What You Should Be Talking About On the First Date

young adult couple dining out in a restaurant

Have you ever been nervous about a first date?

Not because you’re insecure that he’s going to like you; you’re actually quite confident that most men will respond to you.

The nervousness I’m referring to comes wanting to know what happens AFTER the first date. Your questions buzz through your head.

Is he financially stable?

Is he close with his family? Is he emotionally available?

Is he in a place where he wants a long-term relationship?

Is he going to call me tomorrow to say he wants to see me again?

In other words, you want to know the future — and protect yourself from heartbreak by figuring it out as soon as possible.

I don’t blame you. The problem is that even HE doesn’t know the future.

Let me share a story with you. I got a new private client the other day. Early 40’s, bright, successful, and really excited about coaching and learning about the opposite sex. This woman is not just an avid dater — she’s a learning-about-men MACHINE. (I love women like this, by the way.)

As she peppered me with questions, it was clear to me that she had done a lot of research. It was also clear that she had her ideas formed by what she had read previously.

This is dangerous.

You know what a first date is for? It’s for FUN.

Because while there’s a lot of good stuff out there, no one expert has all the answers. When you start believing that one person (including me) has the gospel, you cease being a critical thinker. I read a lot, but I always draw my own conclusions and judge whether it’s effective in the real world. I would encourage you to do so as well.

Here’s a perfect example of advice that sounds good in theory, but doesn’t hold up in practice:

Two prominent relationship experts — both 50-year-old women who haven’t dated in 20 years – advise women to tell men what they’re looking for on a first date.

They suggest that if you’re serious about marriage and children, you should put that on the table from the get-go on Date 1. The theory is that you don’t want to waste time — yours or his — and if your “honesty” frightens him off, he’s not the right guy for you.

This is WRONG. Dead wrong. Like, it’s so wrong, that I can’t even fathom that my esteemed, well-intentioned colleagues would pass this off as valid advice to unsuspecting women who trust them with their lives.

Here’s why:

In being “honest”, you’re sabotaging the dating process and making the man NOT want to get to know you better.

Not because you want to get married and have kids — he does, too! — but because you sound needy and desperate and tone-deaf to the normal conventions of first dates.

You know what a first date is for? It’s for FUN. It’s for you to get a better sense of me and whether I’m a solid catch, it’s for me to determine if we’ve got some attraction and easy conversation — and it’s for both of us to determine whether there’s enough potential to meet for a second date. That’s all.

When you introduce concepts like marriage, kids, religion, politics, money — trying to ensure that the person across from you is a good long-term prospect, you essentially turn from a pleasant, fun, likeable person …into The Interrogator.

Men don’t like the Interrogator.

Doesn’t matter if The Interrogator is smart, hot, and interesting. If a man gets the sense that you’re testing him for earning potential, or fathering potential, or husband potential, he’s not going to feel comfortable.

Men don’t like the Interrogator.

Because suddenly he’s not the guy who’s buying your drinks and trying to make you laugh — he’s being interviewed like an intern who is applying for a lifetime job at your company. Believe me, that doesn’t make him like you more.

And if you want to get a second date, it’s kind of important for him to like you!

Which is why it’s my job to tell you to ignore this kind of well-intentioned advice. It may sound great in theory, but in practice, it falls apart.

Let me show you how.

First: Imagine you had a boyfriend you LOVED. And he told you after 8 months together that he was taking Zoloft to keep his mood up. Would you dump him? I sure hope not.

Now imagine that he told you that on the first date. Does he get a second date? I’d be surprised if he did.

There are things that we’re willing to hear LATER in the dating process — once the ice has been broken, the foundation has been laid, and the relationship is strong.

And your desire for marriage, family, and the ability to potentially be a stay-at-home mom is something that you’re better off springing once he already LIKES you and has something invested in you — not right after he learns what you do for a living.

To suggest otherwise — to encourage you to “save time” by offering your innermost desires on Date 1 — is simply irresponsible and ineffective.

For every bad man you scare away because he’s not ready for a relationship, you also scare away a good one who IS ready, but wants to date a well-adjusted woman who knows better than to get so heavy on a first date.

