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.

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