What You Should Be Talking About On the First Date


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. 21
    my honest answer

    I totally agree about announcing you want marriage and kids on the first date as coming across as needy (and more than a little nutty, to be honest). The best thing you can do, if you’re nervous, is to ask lots of questions about them. Everyone likes talking about themselves, right?
    Thanks for debunking an all-too-common myth, Evan.

    1. 21.1

      “Everyone likes talking about themselves, right?”

      I think that advice is overdone. No, not everyone likes talking, let alone love, talking about themselves. This is something that has been shoved to death down our throats and just overused to the point of being annoying to the person who now feels like they have to talk about themselves incessantly simply because the other person asked.

  2. 22

    I’ve always gone by the “never discuss sex, religion, or politics in polite company” rule. Those topics when discussed with someone new can easily make for an uncomfortable situation, and I’ve also added other things such as marriage, medications and finances that I personally have no place in polite conversation. I just think those are very uncouth topics. I also don’t think it’s fair to interrogate people with questions you yourself probably wouldn’t like to feel obligated to answer on the first date. I know questions about my political affiliation and finances would have me completely turned off and eager to head for the door. Maybe it’s time we revised the “polite discussion” list of topics?

  3. 23

    In my experience (and no this is not exactly a shameless plug for Evan’s work, although it should be, because he taught me) by having an engaging first phone conversation with a new online man, the first date is well set up for fun.   It’s not a time for heavy anything, but a time to begin observing who he is and how he shows up.   Ultimately, I’m looking for congruence of actions “in person” to the words he has written and spoken to me before we’ve met.   An assessment of character happens over time and builds with all the little observations.   It would be premature for me to share heartfelt dreams and desires with someone when I don’t yet really know WHO they are.

    The second piece of dating advice that has been helpful is that I should only say “yes” to dates that will be fun for me, even if my companion turns out to be not to my taste.   Activities that if I were doing alone, I’d have fun.   This keeps me appreciative of the time spent on the date, his efforts to plan something that will please me, and ensures there is an enjoyable activity that we can both focus on, instead of a mutual navel gazing conversation.  

  4. 24

    Finance, past relationships and past break-ups/divorce are a no-no for first or even second date convo.
    I met a very nice man. We had a lot in common, including amazingly we were exactly the same age (DOB within a couple of weeks of each other), had got married in the same month 14 years prior, had our honeymoons in the same country, our children were also born within a month of each other, and we had separated from our respective spouses within a month of each other. So we started talking about our respective divorces (on a first date no less!!) and he volunteered information about the asset split he and his ex were negotiating X%/Y% and I blurted out “Oh, you are very harsh on your poor wife. I am going for Z%” (higher than what he was offering his ex). He said “Gee, I’m glad I didn’t marry you first! You would leave me broke!”. So I immediately back-tracked “Well, I know I’m not going to get it, but that is what my lawyer suggested as a starting point for the negotiation.” Bad idea!! From now on I am absolutely steering clear of talk about my ex, divorce and finances…

  5. 25

    @Evan – “he’s being interviewed like an intern who’s applying for a lifetime job at your company”

    That’s  exactly how I feel when I finally get a response from a woman I’ve emailed online.After the first email,with the second email the”qualifying”(interrogation) process starts.Usually they’ll dance around the”what do you do”question a bit or come right out and  ask it along with other interview(interrogation) type questions.In a first email  a woman last week asked me “how come you don’t have kids?”  Some of them  make me feel like I’m applying not for a”lifetime job”but just applying to see if I MIGHT be worthy of a “15 minute phone interview” let alone the holy grail of them all “meet for a drink” where of course I’ll be interrogated further to find out if I’m “first actual date” material…LOL Which brings us to the topic at hand,first date(interrogation) err….pleasant fun conversation.
    I wonder how long it’ll be before everyone’s “LinkedIn” and Facebook profiles will just be part of their Match/Plenty Of Fish profiles??It’ll save a lot of interrogation and time.

    1. 25.1

      I am a woman and have received those same questions  during the first phone contact.

      I have had men from online dating ask “so why have you never been married?”   and “did you never want kids or were you just very  focused on your career?”    Awkward questions that are difficult to respond to in the short-breezy format that I usually try to maintain during  the first phone contact.

      My goal is to maintain a breezy, pleasant conversation centered on the mutual interests I identified from his profile.   If he brings up the heavy topics, then I will respond but try to keep my answer limited, pleasant and devoid of details about past breakups.


