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”

  • Matt, your articles are a breath of fresh air when you consider the pap that is out there today. Thank you for yet another great post!

    I’ve been online for almost a couple of years now and I can honestly say I wholeheartedly agree with you about how we put so much onus on “being in a relationship” and not just enjoying the moment or each other’s company. Let’s keep in mind however that guys are interviewing us girls too thou. I have been on so many interview coffee dates where the guy literally lays out his term and conditions it’s not even funny.

    We all seem to be in such a hurry to “find the one” and I for one have finally come to a place where I’m cool with the journey. I’m not in a rush anymore. I don’t care if some guy doesn’t text me back or doesn’t call anymore my life still goes on. :)

  • Hi Matt, I thoroughly enjoy reading your blogs & watching your video – kudos to the entire team! & keep more coming :) because it’s truly another p.o.v. I often haven’t considered … You single-handedly gives me hope that there are emotionally aware men out there, ha aha!

  • As I’ve gotten older I’ve come to understand how important it is to really get to know the person before getting into a relationship. As human beings I think in some way we are always looking we aren’t meant to be alone except those few hermit types who just don’t like being around others, period. Remember to enjoy the moment and don’t become obsessed with getting into a relationship be obsessed with becoming your best self. I personally feel if you strive to be your best and put yourself out there he will find you. :-)
    I hope this made sense I’m doped up on cold meds

  • Hey Matthew,
    I never usually comment but I just had to thank you for this article. I’ve never asked a guy that question but often thought about it. And I think it got to a point where I just saw every cute guy I met as a potential partner. Always wanted to be one of those couples you see in the movies. Completely overlooking the fact that I don’t just want a relationship. I want it with the right guy. From now on I promised myself I’ll just try to enjoy it while it lasts and just have fun like you said. I love reading your articles and since my phone can’t open videos I always have something to keep me entertained on the way to work or just before I doze off to sleep. Keep on with the good work and thank you so much, again. :) x

  • Thanks Matt for all the info and updates you’re sending me. I enjoyed reading every single suggestion you’ve given/shared. Well, about questions that one should avoid during first date, I think it would be better to just keep quiet for a while, let the guy ask first and there and then one would know what kind of guy she’s dating and she can just ask question that would interest the guy. As a girl, I don’t want questions that are too personal during first date..I would like questions that answer spontaneously where the natural me is revealed. This too applies to the guy I’m dating. he should be honest in answering the questions I’m asking and with that I would know his values and interests. Thanks Matt, how I wish I personally know you. you’re a great guy I suppose, the one that I would have as a perfect date.

  • Another few things that shouldn’t be said on a first date:
    1. “Can you believe how hard the dating world is? I mean, I slept with a guy last week who told me he had herpes.”
    2. “Tick Tock. My eggs are drying up.”
    3. “I met my last boyfriend in jail.”
    4. “What is your penis size?”
    5. “I love you.”

  • Hi Matt,

    Thank you for your article. You are right. Seeing other people into a relationship and wondering why it has not happened for me made me upset and even more lonely years on years. I am 35 yrs old and wasted the last decade dating/being with guys who would not either connect or bring me the balance i was looking for. I’ve had low self esteem issues for years because of that.

    Last year I lost my job, my mum passed away and I went into a cycle of depression avoiding friends/family who would flash their happiness to me and shouting me the same questions why you are single, time is ticking about having kids…making me more insecure and depressed and wondering why i was not worthy like them.

    This summer I had decided to go out more thinking not trying to find anyone, and BAM! i went to a social event and two guys were interested in me. The 1st one was loud, making strong eye contacts, touching me/making the high 5 to make sure i would listen to him ; and the second one asked me to keep his bag while he would go around the venue.. after a while i looked up and the second guy was looking at me from a distance while talking to his friend. I thought that was odd. after a few minutes i felt a body contact on my left (the 1st guy was still talking lots on my right) and there he was very close to me (legs were touching). I looked at him and we smiled while still looking. I got the message and he sat there next to me quickly until he decided to leave… I was gutted seeing him leaving and not having had a chance to taking to that 2nd guy.