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  1. 1

    I think the well-intentioned but incorrect advise of laying all your cards on the table early is put forth in the interests of “not wasting time.” While I can understand not wanting to invest months in someone who is not a good long-term prospect, attempting to screen them this early is counter-productive.
    As you say, a first date should be FUN. I went on a lot of first dates during my online dating days, and I can safely say that none of them were a waste of time. Most didn’t lead to a second date, but I still had a good time getting out and getting to know an attractive guy. Even the one time the date was not good, it still made for an interesting story.
    I think too many women (and some men) are so fixated on their final “goal” of finding a long-term partner that they forget to enjoy the journey.

    1. 1.1

      what a GREAT advice! enjoy the journey and dont focus on the end result! LOVE IT! thank you!

  2. 2

    I’ve used this approach in my dating this year – it appealed to me just because I’m generally positive and fun, and at the same time pretty selective. I figured, since the odds of me liking a guy enough to want a second date are fairly low, so why don’t I just make sure both of us have a good time. I have two teenage sons, most of my friends throughout my life have been male, so I’m “one of the guys” and get them pretty well. So, for a first date, I show up with a huge smile on my face, I laugh at his funny stories, I listen attentively to his tales of woe. I make him laugh – a lot, in fact (guys really like my sense of humor). Every single time when the check comes, I reach for my wallet. And, if needed, I open it and pay for a drink or my half or whatever. I mirror whatever degree of physical contact he wants to maintain when we say good-bye. Everyone leaves happy, no one’s time is wasted.
    Sounds good, right? Well guess what, this approach seems to work very well on guys that you can’t pay me enough to go on a second date with. Safe, needy, clingy, boring guys. The ones I like – the smart, funny and confident ones? Well I guess it sort of worked on one of them (we went out for another month and then both agreed it wasn’t working well enough for us to get into a deeper relationship). Two disappeared without a trace – never heard from them again after the first date. Another one really liked me and wanted to come back for more (and was very sweet about it), but he was from out of town and it had been a “no-pressure dinner” to begin with. Last one I went out with that I liked, texted back saying there was no spark, then came back for two more amazing dates (amazing for me, anyway…), then said “um, no, still no spark” and left for good, which hit me pretty hard. Still recovering from that one.
    So, two weeks ago, after this last guy walked out on me, I figured I’d bite the bullet and buy Why He Disappeared, to find out why the kind of guy I attract with my first-date behavior is the opposite of what I want to attract, and also the opposite of what I know from experience that I would have a good relationship with (I’ve dated enough RL friends to know what works and what doesn’t). It turned out to be a really good read, thank you Evan 🙂 and my take-away from it so far has been that, on first dates, I might be concentrating too much on making sure that the guy has fun. I put up a whole standup act, I meet at a place convenient to him, I offer all kinds of help… don’t get me wrong he has a good time. By the time he walks away, he’s been entertained, he’s been pampered, he’s got my leftover dinner in a box to take home with him so he won’t have to cook the next day… But he cannot really tell whether he has shown me a good time or not. I was too busy taking care of him to really show my appreciation for what he did for me on that date.
    So, last weekend, for my first date with a really cool guy I’d met shortly before, I decided to switch gears, listen more, and entertain less. I also warned him of this flaw that I have, and said that I do this unintentionally and with the guy’s best interests in mind. And then I tried really hard not to do it. Well it’s too early to tell, but so far, the man is sticking around, following up daily, making future plans and doing all the things no one has ever done for me in my short dating history (a little over a year). Time will tell 🙂

  3. 3

    I personally would never bring up that I want to get married on a first date; I might want to get married – but not necessarily to HIM.     I have had guys ask me on a first date what I want: and I say “if the right guy comes along, I would consider it though.”  

    I have been on dates where I have felt that I am being sized up as potential wife/mother to his kid/etc.    It is disconcerting.  

    Goldie – can I ask how you meet people?   Are you on match?

  4. 4

    Evan, your example is really interesting to me because variations of it have been coming up on other dating sites recently. I have to say as a man who has been serious about finding a long term, committed relationship – I’m kind of torn about the disclosure issue.
    When it comes to online dating, it seems very valid to me to spell out some of your long term relationship goals – if you have them – right in the profile. Theoretically, this would help weed out those looking for something casual before you actually meet them. (It doesn’t always work obviously, but I think making it clear that you’re looking for marriage and children in the long term is really helpful, and a good filter as well.)  
    On the opposite end, I wrote a post recently detailing an experience I had with a woman who popped an “I want babies now” statement on me on date number two. It felt beyond rushed, and certainly scared me away from pursuing a relationship with her.
    So, I think there needs to be some kind of balance between having fun and enjoying yourself on first dates, and doing some sussing out of what the other person wants and where they see themselves heading in life. At least in general.