  6. 26

    I have always had divorce come up on the 1st date. Shop talk, I guess… Never did me any harm that I know of. Then again, every man I’ve dated envies my ex because we just each took our own and walked… One guy asked “can I divorce you?” 🙂 I guess it depends on the details. If it was civil, and you’ve remained friendly with your ex, then why not.
    Likewise, religion and politics always manage to rear their ugly heads in first-date conversations. I kind of see where the guys are coming from. If your date thinks the earth was created in six days, better find that out sooner than later…  
    @ Annie #20:
    “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.”
    Unfortunately, in my case, I was being myself. When you’re around two teenage guys and a male dog at home, and in a mostly-male environment at work, over time, you tend to grow balls of steel, lol And that appendage does not go over well with the men on dates at all! So I’m going to have to soften my image a little and remember that I am on a date being wooed, not at a happy hour talking shop with the dudes, or at home trying to keep my boys organized 🙂
    @Steve #15 – I date geeks. So there are no true alphas or omegas in my circle. I meant in the relative sense – the more or less confident guys, on one hand, and the more or less submissive ones, on the other. My apologies, this was probably the wrong use of terms alpha and omega, should’ve been more specific.

  7. 27
    Bree Talon

    Plus one for making the point about critical thinking…something we should NEVER forget to do.

  8. 28

    @JB #26
    I appreciate why you felt interrogated. What would you have considered appropriate low-pressure questions for a woman to ask you in a first and second email, that are different from what she can read in your profile? What about face to face on a first date, if you have actually met in person, not online?
    I have not dated actively since my separation (would prefer to have the divorce final first), but am feeling very anxious about what would be appropriate to ask and appropriate topics for conversation. When I meet people organically (not with intention to date them), I tend to come across as very flirty and we chat and laugh a lot, but then I realise I have not actually found out anything about the man. Any pointers from a man about appropriate questions that they would not mind answering early on would be appreciated.

  9. 29

    Goldie #2

    I think you did the right thing in trying really hard to relax, and not try so hard!

    First dates are for assessing how compatible you are and if there is any chemistry. You are on dangerous ground when you communicate too much negativity and too much insecurity early on. I usually don’t get any more personal than talk about family, our work/hobbies, and general interests on first dates. Most first dates don’t progress all that far, so why reveal too much too soon?

    Also, I think people communicate in code early on. You don’t want to tell someone you don’t find them attractive, so when he asks if you’d like to go out again, you say yes, even though you didn’t feel much attraction. Ot he feels that way about you, but says he’ll call anyway. That’s why a man can tell you he feels “no spark” after the first date, but still ask for a second and third, hoping he might change his mind. It’s up to you to decide if that is a risk worth taking. If a man is into a woman, he’d never tell her he didn’t feel a spark after the first date, he’d be trying to impress her and getting her to like him!

  10. 30

    smile, nod, be perky. that’s the approach i use.

  11. 31

    @ Goldie #27

    “…. a mostly-male environment at work, over time, you tend to grow balls of steel, lol And that appendage does not go over well with the men on dates at all! So I’m going to have to soften my image a little and remember that I am on a date being wooed, not at a happy hour talking shop with the dude…”

    Yup. Me too. I’m learning to mentally and energetically reframe things when I meet a new guy after work by deliberately changing out of my work clothes first, often choosing to wear a skirt. That helps me leave my man-self at the office….

  12. 32
    Karl R

    Sacha asked: (#29)
    “What would you have considered appropriate low-pressure questions for a woman to ask you in a first and second email, that are different from what she can read in your profile?”

    I’d recommend asking questions that someone will have to answer with a story. It’s non-threatening, and you can start to learn a little bit about his personality by paying attention to the details.

    A person’s profile is a great place to start. If  a person has “fencing” listed as a sport that they enjoy, ask  him (or her)  how  he got involved in fencing.

    Look for something unusual in  his profile, and find out the story behind it.

    Better yet, figure out what  he (or she) is  passionate about, and get him talking about that.

    These things work for normal small-talk in a non-dating environment. Instead of asking what people do for a living, I prefer to ask them what they like to do when they’re not at work.

