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. 121
    Karl R

    You’re describing the world that you think “should” happen. You’re describing what you think is “fair”.   It’s a nice sentiment, but it’s utterly useless for dating.
    If you want to succeed in dating, you need to know about the way the world is, not the way it should be. You need to know the strategies that work, not the ones that are fair. You’re trying to make the world conform to your wishes. That’s a recipe for frustration.
    If you want to do 50% (or more) of the pursuing, you need to identify the men that strategy will work on. Generally, they are the men who are shy, socially awkward and lack confidence.

  2. 122

    Another aspect of asking a man out because you happen to get free tickets is this:   Not only are you appearing to be the “chaser”,   it also appears that you have no friends.     I get comp tickets to live theater quite a few times a year.   I ask my close girlfriends first.   If they can’t make it, I go to my FB page, and I have a sub group of my acting/theater friends (none of whom I have an interest in dating) and I put an announcement out to my actor friends saying that I have an extra comp ticket to whatever theatrical event — first one to respond, gets the ticket.   Since tickets to this theater generally start at $50 and are typically $75,   I have no problem getting one of my fellow acting friends to go.   Even if we aren’t particularly close friends, we end up having an enjoyable evening, and the other friend will usually buy me a glass of wine and pick up the parking tab.   So   I would NOT ask out a man whom I was in the beginning stages of getting to know,     with my comp tickets.   I don’t chase men, the other reason being is I don’t want him to think , “Boy, she must not have ANY girlfriends, I wonder why ? ”
    Now, I usually also have a wallet full of movie passes, StarBucks gift cards, etc. that I get from work, and if a guy I’ve been out with a few times asks ME to the movies, I will casually mention that I have a have a pair of movie passes that I won at work and offer them.   Or if we are at one of the free concerts at the mall   I’ll   might say “Oooh, let’s go get a latte at Barnes & Noble, I still have the gift card I won at work that I need to use”.     But unless I was in a flourishing, well established relationship, I would not use my comp tickets, movie passes or gift cards as an excuse to ask a guy out.   Asking out is HIS job, saying yes, is MY job.
    The only exception I make

  3. 123

    Hi Evan, new to your blog but it is great as i am newly single (within 2 years) and do not have alot of dating experience (was married for 15 yrs and it was to my first LTR… lol – oh gosh the mistakes i will make now with such little experience….).   I do like the concept of mirroring, because it is a thrill when a guy is pursuing, although does it have to be strict is my question. Like the poster in this article – i don’t find myself thinking its a big thing to ask a guy out.   I have in the past and I ended up dating someone i probably would not have, had i not asked them out.   To me the relationship that occurs after you ask someone out is going to be a hit or miss on your personalities more so than who asked who out first.   Or even who initiated more contact.   I agree that you will find out very soon his level of interest if after the first date he doesn’t contact you more than he did before the first date – and so right now, i guess that would be my question   – i sent a message to a guy online – we started talking, exchanged numbers, he texted a few times first, then i did and i asked him to meet up on the day i was free.   So basically i asked him to meet first, but this is a first meeting and to me, its going to be what happens AFTER a first meeting that will be a tell tale sign if i should move on or if it we will hit it off.   Basically he couldn’t meet the day i offered and then he counter-offered this coming weekend.   I agreed.   So, do you think its a big deal who sets up that first meeting   – i kind of feel like i don’t mind initiating some contact or even asking out to get a first meeting out of it, but after the first meeting, if the guy doesn’t show the same level of interest or pursue me or contact me, then i would move on.   My thoughts to the Meredith? I would totally ask one of the guys – because if they are really interested in her, she’s going to find that out with how they respond – and i don’t think that if they are interested, that their interest will wane by   NOT spending some time with them.   I think the mirroring is a guide to woman to say, do not chase – which to mean does not equate to never initiate or ask out – it just means if don’t keep initiating or ask out again if they don’t do the same in return.  

  4. 124

    Im sold on mirroring but Im interested in feedback from other women , who agree that this is very effective, on how they manage guys who complain I dont initiate anything.   The guys that complain are usually ones Ive been on a couple of dates with.   I guess they are used to women pursuing them .

  5. 125

    This is an awesome article!   I just met a man online a couple of weeks ago and was stressing about whether I should be texting him etc.   I decided (after having a stomach ache for a couple of days…lol) that I would sit back and let him contact me.    He did!!   Great advice Evan.   Thanks.

  6. 126

    I think the woman who wouldn’t ask this question and could care less and just ask the guy is usually the woman the guy would end up being interested in regardless of who asked. Whereas, the woman who would ask this is already in the grey zone and feeling less confident so her asking the guy would probably never work for her.

    As for myself I would ask the guy to accompany me if I wasn’t that attracted to him, because then I am more confident and could care less what became of it, probably my aloofness in that scenario would drive the guy closer to me even though I did ask him….lol

  7. 127

    Not sure how long ago it was posted but I read all comments which I rarely do.