    The next day i woke up late, checking my email and that guy who came close to me sent me an email through the membership contact list (at 6am on a week-end) asking me out for a drink saying wanting to finish the conversation (that did not really had).

    On the 1st date, he told me straight away “i want nothing from you’ while pointing his hand at me. That killed me inside… but i kept a brave face and tried to enjoy the moment. It lasted an hour or two then he directed the conversation into the topics he wanted (i realised he had researched about me online… and i starting doubting his real intensions..). He kept saying he was happy in this own, not looking for anything.. Before excusing himself he asked me if i was single. I laughed and while having a surprise face and answered there is no guy. He did not believe me and there started the questioning… when was your last relationship, why it did not last, who was the guy, why you had not sex since… then he concluded I had issues/baggage saying “The pattern for some people repeat itself and these kind of people cannot see it of move forward’. I thought he was an A_ _ and that we would never see him again. He sounded cold and calculating and he made me feel i am not a worthy person and he sounded like he was too good for someone like me.

    I said bye and he asked to meet again. I said yes, thinking hummm it did not go that well and he is too judgmental so forget it. Guess what.. he texted again after a week to meet up. After all I thought he wants nothing lets just have a good time. The second date he was more opened. We talked about his job, politics, his views… at time he would be a bit sharp telling me i did not get his point. There he was again.. being rude. I thought this is it is not the kind of energy i like. It was time to leave and then he asked me to join him as he was hungry and as he travelled from far to meet me so i accepted.

    We went for a meal, I let him decide on the meal to share (as i had paid for the drinks earlier). He recalled everything I said on the 1st date, he came with more questions and opinions. He appeared extremely negative about relationships, marriage, the bad experiences for his friends (I thought because he was talking about himself) and then he brought up the sex subject. He shouted the SEX word at least 3 times within 15 seconds loudly in the restaurant. I was was sooo embarrassed.. that was laughable. i people around us were looking. He then said he knew people on a relationship who sleep around that that is a good thing as nobody in life should commit to anything. Then he told me he had a GF but my impression was there were still together and he wanted casual fun. I stood my ground and told him sorry but if that opened relationships that his are looking for, then they should be to Brazil as the over there I was offered sex all the time and people are very opened/flexible. He was not happy about my answer and I gave him an eye contact saying i am decent women and i yes can be rude as well.

    We left and we never met again.

    I learnt in this process
    – go with the flow and listen to watch the signs while remembering to actually watch the signs (some men are manipulative and liars)
    – not to accept second best and equal their energy/confidence
    – look beyond a male pretty/sexy looks and when he flashed it to you, do not fall into the trap
    – if he is not a decent man he will reveal it by himself as he had a game plan and shoot him when you know this not it so actually remembers they are decent woman who deserve the respect they gave them at the 1st place.

    Of girls, i will attend November the 17th event and I look forward to learning more from Matthew’s team as i am ready to find the right guy and not waste any more time with losers.

    ps: no offence about Brazil, it is a beautiful country with beautiful people. I only told him that was an example because he had not been there.


  • Thank Matt this is really inspiring!! I never really ask questions, but I do often see nice guys I meet as a potential partners and I should learn to just enjoy myself without expectations. Thanks again!!

  • Hey Matt,

    I like reading your article and it interests me much………
    I wish all the guys should be honest with their partners…
    Anyway, thanks Matt for the great advice ……I wish it will work when I have my first date………

  • hi Matt. Thanx for your acticle.i felt so bad when a guy on our first date ask me when last did i hv sex?, do i love sex?. Thank u again 4 ur concern and cares.

  • Great advice Matthew. Completely agree that people are not looking for a relationship, so if we keep deluding ourselves with that illusion how are we ever going to be genuine?