  5. 5

    I don’t understand why telling a guy that your hope is to marry and have children makes a woman appear desperate and needy. Also, I don’t think saying that AND having fun are mutually exclusive. Isn’t part of deciding if you are a good catch is seeing if we want the same thing. If he wants a FWB and I want marriage, I really do want to know that sooner rather than later. And the men I have dated have often been very honest about what they want on the first date. If they don’t want what I do, I move on. I really don’t understand why that’s bad.

    I am not certain it is fair to criticize your colleagues for not dating as you yourself have been off the market for quite a few years. I suspect if they were 50 and single then they’d be criticized for that as well.

  6. 6

    Congrats, Goldie!
    I’m glad you are finding the difference between being fun and enjoying yourself and entertaining others so completely you lose yourself….
    I always used to entertain my dates. And they all used to call me back! But I wasn’t really being myself. Also, I found that my trying to be superfun and super-easy was a different way of exerting control over the situation.
    I think the key that Evan is pointing out is to relax and be receptive and easygoing to have a good time. In my (soon-to-be married) experience, guys like when you are nice, open and receptive to them and mostly, they want to see that they can make you happy.
    That said, it is really, really hard to go out on dates and not know where things are going. But if you *don’t* overly entertain, and are just receptive, it’s less disappointing.

  7. 7
    Evan Marc Katz

    Kenley, telling a guy on the first date that you hope to get married is INEFFECTIVE because it’s tone-deaf to normal first date behavior. It’s not that the intention is wrong; it’s the execution that leaves a lot to be desired. I can’t tell you how many women clients have told me how creeped out they are when a guy instantly starts talking about marriage. It works both way, folks.

    And I’m not criticizing my esteemed colleagues BECAUSE they’re married. I’m married, too. I’m criticizing them because I fear they’ve been out of the market for so long that they’ve forgotten how real people react in real situations. Some advice makes sense in theory, but falls down in practice. This is one of those times.


    1. 7.1

      I agree with you, Evan. Last night I went out on a first date with a seemingly nice guy, and he asked me three times if I wanted children. He also told me about his medical history and the sort of meds he takes. TMI. And the questioning about me wanting children or not was annoying. I will not go out with him for a second date.  

    2. 7.2

      I agree with Evan Marc Katz as I had the same experiences from both side. I myself  as a woman don’t like to mention that I want marriage on the first date. But, I decided to listen to some women relationship counsellors and I brought that up in the chat I do and on the first date with men. I felt needy and desperate   within me and it was not a right felling for me either… Although, the guy I dated still wanted to see me for a while, but I could observe myself how controlling I am on him to make sure he is the one as I only date men for marriage… Instead I could date other men at the same time and select which one is the right man for me based on what I really want and be a lady :). feminine, fun and secure …..

      Also, once I dated a gentleman a few years ago who from the first date he was telling and pushing me that he wants long term relationship. then week after he told he wants kid too in a year and half.. then he asked me to move in together…All, in a month or so??? Honestly, it was scary and I judged him as an insecure and needy man and I said NO… a big NO… then he started judging me back that I would not be a right person for him and not a good mother for our kids :))). so, what happened ? he lost me. Although, if he was letting the dating process goes smoothly and properly and I would feel comfortable around him. I was sure he was the one :). But he went too far….


  8. 8

    @ adk #6:
    “Also, I found that my trying to be superfun and super-easy was a different way of exerting control over the situation.”
    Yes, this is my impression too. This would definitely explain why, after dates like this, I’d have to chase the omegas off with a stick, while the alphas would never call back. The latter do not like losing control, while the former don’t really care and may even prefer it that way 😉 Too bad I didn’t buy the book sooner, wouldn’t have lost some really cool guys if I’d only parted with my $27 a few months ago rather than just now 🙁

  9. 9

    I’ve had first dates where the topic of marriage and children comes up in conversation. We may be talking about where we are from, where we went to college,   how we came to live where we do now, where (if anywhere) we see ourselves moving, do we want marriage and kids to be a part of the picture, etc.
    I’m curious, if it comes up in the flow of conversation (or he outright asks), does that change your take on things?

