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. 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….

  2. 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.

  3. 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.

  4. 34


    What do you do? Just curious.

  5. 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.

  6. 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.

  7. 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

  8. 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.

  9. 39

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

  10. 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. 

  11. 41

    @ Joe, yes! This! He paid and I couldn’t even finish a third of it, so yeah I felt pretty bad… so I offered and he said sure. With a guy friend this would have gone over just fine. But, on a first date… apparently different rules apply. It’s not about the food or the money, it’s about the game 🙂

  12. 42

    Goldie #39, LOL…You do seem like a fun and easygoing lady! I live in Latin America and slightly different “rules” may apply…anyway, if you haven´t read it, I suggest a book called “How to Succeed With Men”, by David Copeland and Ron Louis, it takes you step by step through the dating process…up till long-term commitment! I have read it and refer to it frequently, it has been of great help along with Evan´s newsletters and tips, in being a single mother doing online dating. Again, best of luck to you.

  13. 43

    I find that this “lay everything on the table” advice is very prevalent in religious communities, and even those who are not all that religious can be drawn to this type of thinking because they think it cuts to the chase.
    I also find that the women I know who use this method of dating also tend not to date very much… what I mean by that is that it’s a good year if they have two dates, and many might go for a few years without an actual date. Because of this, they get overly excited when they’re asked out, and put a lot of weight on the idea that this guy could potentially be THE ONE, so they need to find out everything they can before proceeding.
    I think too that women (well, people in general, but I’m thinking of women in this case) have a fear of heartbreak, and the thought is that if they just ask the right questions early, they can weed out Mr. Wrongs and then find themselves sailing smoothly to matrimony with Mr. Right. And while one should have a weeding out process, there’s still the strong change of breakups and heartache as two people date and then realize that they’re just not the right fit for each other. That’s just life… you can’t take shortcuts here!
    When I was dating, I’d estimate that only 25% of my first dates resulted in second dates. And that’s fine… but what if I had put all of my cards on the table on those first dates only to see that most of the guys weren’t going to be interested in a second date, period! Or on a number of occasions, it was ME who wasn’t interested in a second date! Why tell them that I planned to marry, hoped to have two kids, etc., when I don’t even know them or know that I’ll ever see them again, by my choice or theirs? I really see the point of first dates as gateway dates to see if I want a second date. I just have fun on a first date with no expectations, and if a second date results, great. If we get to a third, then maybe the stakes get a bit higher… but still, not yet!
    The only time I ever mentioned marriage and children on a first date was when a man asked me where I saw myself in 10 years (which was an odd question to me anyway). I mentioned some career goals and said that I also expected to be married and have a family. Later in the date, he asked if I had ever considered pursuing an advanced degree because I was “so smart,” and more importantly, wasn’t married and didn’t have kids so I wouldn’t have any time constraints. I said that I had considered it, but in the period of time it took to earn said degree, I expected to be married and have children so I would eventually have time constraints and wouldn’t consider the degree my first priority.
    In that case, I figured, why lie? But other than that, I would never mention either thing on my own on a first date…

  14. 44

    Evan, what a lot of clever, articulate commenters you have here (like attracts like obviously).  This has been a great read.

    Gem @ 18 – spot on, this would be my ideal blueprint for dealing with this stuff. 

    Goldie – I loved reading about your experiences and insights. I have also come to pretty much the same realisation as you but you’re a very quick learner.  It has taken me years of running the wrong strategies.  I hope it pays off for you.


  15. 45

    This is a weird thing that has been happening to me a lot!  I am a 50 yr. old woman, fairly attractive, and a professional.  Many of the dates I have been on the very first meeting (say first meeting from match, or meet them at happy hour) the guy starts asking me WAY to personal stuff…such as how do I handle myself when I am angry, do I have an issue dating someone with a different religious background, if I am not into church, would I have a problem if he went on Sunday mornings and I stayed home….and guess what, there is no way there is a second date! I feel like I am being qualified on the first meeting! They ask too many questions about my divorce, what happened, what my relationship with my ex is like.  Then they text me or call me, and I just don’t respond. 

