfriend to go with you and then ask her to cough up money for it ?  With my best GF’s we treat back and forth, don’t keep track, and always have fun. In fact, when we go for lunch or dinner together, a check grabbing fight usually ensues, with EACH of insisting on treating the other.  I usually have MORE fun out with a GF than I do with a man I have just recently met.  And I would NEVER offer my free $75 ticket to a girlfriend for a night of theater, and then demand or expect her to pay for it, but if she offers to buy me a $3 glass of wine in the lobby, I’ll accept.  Even if I have PAID for tickets, and I ask one of my GF’s, since I did the asking, and I have already bought the ticket, I don’t ask her to pay.  And I have a great time out with my girlfriends, (in some cases, more so than with a new man) No awkwardness, no wondering if I should do this or that, should have worn this or that, should or should not have said this, that and the other,  and absolutely NO PRESSURE for sex at the end of the evening ;).
      Maybe before trying to find a boyfriend, you should learn to be a better girlfriend to your girlfriends.

      1. 12.1.1

        Such a well thought out response. I completely agree. Take a man for free but expect a friend to pay for FREE tickets? That’s a crappy friend!

  13. 13

    Julie #12
    ” Even a night out with a man who may be a friend is funner than taking one of our children or a girlfriend who won’t pay us for the ticket. ”
    Why wouldn’t a girlfriend pay for the ticket? In Meredith’s case, though, the tickets were free anyway.

  14. 14

    +1! Letting him initiate is indeed one necessary (but not sufficient) way to discover his level of interest in the early stage of dating. For a while in my twenties I made the mistake of not respecting this basic advice and wasted my time and energy on a few 2-3 months flings because of it.
    @julie #12: “Seem like if you want to go to a concert with a guy you should just ask him without the expectation of it going any further though.”
    It’s at the risk of finding yourself attracted to him – or even worse, physically involved – while you still do not know his true interest level. Dating is not about making friends. Sure way to end up in fantasy land. I think it’s a much better long-term happiness investment to go to these events my byself or a true old-time friend than with a stranger.
    It’s a case of giving up the short-term gratification of the illusion of a hot date for the longer-term benefit of clarity and eventually dating effectiveness.

  15. 15

    I agree she should not ask him and should go with someone else.  And yes, as women who are expected to be go getters in every other aspect of life, in dating we must be passive and follow the man’s lead. This can be frustrating.
    I have had men complain to me that they are expected to do all the initiating, have to face rejection over and over while women just wait to be pursued.  These men said they have really appreciated it when a woman showed interest in them or made some plans or move, and it took all the pressure off of him.  They also said they liked it when a woman called them.  In fact, I know of two women with men that they pursued after the initial meeting and one is married to said man.  Yet, I think this is rare and it is indeed best to mirror the man and let him pursue. 

    1. 15.1

      I married a man that I pursued. He stopped working and allowed me to support him for ten years. He sat at home and waited for me to plan his and our social lives. He was depressed and lethargic.

      Now I vigorously screen my dating applicants with Evan’s approach, and the type and quality of man has vastly improved. I may not have remarried yet but I also haven’t locked myself into a relationship with a passive, feminine man. In essence, I am in a neutral, hopeful state.

  16. 16

    Another side to this, you don’t want to set a pattern of being the one to always initiate everything. Even in the best case scenario, if you two end up in a relationship, you don’t want to be that person. I dated an old friend of mine for a few months where we fell into that pattern. All of a sudden I found myself initiating *everything* outside of the bedroom. If I didn’t plan anything, then we didn’t go anywhere outside of the bedroom. Oh and get this: he allowed me to make plans for our weekends together.
    If the concert is really that good, and Meredith cannot find anyone to go with, I’d consider going alone. People do it all the time…

  17. 17

    I would ask out the same guy you offered tickets before and enjoy the show, since you already set the trend and wait for the other to contact you:)

  18. 18

    Meredith already asked one of the men out to a concert that she had previously paid for. That’s not necessarily a bad thing, but it is a sign of pursuit. If he likes her, he should be following up with an activity of his own, especially since symphony tickets are not cheap. But to ask him out yet another time would make her seem needy, pushy, or even desperate. Not the impression she’s going for. The other man hasn’t even gotten beyond lunch yet.