    Reminds me of the philosophical questioning Michael J. Sandel plays with, which I absolutely love – get what you’re arguing for right, or you’re never going to get it!


  • Also, I would say it’d be helpful to talk about what it means to be looking for the right person to spend your time with instead of a relationship. What’s the focus difference?

  • Hi Matt,

    This is a good one,i like it.

    What if a guy tries to get physical on the second or third date .Do you still have to wait to ask/tell the relationship quastion?

    This applies also to guys who ask you tell them that you love them on the first date.It puts me off.

  • Hi Matt and team!

    like your articles and videos in general, but have some concerns with the last one, so decided to comment.
    It’s all good about just having fun on a first date. Then comes second/third one and here a difficulty emerges.
    My situation: I’m 31 and have a son half of the time. The actual time that I can spend on dating is limited. The tendencies with dates look like:
    1) We are not a match/don’t like each other. — Normal situation, nothing to discuss.
    2) I’m asked for sex on a first date. — A huge turn off for me; I don’t continue communication with that man.
    3) I’m asked for sex on a second/third date. If I refuse, then I don’t receive any more attention form the man. — Understand them perfectly, we just have different goals for dating.
    4) We mutually like each other. But relationships turn to dialogues: “Are you free tonight? Yes? I come to your place (to f**k you) at 8. — I’m not happy with this type of dating either.

    It continues for the last three years. I’m tired of this label “single mom is only for sex/single moms crave for sex, they are easy ones to get” (I’ve read it on guys forums)

    So, how can I save my time on players if I won’t tell them that I want a relationship? I understand that guys probably don’t want relationships immediately, but at least I hope they are mature enough to realize the possibility of it for themselves?
    If a guy goes around with the flag of casual dating, it’s ok, but I don’t want spend my time on him, even fun time.
    What’s your advice, Matt? I’m not in a rush, my life goes on with my son, friends, job, but personal life seems to be over. It’s sad.

  • Hi Matthew,

    Can you write about how to know if you’re being used as a rebound? It would be very helpful!

    Thanks :)

  • what if he asks you, are you looking for a relationship right now?
    i find that awkward and like i’m backed in a corner…. i have a mini freak out.
    and then they ask me why am i single? then after my answer i havent found anyone i wanted to share my life with yet and having fun.
    they then ask me what were the men like or were they all idiots? my answer never seems enough for them.

  • Hey Matt,
    It was so interesting and useful article. I will try the things, that you wrote.
    I think this shouldn’t be asked on a first date.
    “Can I kiss you?”-If you met the person 15 min. ago. If it is at the end of the date, I think it’s ok. In my opinion, if he asks this too soon first, the man wants to skrip the conversation and don’t want to get to know you as a person.Second,I am sure he wants to go faster to the sex part.
    I had a date with a person, who asked me this 2 years ago. After he started to kiss me, he didn’t let me to tell a word. I understand everything clearly, when he wanted to invited himself to my home.I refused of course. After that, he walked alone disappointed, but I was happy.He knew what he wants, but I knew for myself too and I didn’t let him to use me. I was so proud of me.:)

    PS:Your advices help me a lot.Thanks that you doing this. Have a nice day! :)

    Yours faithfully


  • awesome article. I feel like i m back on track to finding my mr right =)

    relationship doesn’t mean anything if the person isnt right. us enjoy the date.

  • Wow, guys I love your site, blog, videos, everything. Your attitude is so bang on and exactly how it should be, I hope you reach more and more women with your work and also men !

    I genuinely believe, especially here in Ireland, women and men can’t just enjoy been single for what it is at that moment and just know yes, some day they want to meet the right person for THEM, not the right now man to fill some ridiculous insecurities at the time.

    I have some thoughts and blogs myself on this topic from time to time, would love to know what you think xxx

    Keep up the great work, and try inject some into Ireland when you can ;)

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