    1. 9.1
      Evan Marc Katz

      There’s nothing wrong with admitting, in context, that you want to be married. It would be odd NOT to deal with that in a very easygoing, matter of fact fashion.

      However, that’s a VERY different thing than asking certain questions to evoke certain answers from men regarding THEIR take on marriage. If someone seems to PUSH the marriage card on the first date – man OR woman – it’s pretty bad dating etiquette.

      1. 9.1.1

        That is very true Evan I have just realised I dumped a very good girl about ten years ago because if her comments about marriage on the second date, she must have thought I just wanted sex because she made the “sex only after marriage” comment, and I got scared off, I took it on two options: either she saw me as shallow guy and wanted to “fish” me with sex, or she was desperate…

  10. 10

    I’ve got to ask this, though – when is it OK to ask the other person what they’re looking for, as an end goal of their dating? Happened to me twice this year that I assumed he was looking for an LTR, because I was, while he assumed I was looking for casual, because he was. I agree, first date may be too soon for this type of questions, but finding this out after four or five dates can be a tad harsh for both sides. When’s the right time? FTR, the person I’m seeing(?) right now brought this topic up himself right away, so we both know where the other one stands – but that’s a pretty rare occurrence in my experience.

  11. 11

    I got ya. Thanks for answering Evan!

  12. 12


    I’m a firm believer in making intentions clear from the outset but I think the difference is in how you make them known.   To me, first dates are for gauging your interest in a  person…as a person.   Not as a potential husband, potential father or potential something else.   From personal experience, I can say that I have been uncomfortable with men who have been highly emotional on the first date and given me their life histories along with future plans which include…you guessed it….babies.   These situations do not typically yield a second date for the men in question 😛
    On the other hand, I appreciate a quiet statement about future plans or expectations when made in context.   If the topic comes up naturally, as it sometimes will during the course of a conversation, it makes sense to state that you are in the market for something long term with the right person.   If it doesn’t, there is always the second date or the third.

  13. 13


    Wonderful observation about alphas and omegas.   I’m running past experiences against this and you’re spot-on!   The true  omegas liked being taken care of and admired my independent woman aura.   While  this  behaviour  came very naturally to me, I subconciously relegated  my date  to the “little brother” pile.   I successfully annoyed the alphas or pseudo alphas and they disappeared.

    Luckily  for me, my current  hottie is a happy balance of sweaty man and mushball.   He lets me wear my man pants sometimes and I’ve learned to allow myself to just be taken care of on other occasions.

  14. 14

    @Golde #8
    So, you only date the A’s and the Z’s?   Only the guys at the top of the social hierarchy or at the very bottom?   What about all of those nice beta and gamma guys?

  15. 15

    @ Kenley #5:

    Telling a guy you want to get married and have babies on the first date, i.e. basically the first time you’ve met him, is akin to telling him,  “I want to get married and have  babies now!”   Whereas if you  mention that to him on a subsequent date (later is better, and as casually as possible is best), you’re telling him, “Yes, I want to get married and have babies, but it’s not first and foremost on my mind, and not something I need [from you] right away.”   (The “from you” is what he will be thinking, even though you may not be interested in him being your husband and father of your children.)

  16. 16

    In my online dating profile I made it very clear that I was looking for a LTR that would lead to marriage if a love match happened. Did the men I meet feel the same way? NO! They looked at my picture and hardly looked at my profile. I read all the men’s profiles that I met carefully. I did not meet any man who was looking for FWB. So, how do you know what someone is looking for if they don’t say what they want in their profile? Can you ask them a question online before you meet them? I suppose asking what they liked about my profile might at least help me know that they read my profile.

  17. 17

    I never bring up marriage first with a man. Not on the first date or any. I think men are hard-wired to assume that most (if not all) women want a relationship and  soon following  marriage. Men are use to hearing, “so where is this going?” And I think, women tend to want to strike a deal first (commit the relationship)  to make sure they are not wasting their time, and know that they are headed for marriage if that is what they want.