    I liked the concept of mirroring, it sounds fair to me. I am in my late 20s, I run small business and moved out of my parents’ home to another country to try myself out and see what I worth. I have to say that in all aspects I have either succeeded or getting there…. in all but one… Needless to elaborate…

    I met this guy on a dating app and we texted for a month. We were both travelling, then he broke his leg but after one month we still managed to meet. He came on crutches which I of course appreciated (and told him). I thought the date went amazingly well. We spent 5 hours chatting about everything…

    Well, it’s been 4 days since then and neither of us messaged. Some of my GFs tell me that we live in 21st century and that I need to initiate the contact. But frankly speaking, I have been doing it for all my life. Nothing good ever happened out of this. Yes, I dated two guys for more than a year each but in the end of the day, we broke up and I realised that they just not the right guys for me. I could never understand why I chased them and made them fall in love with me on a first place. But that’s another story.

    With this guy, I can see what went wrong – I got attached during this one month of texting. I couldn’t eat or sleep, so much I was looking forward to the date. And, then, when we finally met and it went great I was so sure that he would be in touch that when he didn’t message me I felt very hurt, and unfair and kept (still keep on) questioning what went wrong and if it was my mistake.

    I had this huge desire to message him finding all sorts of excuses why he hasn’t texted me yet but then I realised that no matter what happened from his end, I won’t feel comfortable taking the lead (running business is more than enough).  I thought that maybe his leg hurt (he was in cast and had a surgery week before the date – read between the lines: how eager he was to meet with me offline). I also thought that maybe I was too needy or showed too much interest and that’s why he hasn’t texted. I also had this idea that I didn’t show much interest and saw no point in getting in touch (Although I gave him a kiss on a cheek and gave compliments, he just hugged me though, but complimented).

    So basically after I ran out of this list of possible excuses I came to a very painful conclusion: HE IS JUST NOT THAT INTO ME. I am sure you would agree, it is one of the most difficult statements one can ever say to oneself… especially if you really liked the person. So now, I am trying to stick to this thought that I will not chase the guy. I will do nothing for a change. And, as cheesy as it may sound, if he is the One, then he will find a way to show it to me. I just don’t want to take the lead again as I simply believe that I deserve much better. Just wanted to share my story. I am sure many of you will find it very familiar.

    P.S. Sorry for my English. It’s not my native language. Peace!

  8. 128

    One of those go getters here.   Initiator, aggressor, take charge persononality, leader, in a male dominated profession and too busy to play games.   I don’t think either person should be the primary initiator all the time.   I’ve never had any issue getting dates but long term relationships since I’ve been in my chosen   profession have evaded me beyond a year or two.   I’ve tried to follow this advice but it’s not me.   I was pretending   and unhappy it was forced.   I don’t want to pretend to be someone I am not.    I think relationships from the start should be equal effort and interest.   While I recognize that some men don’t respond to that and that may leave me single I’m okay with that.   I’ve grown very tired of trying to contort myself into some other person to make men not feel intimidated or more masculine around me.   I don’t expect them to change.   Pretending is too exhausting.   I’m not saying Evans advice is not correct and useful it’s just not something I can do.

  9. 129

    It’s funny how you don’t really get something until you experience it yourself in reverse. This guy took it way further than I ever would, but it was a good learning experience for what not to do and how making excuses for not-interested behaviour, or finding reasons to continue to text someone who’s not into you, or ambivalent, or weighing up options, is dangerous.

    We had some nice initial banter online for the first few messages, then this guy (let’s call him Bob) did the following:

    1. Overshared about a medical thing waaayy too soon

    2. Texted three more times in a row without me responding

    3. When I didn’t respond, gave me his number

    4. When I didn’t respond to that, asked me out for the weekend

    5. (I would usually block at this point, but following the Golden Rule – thanks Evan!) I wrote a  very polite message letting him down easily

    6. He still didn’t get it and again asked me what I was up to on the weekend…etc etc and then got a bit childish and negative when I again politely declined..

    There’s more to it, but the point is that Bob’s neediness and not understanding subtle signals and being too eager COMPLETELY destroyed my attraction to him. He was one of a few guys I was interacting with, and clearly there was enough for me to engage with him at first, but  this behaviour ruled him out entirely and I now feel quite repelled.

    I’m sure, to a lesser extent, I’ve taken myself out of the ‘running’ by being too communicative and following up once too often. If you don’t follow up and let things develop more organically, you’re more likely to either increase your attractiveness by not being needy, or find out early on that he’s not that into you, but without completely turning him off.

    This is where mirroring is useful. It’s probably most useful for overthinkers (like me) and to people who are attracted to alpha males (like me). I have to play it carefully as like some of the other posters, I’m not dealing with American males (I wish I was!), so not to the letter of the law, but I definitely try to follow the spirit! 🙂

  10. 130

    another point missed- you bought 2 tickets but didn’t have someone in mind to take when you bought them? I would’ve had a friend agree to go with me or just bought one and gone solo. Learn To go on dates with yourself, doing the things you love, without needing a date. It’s really liberating and fun!

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