  13. 33

    I think people reveal themselves and their intentions very quickly in the WAY they talk about things – its not necessary to grill them on specific “topics of interest.”. Its not so important WHAT you talk about, just get them talking and you’ll find out everything you want to know about them – whether they’re sceptical or innocent, generous or mean, serious or playing around.
    I am going on a first date on sunday with someone who contacted me online. He mentioned in his profile that he has a motorbike, a place in France and likes fine food and wine. I intend to lead with the motorbike. Get him talking about something he’s enthusiastic about, and you’ll learn a lot. Does he tell you how expensive it was, or complain about the running costs? Does he enjoy being at one with nature alone on wild mountain biker trails, or spend every weekend with a gang of 20 biker mates he’s known since he was 15, camping in the rain and geting drunk? Or does he whiz around Europe looking cool and staying at the best hotels?
    I’ll also say – ” So you enjoy spending time in France?” rather than “tell me about your place in France” – which might sound like I was looking for free holidays or just interested in someone with a second home. When I get him talking about France, I’ll find out if he just likes the cheap wine and hates the locals, or is an art buff, of just likes going places with hot weather. I’ll also find out if he makes me laugh, telling crazy stories about his manly escapades, or bores me with details of road networks and flat tyres.
    At the end of the day, what you want to come away with  from a first date is a sense of who this person IS   in themselves, and whether you’re ATTRACTED to them. If you’re not, it doesn’t matter whether they’re interested in marriage or not!.
    As to their “intentions” these slip out without men even noticing if you just let them talk. Not so long ago I met a guy who had only recently moved to my area, but when talking about his job in the ski business came out with the fact that he was really keen on the idea of opening his own ski shop in the Alps. I have no intention of moving to the Alps, and a guy who was interested in settling into a serious relationship would not have blithely mentioned moving away on our second date! I rest my case.

  14. 34


    What do you do? Just curious.

  15. 35
    Karl R

    helene said: (#34)
    “I have no intention of moving to the Alps, and a guy who was interested in settling into a serious relationship would not have blithely mentioned moving away on our second date!”

    I seem to be missing something. Is there something about the Alps that would prevent him from settling into a serious relationship with a woman?

    Obviously he can’t settle into a serious relationship with you and also move to the Alps (though he may have been unaware of that on the 2nd date), but I’m sure he could find some  women in my neighborhood who would be willing to move to the Alps … and it sounds like you live much closer to the Alps than I do. And even if he can’t find a woman in your area who is willing to move to the Alps with him, he can continue pursuing a serious relationship after he moves to the Alps.

    No matter how interested he was in a serious relationship (in general), I wouldn’t expect him to be interested in a serious relationship with you by the second date. I only know a couple guys who are likely to decide that they want a serious relationship on the first or second date … and they come across as unstable/stalker types.

    helene said: (#34)
    “As to their ‘intentions’ these slip out without men even noticing if you just let them talk.”

    That sounds like the sort of thing I  might let “slip out” intentionally.

    If it’s his dream to open a shop in the Alps, he’s probably willing to postpone a serious relationship in order to fulfill that dream. He could want a serious relationship, but still have it be priority #2.

    In many ways, he sounds like the women who bring up children on the first couple dates (though he sounds more subtle). If a woman isn’t interested in moving to the Alps with him, he’s not wasting  more than two  dates on her.

  16. 36

    @Goldie #2, You give your dates your leftover dinner?? Too motherly for a first date, in my opinion… and kind of gross… sorry, but I ´d never accept leftovers from a first date! Having fun on a date is one thing, but overly pampering a man on a first date is a no-no, in my book… Best of luck.

  17. 37

    @Sasca #29,Karls’ right try and keep it light,fun,and upbeat.Ask about hobbies and interest’s that are in his profile etc… I’ve always found that when a woman says or asks “tell me about yourself,do you enjoy what you do?”It FEELS less judgemental than the harsh tone of   “What do you do for a living?” which insinuates that if she doesn’t like the answer I’ll never hear from her again. Which happens to me about 50% of the time.

    In this day and age with online dating now versus the way we used to do it most of the normal first date conversations take place during the email exchanges leading up to “phone call worthy” or “meet & greet” so that when we actually go on a first date with someone you’re past all the “what can’t we talk about”stage.On the other hand on VERY RARE occasions I’ve had women just email me on the second email and say “let’s meet for a drink” even though we’ve established no rapport whatsoever.That’s when you really need old fashioned first date conversation skills…lol

  18. 38

    @ #37, LOL it was on one occasion and it was a shared appetizer… finger food 🙂 But yeah you’re absolutely right that it probably came across as over-pampering. Even though he thanked me for it next time we met.

  19. 39

    I personally don’t think there’s anything wrong with giving your date the leftovers, especially if he paid for dinner.

  20. 40

    I remember a mid 30’s woman say, ” I want a little girl”,   when I first approached her.     Never said hi, good morning, etc…nothing else.   On our first date, I paid for dinner, and she had to go outside for a smoke, ’cause, “no one buys her dinner”.   Although I must say, her kind, are far and few, in my life.  

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