    I am not looking for a serious relationship.  I am looking to date and the serious relationship will happen when one man makes me not want to date other men.  And I am sure not going to figure that out on the first meeting, or even first few dates. After 20 years not in the dating world, I think the men have become women, and in my case, I am more like the men!  Give it a rest already and just have some fun….like ask me what my favorite book or movie is, don’t be so darn eager to set the hooks! 

  16. 46

    Great advice for the first date as well as through out the relationship and especially if you trying to learn <a href=”http://howtogetyourgirlfriendbacktoday.com”>how to get your girlfriend back</a>.

  17. 47
    Theresa H

    Goldie – I really related to your dating stories (pre: reading Evans Book!)….in addition to the other advice here can I also recommend another good book which helped me ALOT (and I’m pretty sure Evan has recommended on occasion)…its ‘Getting To I Do’ by Patricia Allen. Has a lot of useful information about male / females energy…before this I often got into that trap of trying to be a fun “one-of-theboys” type dates and it wasnt really working.

  18. 48
    Desi Dating Chica

    Evan, I agree with your blog on what is ‘kosher’ to talk about on a first date. My philosophy (and what I tell my friends/clients), is to not talk about sex, politics, or religion on a first date – it brings a level of seriousness to the date, when it should just be about having fun and getting to know each other. Sure, you can be opinionated about the world, but that’s different from having an aggressive standpoint on something, which can become a turn-off for your date…

  19. 49

    I think that you should lay everything out on the table on the first date because if this turns into something serious and something was left out on the first date then its going to come in the light eventually. People should mention there children, previous marriages, Goals, etc. Therefore if there was something that was mentioned on the date that turned you off then you can make a decision on whether or not you wanted to continue seeing this person.

  20. 50

    I had a “meet & greet”/first date last night with a woman from POF and after a bit of small talk including her horrible online dating experiences(she’s been online 4 months !!!)she launches into her “last relationship” that lasted 3-4 months and ended 2 weeks ago.(I first emailed her about 4 weeks ago btw).Sparing absolutely no details sexual and all telling how “great” the sex was,where they’d “do it”,where he wouldn’t wanna “do it”…..yadda yadda yadda and how she ended it because he wasn’t calling her everyday,not returning texts promptly and basically keeping her at arms length for whenever it was convenient for him.To her defense this is all coming from a 48 yr.old woman who is a solid “8” looks wise,separated,getting divorced from a 25 yr marriage and has no recent dating experience.Maybe she was just so “comfortable” with me she thought she could say anything?

    Obviously no one wants to hear sexual details of anyone’s past relationships let alone on a first date/meeting.I’m sure I don’t have to tell this to anyone on this blog but for future readers…………..

  21. 51

    What I find so intreesintg is you could never find this anywhere else.

  22. 52
    Caveat Emptor

    Well, wish I had read this article before going on my first date.  I met a really great guy, great potential and we had a lot of shared interests.  However, I was utilizing the teachings that a renowned relationship expert mentioned that Evan highlights in this article, and it destroyed all levels of curiosity and desire on the man’s part.  

    It’s so true though; this is off topic a bit, but our education system really needs to invest more in truly developing critical thinkers.  (a little projection here can’t hurt :P)

  23. 53

    This made me laugh.  I can’t imagine telling a man that I want to get married on a first date.
    Did have a date though who on the second date bought me a Teddy Bear with “I love you” on it.  It frightened me to death and I legged it!

  24. 54

    Guys need to heed this advice too. I’ve been on six first dates in the last month and a half. Every time I’ve been grilled about my son’s father: Does he live close by, why did we split, etc. I’ve been asked about relationships: length, cause of break-up, etc. I’ve been asked about my childhood: how was it, what was your parents relationship to each other, etc. All of these guys ask me all of these things on the FIRST date! It’s not that I’m not open to share and I do have a healthy ability to be candid and emotionally open, but I feel like I’m on an interview when all I’m trying to do is see if we have some chemistry and have fun together. 

