The Question You Should Avoid Asking On A First Date

I want to talk today about one of those recurring first-date questions: Should you be straight with a guy that you’re looking for a relationship?

This is one of those questions that magazine columns obsess over, yet no-one seems to have a straight answer for it.

And it’s a tricky one: on the one hand, you don’t want to come across as desperate by admitting that you’re on a mission to find the one and will stomp on anyone who gets in your way. But then, you don’t want to have to hide your desires, pretending you don’t want a relationship when you secretly do.

How do we solve this dilemma?

Let me explain my position on this, because it might surprise you: you should not let a guy know that you are looking for a relationship on a first date.

This might seem weird coming from me; I’m always telling people not to play silly games like hard-to-get, and I never advocate using tricks to get a man in a relationship.

So why is it so important not to tell a guy you want a relationship on the first date?

Because you don’t!

You are not looking for a relationship. I’ll repeat that again. We shouldn’t just be looking for a relationship!

What we are looking for is the right person.

If we were just looking for a relationship, most of us could be in one within a week. All we would have to do is dramatically lower our standards and we could find someone who would want to be with us. But that relationship would do nothing for us.

Yet, why do so many of us walk around acting as though just being in a relationship is some kind of worthy goal to aspire to? We completely idealize relationships, we envy people who are in them, we feel bitter that other people have someone and we don’t, as we’ve completely bought into the paradigm that relationships are the pinnacle of success.

And are they? NO! Tons of relationships suck, they have no passion or fun, they consist of two partners who are bored of each other’s company, or who resent each other, or who haven’t had sex in ten years!

I understand though, when we’re on a first date, we don’t want to waste any time. We want to make sure that the guy knows what we’re looking for, and if he doesn’t like it, he can just leave right there and then.

There are two problems with this though:

  1. Just looking for a relationship scares a guy – it makes him feel like you are using him to cover up your own loneliness. This neediness scares him off.
  2. Most men don’t know they want a relationship until they have fallen for you.

Let me explain point 2. Contrary to popular belief, men are always assessing a woman’s relationship potential on a first date. He won’t tell you that because often he doesn’t even know he’s doing it. But – he hasn’t decided he wants a relationship yet.

A guy can be on a first date and be completely excited and blown away by the woman he’s with, and still if she turns around and says “are you looking for anything serious right now?” he’s going to suddenly be ambivalent. Because he hasn’t had time to seriously fall for this woman yet.

When I look back at some of my longest relationships, if you had asked me on the first date of that relationship what I was looking for, I probably would have said, “I’m just enjoying dating and being single right now”. Because at that point, that’s what I genuinely believed. And yet, within a month I was in a relationship.

A first date shouldn’t be an interview for a relationship. A first date should be geared around pure enjoyment – the only important questions are: Do I have fun with this person? Do I feel attracted to his personality? Is there an emotional and physical connection?

This is what first dates are for. Until we know the answer to these questions, there’s no point in asking our date what they are looking for in the long-term.

Besides, as I have repeatedly learned: what men think they want on a first date, and what they want on a third or fourth date can be very different things. Wait until you’re more certain about him, before you find out what he’s looking for.

What other things do you think should be left out of first-date conversation? Be sure to leave a comment and let us know!


Update: Our last UK Women’s Weekend of 2012 is taking place on November the 17/18th in London. This is the flagship event of GetTheGuy where the my team walk you through the complete A-Z of how to transform your love life, in two days of complete immersion. On the Saturday night of the event you even go and practice what you’ve learned live in London’s central venues. You will have never seen anything like it!

Don’t wait till 2013, take action now! Check it out here.


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50 Replies to “The Question You Should Avoid Asking On A First Date”

  • A couple questions that are total mood killers on the first date: Why are you single? Implies that just because you are single you must have character flaws. Then another question that is bad: How many people have you slept with? Is there even a good answer to this question? If you are honest a large number could be an automatic deal breaker. Also, if you have never had sex, you may feel you are being put on the spot. I thinl questions about sexual pasts are just too explicit for a first date.
    P.S. Have you ever done a blog about internet dating, that may ne interesting
    Meghan Salov Whitewater, WI USA

    1. Say something funny like – to find a million pounds under the rug. and then smile and giggle. or ….

      make your face all confused and a bit serious and look around as if you’ve dropped something and say oh … I wasn’t aware that I lost anything – he will totally be caught off guard and love it and it will lighten the mood.

      And then don’t answer the question with anything but a You?

  • I went on a date a few mths back and what put me off was the guy talking about how his Ex was so wrong for him and all the things she did wrong he even mentioned some personal stuff about her which I thought he should have kept to himself. Then he would go on talking about all the mad relationships he has had that got me thinking if its all true he had never learned and fallen for the same type of women that have the same traits in common it really did get me thinking about the kind if guy he is.

  • Hi Matthew, thank you for the article… it seems I’ve been doing something right as I get asked that a lot and always answer that I want a relationship with the right person. :-)
    I also get asked lots of interview type of questions- do you cook? how long are you single for? what was your longest relationship? What are you looking for in a guy? what’s your perfect man? List goes on! Am I right thinking that if a guy asks me those interview questions it means he is looking for a relationship or just asking away with no purpose in particular?
    PS I just had a 4th date with a guy that I realised I don’t want to see again, how to tell him that in a nice way?

  • Hi Matt,

    Thanks! This is so true! What I am trying to do is to have more men to have fun with. Eventually I think then the selection will be in a more natural way. The best match. I even dropped the age thing (younger or older). I am still working on it to have (a lot) of interesting funny men around me and how to handle the situation. I mean to be honest with everybody.