  19. 19

    Evan’s advice is spot on, as ususal.

    However, I wonder why Meredith thinks she only has the option of taking her son or one of the two guys she’s just recently met? It seems that, in the absence of either one, she’s not going to go to the concert. My advice for Meredith would be to start asking friends to go with you. It’s important for single women to have friends who can be counted on to go to social events. Otherwise, what will inevitably happen is that you’ll will end up sitting at home, feeling lonely and sad that you don’t have a date for the concert and are missing out. If all else fails, go to the concert alone!

    I speak from experience. I’ve found myself more than once in the situation where, when a relationship ended, I didn’t have anyone with whom to attend social events because I hadn’t made enough effort to maintain my friendships or to make new friends. And I was too scared to go alone. It took some time but I made new friends who I can generally rely to go to events with me. Or I just go by myself. I’m a very self conscious person and, while at first it was terribly awkward to go to a concert alone, it didn’t take long before I got over myself and learned how to make conversation with people I didn’t know. In fact, I’ve made a number of good friends that way and even a few dates. The bonus is that once you are confident enough and have a strong enough social circle to not need a date to an event, it becomes much easier to stick to mirroring.


  20. 20

    A guy’s perspective – Yes, I enjoy the chase.  Yes mirroring works.  That being said, there are a few things to keep in mind.
    1.  When you mirror, show some enthusiasm and passion.   When a woman responds 36 hours later with a 5 word text it is difficult to feel that she is showing anything but one step above indifference.
    2.  Men do have to take the initiative – just remember that men face rejection day after day.  If you are interested, drop some not so subtle hints.
    3.  Women and men think differently – guys aren’t so good at reading between the lines.  Show your interest without scaring him away but don’t be so forward that you scare him away.

    I realize that all three tips say basically the same thing – I’m lucky that  I can date a different woman every night if I so choose – If I’m left guessing whether she is interested i have one response — “next”

    BTW – nothing ventured, nothing gained — if the OP doesn’t make a move on one of these guys, I’m going to assume that  she will never see them again.  If she asks one of them out, she won’t be in a worse position than she is in now.  Maybe she’ll find one of them is a great guy and friend for life or maybe he’ll discover she is a wonderful woman.  There is an exception to every rule….

    1. 20.1

      Hmm… “next”- sounds defensive. What if she isn’t sure at once whether she is interested? Sounds to me you might miss out on a great girl just because she isn’t all over you at once… and like uncertainty is very uncomfortable for you 😉 shouldn’t it rather be exciting..?

  21. 21
    lux aeterna

    I was just about to message a man tonight when I decided to swing by this blog again. Thanks, that stopped my message! Maybe one of the men will call and ask  Meredith out on Saturday, and she can then mention, by the way, I have some tickets…

    Years ago, I had just been dumped right before going to see the Welsh National Opera that I had bought the tickets for. Furious and date-less I decided to bring a male friend instead. However, the three guys I asked were all busy that night, but not for the whole night. So… guy number one came with me for the first act, guy number two for the second act, and guy number three got off the train just in time to rush inside and catch the third act. The couple sitting next to me gave me some confused looks. And this was all before mobile phones – we were good at logistics back then!

    1. 21.1

      Perfectly managed! 😀

  22. 22
    Mr. R

    This advice does have the ring of the book “He’s Just Not That Into You”, as a side note.
    Because really – he’s just not that into you if he’s not calling you. Evan takes it a step further with the mirroring (which works, by the way).