    Today I went on a date with a guy I found very attractive, smart, and who likes doing the same activities as me. I was more excited about meeting him than the others and we had a really great hike (in the rain – which was fabulous). Toward the end of the walk, he started asking me about my thoughts on having kids, what relationships I’ve had, how long, how they ended; that he is very serious about meeting someone and having little ones – whether adopted or fostered (I’ll be 45 my son is a teen, he’s 49 and “fixed”). Maybe I would be interested in adopting or fostering – but my mind isn’t even there yet. I’m so thrown off by these questions on a first date that though I find the guy attractive, I’m not sure I want to go out with him again. the first couple of dates should be fun, in my opinion. If it goes further, then there’s time for such intimate questions.

    I keep reading all of these posts about how women sabotage getting a second date by doing this, but my experience is that men are equally as guilty.  

  25. 55

    Here. Here. Men do this to me. I hate these kinds of dates. It’s like they think we’re going to be together or something so they try to find out all kinds of things. I honestly like hanging out first. A recent one bitterly tried to find out if I was a woman ready to hitch and get settled. I guess I like fun. There are other reasons why men don’t stick around for me (haha)…but I am not the interrogation dater. I went on a first date with this guy today the day after a 3 hour phone conversation that wasn’t too serious. He made jokes about “our interview” (date we had planned), it actually freaked me out, but the conversation was fun so I blew it off. On our date I asked if he had kids and I also really wanted to know if he wanted them. I sneakily dropped this in the conversation: when I have kids….it fit right in with what we were talking about. I saw a change in his eyes but he didn’t say anything. I let it go because I want to spend time with him and the truth shall reveal itself….

  26. 56

    My take on this (and please correct me if I’m wrong, Evan), is that it’s about ATTRACTION and pressure (or, lack thereof). We all pretend that we’re attracted to our list of things we want, but how often have you met the person with the good job who’s kind and interested and respectful and wants the same things etc, but we’re completely bored. Then we meet someone with none of the above (but who is maybe funny and cheeky and cool) and we can’t stop thinking about them. The difference is the first person did nothing to create attraction, whereas the second one did.

    Talking about marriage and a family on the first date is just not attractive (to most people). Even if it’s want you want. It’s like a business meeting/contract negotiation, and that’s the opposite of what a date should be. Being fun and funny and easygoing is mostly attractive (I would imagine to most people).

    Also, I would imagine talking like this creates a lot of pressure for the guy. It would be like a guy talking about some kinky sex move they like on the first date..you may consider it once you like them and trust them and have built rapport, but straight off the bat it would likely freak you out. It’s probably the same for the guys hearing about kids and marriage in the first hour of meeting someone!

  27. 57
    Robert Pattinson

    Make sure that what you say on a first date makes a positive impact on the person sitting opposite you and doesn’t throw on the brakes. Let’s face it, that’s the last thing both you love birds want. The following pointers are good tips for maintaining a fun, relaxed and enjoyable conversation on your date — she’ll feel relaxed and you’ll show her the best version of you, it’s win-win. And, don’t forget, you can always alter these suggestions to suit your circumstances.
    With this thoughts in mind, now it’s time to think about specific first date questions.

    Try these:
    1. Who has been the biggest influence in your life?
    2. What kinds of things really make you laugh?
    3. What’s your favorite place in the entire world?
    4. Who is your best friend? What do you like about him/her?
    5. Favorite movie of all time? Why so?
    6. What’s your biggest goal in life right now?
    7. What is your favorite way to spend a Saturday?
    8. Do you have any pet peeves?
    9. What was your family like growing up?
    10. What were you like as a kid?
    11. What should I know about you that I’d never think to ask about?
    12. Did you—or do you—have a nickname? What’s the story behind it?
    13. Who was your favorite schoolteacher or college professor? Why?
    14. Have you figured out your calling in life? What is it?

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