    X A

  • I loved your article as it demystifies the couple which is often thought of as the key to happiness although real happiness can only come from inside and I absolutely agree with you that first of all you should enjoy yourself and have fun on a first date and without asking the question, you’ll often see quickly by yourself if the guy is seriously interested and – more importantly – if you are interested yourself, once you have discovered more about the guy…Other questions that I think should be avoided are those about his previous girlfriends and why it did not work out, what he thinks in general about marriage, children and education – thank u for all your great and very down to earth articles – I love your straight forward and honest approach :-)

  • I think we also should leave out complains about life. if I meet someone for the first date and he start complaining about his work, family, previous relationships .. etc – all of these “negative thoughts” would turn me off big time!

    Thanks Matt for this fantastic tip, your work is highly appreciated :)

  • Great article, thank you Matthew! If I fancy someone I naturally start thinking long term. But you are right, why should I if I don’t even know the person that well?! So obvious but so easy to overlook. You are definitely a master in shifting one’s thinking:-) x

  • This is just common sense. You might be looking for a relationship but that doesn’t mean EVERY guy you date is going to be able to give you the kind that you need. It’s about living in the present and being open and conscious of you want to be treated etc. Yessum.

  • Haha I love the photo, they still got the spark! thanks for the post matt, really enjoyed reading it. Definitely agree about looking for the right person and not just a relationship. Thanks again, am blown away and really inspired by all that you do :)

  • Hi Matthew,

    Honestly I thought “ah another one of those articles about what to say or what not to say”. But then having read it, I find it very valuable that you gave insights into how men think. I also think “Hey I am looking for a longterm relationship, but maybe with this guy, I can imagine a casual relationship”. So it makes sense to just focus on enjoying each other’s company.

    You’d asked feedback in your email about these blog posts. Keep them coming, it does keep us engaged with your material. But also, you are very good in videos, how about video blog posts some time? In fact, may I suggest the topic of your next article? Say I am a single girl who decides to go more actively to the bars. And instead of having to tag people along and confess to them that I may also be looking for some cute guys, I prefer to go alone. What should I then do? If I have a book with me, then would i be too closed to outside world? But if/when I look around, does that also look desperate? Should I sit at the bar or at a table?

    I tried it the other night. I went to a bar to eat cheesecake and tea (you can do this at a bar where I live). And on one side there were more men, but not enough space at the bar. On the other side, there was a space at the bar, but there were all couples. Then a guy came and sat to me. While we had a lovely conversation with him (I can have that with anyone), the guy was 60 and I am 35… So that did not really help. :)

  • I always try to leave my “baggage” behind. Of course my past experiences influence me in someway but i always try to have a positive atitude towards new people cause they can always give me something new, even a bad date i know i can learn from it and still have fun about it later.
    I will never be disappointed with a first date cause there are always a million ways it can turn out to be and i believe it is STUPID to think you can have a connection right away with someone before knowing what you´re dealing with… so… always have fun! And if the person isnt right for me, believe me i will have fun anyways ;)

  • …interesting question…..there are 2 sides of the story here….one for the men and one for the women… here is goes for the men side…..physical contact, dirty jokes, money issues, ex bf/gf stories, work issues, personal issues/problems…..and the list can go on…..point is to be free and express yourself……with no agenda….ultimate goal of course is the possiblity of “meeting of minds” aka “chemistry”…….and don;t forget to enjoy the ride… ;) have a nice weekend guy’s…

  • That was very insightful, thank you.

    Regarding other topics which shouldn’t be brought up on a first date, I believe you’ve said it best when mentioned one should have fun on a first date rather than have their guard up and act like an interrogator. So it’s best to stir away from questions that try to forcefully access a guy’s intentions and motivations.

    I know I wouldn’t like to be on the shoes of someone who’s being scrutinized on a first date — that’s the very reason why I hate job interviews in the first place. lol

  • Exes should DEFINITELY be left out on a first date…at this point you should be having fun and representing what a great person you are to be around.

  • Great article Matthew, I completely agree with you! You have to just enjoy being with who you’re with on a first date without getting tied up in the future – very glad you said this :) xx

  • This comment isn’t exactly about this article but I’d like to see an article about how to get an acquaintance to fall for you. That’d be really helpful.

  • Last time I went on a couple dates with someone, on the first date he asked about my past relationships. I tried to keep my reply short and vague because I don’t think discussing ex’s makes for good for fist date conversation. Second date he asked about my sexual experiences. Call me old fashioned but I also don’t feel comfortable discussing that with someone who is practically a stranger to me. Those are some no-no’s I’ve experienced. I also dislike when people try to make dates into interviews. I think it’s no fun if you tell someone everything about yourself on the first date, and they tell you everything about themselves. That takes all the fun of getting to know someone, it should be something that takes time.

  • My question is this…
    Would the third or the fourth date be a better time to tell the guy that you are looking for an relationship? How does one go about it in stead of being being beating around the bush about it. Because if it were me by this time I would differently know if the guy was interested but if I wasn’t sure what I felt toward the guy yet. I don’t know how I would go about it. Or if I was interested I would be intimidated and not direct of what I want.

  • Agree….Enjoying each others company, having fun, doing stuff. Keeping off the heavy topics like babies and marriage.No interview type, box ticking. Discovering his values and morals in the course of general conversations about life, films, books family, travel etc. His values will become apparent in these interactions, then we can decide if we might be happy together in the long term.
    I found a great guy, so I thought, until I discovered that he had a serious drink problem and I don’t drink. He was the one who said he was looking for a serious relationship. It took a little while to discover the drinking. He wouldn’t have admitted that on a first date ‘interview’

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