  23. 23

    I have to say that while I don’t agree with 100 percent mirroring or letting the guy do ALL the work, I still don’t tend to make moves until we’ve been out at least five times, and even then only 20ish percent of the time. It’s totally fine to call a guy once in awhile, and I wouldn’t feel comfortable with a man who was put off by that. Also, I do invite men to things all the time, but only if I’m not truly interested in them for a relationship and/or see them as more of a friend.

    I do think women would miss out on a lot of opportunities in life by 100 percent mirroring – I take it more as the overall effort/enthusiasm you show for a man rather than literally keeping score of every initiation of contact – but it depends on the stage of life you’re in and what you’re looking for. I’ve certainly made good friends out of dating, but I can understand those who are at a stage where they are much more singularly focused on marriage may not want to bother with that. The key for me has been to regularly go on dates with people from real life as well as online, not sleep with anyone until there’s a relationship, and just generally be more social and invite people to more things in my non-dating life. If someone doesn’t respond or call, I have plenty of other dates lined up and other social activities and it doesn’t hugely matter. If this woman can’t think of other fun friends to invite, maybe she should start there.

  24. 24

    I was in this exact same situation two years ago. I had great tickets to
    a baseball game and had recently been out with two guys, both of whom I asked to the game. Guy #1, seemed really into me (and also really into himself) and we had been out on three dates. So, I thought, what the hell, I’ll just ask him to go to the game. He declined my invitation and I didn’t really hear from him much after that.

    I asked Guy #2 and he accepted my invitation. It was our second date, We had amazing seats to the game and had a blast together. EWe dated through the summer, but ultimately our romantic relationship ended. However, we are now friends and occassionally go to a show or go skiing together….

    I agree with Evan to a point, but there is no point in overthinking how to use concert tickets. I read “He’s Just Not that Into You” and also Read Evan’s Ebook and Blog. In the end, I decided that if a guy needs me to play games, then he’s probably not the guy for me. I have been dating the same guy for almost a year and didn’t have to follow a set of rules to atttract his attention.

    I say ask the guys to the concert and have fun with it. 

  25. 25

    If she’s not that concerned about whether or not a relationship will develop with one of these guys–and she might not be–then she should feel free to invite one to the concert. She might invite the one she’s less interested in. But I totally agree with some of the other comments; why does she not have a girlfriend to ask? Do your own thang, sugar, and don’t worry about the boys. They’ll show up if they’re interested, and if they’re not, they won’t. In the meantime, you could be saving your energy and looking forward to a fun show with a fun friend.

  26. 26

    Great answer, wholeheartedly agree, and so many people will argue with this, it’s silly.  #8, Tom10, right on!  Had a very protracted on line conversation on a forum where a young man and women were arguing against the advice of two more mature, seasoned women were giving another woman–our advice:  DON’T initiate contact after meeting a man for the first time–how hard is that?  You’ll never know how interested he is.  Needless to say, she disregarded the good advice, and contacted him.  He was ambivalent, then texted for a booty call later that week…sigghhhh….

    A female ‘go getter’ is working out of her masculine energy, nothing wrong with that in work situations, furthering a career or getting a project or errands done.  Masculine energy doesn’t excite a man.  Being receptive and leaning back is not negative or weak, it’s being in our feminine energy, recognizing we are the ‘prize’.  It’s coming from a place of power since men can’t fully be in female energy, it’s a mystery to them.  Once a woman can really get this change in attitude, she will master dating and men.