    So when a budding relationship begins,I say nothing. I never talk exclusivity until they  do. I always let them assume I’m dating others even if I’m not. I never mention marriage or my long term plans.    I think this is not what men are use to…..and then they want to figure ME out.

    Without fail,  the men that I’ve had relationships with, always brought up exclusivity first, and within 6 weks. They have also been the first ones to ask me (knowing that I’m divorced) “Would you ever get married again?”, or “Do you  want to be married again?”

    I absolutely want marriage but I say, “Well, I’m certainly not jaded by my divorce or anything, so if the right man, and the right situation presented itself, I’d  be open to it.”   Then I can naturally turn the question back on them, “Why do you ask? Do you want to be married some day?” I get my answer, they brought it up, and it doesn’t appear to be my top priority.

    The relationship seems to pick up after that  and I think it’s because they feel no pressure from me or feel like I’m a desperate woman looking to lock  them down  asap.   If anything, they  act like they have to lock  ME down because I maintain  a little aloofness toward the whole subject.  

    A little coquette goes a long way, imo.

  18. 18
    Kat Wilder

    Talking marriage – or divorce – on the first date? Not in concrete terms (“I always thought I’d get married by my xx birthday), but maybe in vague general terms – “I would like to get married one day when the right person comes along” or “I still believe in marriage, especially if people want to have kids.”
    If you meet online and your profile says you’re interested in a LTR and don’t object to kids, well, then your date knows (if he/she is paying attention) what you want and vice-versa. (Although, as SJZ points out, some people don’t read the profiles; you are totally right in asking what they liked about your profile. If they can’t remember it or can’t find one thing to mention, then that may be a flag.
    As Evan says, first dates should be fun, and should help you know more about each other in genuine ways – not a set of rigid questions you ask each and every person. People respond to people who listen and ask intelligent questions that prove they’ve paying attention to who they are as individuals. And, there should be flirting!
    If you go into a first date without a lot (I’d actually say no) expectations, you are much more open to having a genuine connection with someone (or quickly finding out you have no connection!)

  19. 19


    That was really perceptive ADK. It is another form of control. Never heard it said like that, but if you aren’t being yourself, and trying to be the “cool” chick, you are doing it to manipulate and control the situation.

    Well said 🙂

  20. 20

    In recent months, I’ve had a significant number of female friends talked to me about guys they are “dating.”     Here’s a typical conversations:
    “Who is this guy?   Why I have I never heard of him before.   How long have you been dating?   How many dates have you been on?”
    “Oh, we haven’t been on a date, we met on-line and we’ve been texting or e-mailing,” is a typical reply.
    “What? You can’t be dating if you’ve never been on a date, and texting and e-mailing don’t count.   Why haven’t you been on an actual date?”
    “Well, he’s been hurt in the past, had two engagements broken, his wife cheated on him, etc.   He’s just nervous about starting a new relationship and I’ve told him I want to get married.”
    “What?!?! Why have you two shared so much information with someone you barely know, haven’t gone out with and now are not likely to ever go out with?”
    They inevitably reply,   “Well, I’m not telling him anything that couldn’t see in my profile on XYZ dating sight, like wanting to be in a relationship.”
    “Why are you having serious discussions about weighty relationship issues before you’ve even gone on any dates to see if you like this guy?   That seems backwards to me.”
    “He asked. He brought up his last relationship and asked about mine.”
    “So?   Just because he asks doesn’t mean you have to answer.”
    “Well, he texted me these questions, and it would have been rude not answer him or ignore his text.”

    Really?!   Really?! Whatever.
    I think part of the problem is the speed of communication and many people”s perception of urgency because of that speed, creates a false sense of intimacy that doesn’t exist.   And people buy into it.
    It’s not just women saying. “I want to get married.”   There are just as many guys signaling I just want to have fun (by which I mean sex) without commitment.   It’s the age old dance.   But, both parties are asking intrusive questions, and rather than enforcing boundaries, the other person is responding immediately because they think they have to.   This true whether it’s in person, or via text and e-mail.
    Sadly, it’s ruining a lot of potential relationships before they can even go on a date, have some fun, and get to know the other person.   As Evan has pointed out before, what you think you want and what you find you care about once you get to know a person often end up being two entirely different things.

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