  27. 27

    @Toni #24: “In the end, I decided that if a guy needs me to play games, then he’s probably not the guy for me.”
    I agree about not “playing games”. However I do not see mirroring in the early stage of dating as playing games. Refraining one’s enthusiasm is no more game playing than – for example – refraining one’s tendency to blurt things out without thinking. Self-control is truly necessary in the building and nurturing of a healthy relationship. Why not starting early?
    Now, I think that mirroring only makes sense in the very early stage of dating, and it needs to be accompanied of very clear demontrations of appreciation for his efforts and some form of reciprocation by contributing to part of the expenses for example. If I were a man, I would also need confirmation of her interest and  would not enjoy taking a woman out several times while still wondering if she is truly interested or just using me to alleviate her boredom. Therefore, as a woman, after a few dates (number depending on how things started and developed), I think it’s time to start proposing dates as well, and then maybe at a pace of 1 out of 3?
    That’s what I did with my boyfriend, without knowing it was called “mirroring” : ). At that time I had not discovered Evan’s amazing blog… Anyway, I let my man make plans for the few first dates, and each time expressed my interest, appreciation, and excitement. At the third date, which was still his plan, I chose the restaurant for lunch and picked up the check. That was a nice transition towards participating more, and later on, maybe for date #8 or so I suggested my own idea. I would have prefered starting initiating earlier but he always made plans before I could even have time to do so! Therefore initiating might happen earlier or later depending on individual circumstances, but I would never have asked him for a date before date #5. On the other hand, I offered to contribute financially as soon as date #1 (which was refused until date #3 : ).
    As I was involving myself progressively more into the dating process, I asked him whether he appreciated it or would prefer to keep 100% of the lead. He explained that he really liked taking care of our first few dates, but loved it when I started asking him out later on.

  28. 28

    Goldie #16 “Another side to this, you don’t want to set a pattern of being the one to always initiate everything.” This is exactly why I resist this sense that men should lead all, or most of the time. Because it can easily slip into that being the pattern – and/or the expectation. I do believe that amongst younger folks, there’s less of this rigidness around gender roles, and how attraction is expressed. But since Evan always comes in with comments about being practical right now, I’ll move on to my own experience.
    Enthusiastic response is great in the beginning, and mirroring as such is fine in my view. However, in my book, it’s value drops greatly over time, if that’s all or mostly what a woman is offering. If I am doing all or most of the initiating past date three, I begin to seriously question her level of interest. Such situations have never worked out for me in the past. And everyone I have dated for significant periods of time has moved fairly quickly (within a handful of dates) into sharing the role of initiating – making phone calls, coming up with date plans, paying for part or all of dates, etc.
    If you all wish to dismiss what I have to say as “an exception,” that’s fine. But I don’t think – in the case of Meredith – a single invite to a concert is a make or break deal. If it’s the pattern, then I’d agree the guys in question are probably not into her.
    Here’s one more point to consider. Being ambivalent can mean many things early on. Because YOU DON’T KNOW EACH OTHER. I have felt sexually attracted to women I wasn’t sure about dating in the long run. That instant chemistry thing that often flames out after a few months. Been through that plenty of times. And I’ve also felt unsure about the sexual attraction with women who I otherwise really liked. There was some attraction, but in the case of one women I ended up dating for three and half years, the attraction took time to build up.
    Point being, you can weed out a certain percentage of people as “not interested” early on, but with the rest, whatever is there often won’t be clear for months. Until you actually know each other better.

  29. 29

    My understanding is that you mirror until a guy expresses his interest in being your boyfriend in an exclusive relationship if thats what you want. I don’t consider showing a guy that you are open warm appreciative and receptive but don’t pursue men to be “playing games”. 

    If you are a female with lots of masculine energy and you are pursing a guy with more female energy then I think its OK to initiate things but that is a less common situation and you can expect to play the male role in that relationship.

    I have noticed an interesting result of this though  Ive met a few men out and about. They keep contacting me every few days, I just mirror and yet they haven’t asked me out yet over the last few weeks. Obviously they have something else going on and since they haven’t initiated meeting then it probably time for me to disappear

  30. 30

    I am pretty good at not asking them out anywhere, and letting them plan and pursue me. It even feels better when this is done. However, the random cute texts I have to stop. I have deleted a few numbers so I am not tempted between waiting for them to call. 🙂 

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