[Video] How Long Should You Wait Before You Sleep With Him?

Here’s the latest video from the series I created with Three Day Rule. It’s called “How Long Should You Wait Before You Sleep With Him?”

In it, Kate and I discuss how early into a relationship it’s acceptable to have sex with a guy. We both agree there is no right or wrong answer to this question, but we also strongly suggest you’re aware of the potential consequences of getting physical too quickly.

Join our conversation (29 Comments).
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  1. 1

    I believe that many women don’t know themselves very well, wish that they could have expectations-free sex and tell themselves that they won’t get hurt.   So they sleep with a guy, feel bad when they never hear from him and then label him a jerk.

    Ladies: I don’t care who you do or don’t f*ck.   Just take responsibility for your own actions and emotions.   Don’t blame men if you have commitment-free sex and he acts accordingly.

    1. 1.1

      Henriette!   I’m shocked!   Shocked I tell you!!

      1. 1.1.1

        Shocked that you agree with me, @Rusty? 😉   Or shocked that women might sleep with a guy who walks away after sex?

    2. 1.2

      *APPLAUSE* Beautifully stated, Henriette! Thank you!

      1. 1.2.1

        See, @Buck?!   Trust me; we have more in common than you might imagine. 🙂   I don’t like whiny people ~ male or female ~ who blame others for their own issues.   *hugs*


    3. 1.3

      And sometimes–and this is rare–a woman thinks the date will   end in a makeout session, but the makeout session turns out to be so surprisingly hot that she says, “Ah, to hell with it!” and sleeps with him anyway.

      1. 1.3.1

        I don’t know how rare that is, @Emily.   Many of my friends have done this at least once.   But then it usually bruises their egos, ever-so-slightly, when the object of their momentary lust doesn’t call them afterwards.   It also makes some men believe that all women will have casual sex with a guy they find hot enough, and that if a woman won’t have casual sex with him it’s because she considers him an unsexy chump and will keep using him for free dinners until a guy she considers hot comes along.

        1. Emily

          I guess I was referring to a situation where a woman is dating the guy and is on date 2 or 3 or 4 with him and ends up sleeping with him for the first time a lot sooner than she expected to because the physical part of it turns out to be so hot. Somebody makes a move and – KABLAM! – all her reason goes out the window. The heat of the situation is rare. Of course, that guy can disappear on her, too,   just like a pick-up at a bar could. There is no guarantee.

      2. 1.3.2

        Emily, it works both ways 🙂

        In fact, the situation you describe has been the story of my life.   Date 2 or  3, always a pause at some point in the making out to see if she is sure, or more likely she asks me  if I want to.

        It has worked out well, that is I don’t sleep with someone if I don’t hope and plan on staying with barring some horrible weird event in bed  (and it has never been anything but great).   Or we both realize this is just crazy lust talking, and agree to no expectations.     Not a fan of that, but have done it.   I’ve been loved and left myself, but never done the loving and leaving.   And not a player, always monogamous, usually together for 6-18 months after.

        I guess short answer is, have high standards to start with (especially in emotional and intellectual connection), be open and honest, always pause to make sure you both really want to do this, and be safe.

    4. 1.4

      How long should they wait

      1. 1.4.1

        they shouldn`t at all ahahahahha

    5. 1.5

      i agree…..


    6. 1.6
      Truly ashamed...

      I feel so stupid. I am in my mid thirties and have only just started to truly realise   and understand from blogs like these why sleeping with a guy early on is much more likely to lead to heart break. I have been hoping that one of the guys that I   was attracted to would be attracted to me and that we would just end up being together and things would simply fall into place. Boy was I   wrong. .. It’s horrid knowing that I wasted so much of my life being used by guys that simply wanted what was between my legs. And knowing that I never invested   enough time wisely closing my legs to   meet and get to know Mr Right and avoid all of   the heart ache. Feel so dumb.

      1. 1.6.1

        Don’t feel stupid.   I also made a lot of mistakes in dating, and only found real love when I turned 35.   I’ve seen women much older than us make mistakes in dating too.   We all learn at different rates.

        Definitely try to learn from any mistakes you made, but also don’t keep beating yourself up over them either.   It’s never too late to learn from mistakes and find love.   I know people who finally found love in their 40s, 50s and beyond (and some after very nasty divorces too).   In some ways, finding love at older ages can be more challenging…but it’s not impossible either.

  2. 2

    That’s an easy one, since I’m waiting for marriage! Lol Makes it a lot less confusing.

  3. 3

    Well, several men have made fun of me for not sleeping with them within 3 dates. They call me names like “Old Soul” and “Old School”, and say I’m “ridiculous” for making them wait until we know each other a little better.   Men can continue to call me every nasty insulting name in the book.   I still will NOT give into them, no matter how bad they make me feel about myself.

    1. 3.1

      Woof! A guy ridiculing me for my feelings and boundaries would make the decision about when to have sex with him (never) oh so easy!

    2. 3.2
      In Not Of

      I might be misinterpreting your last sentence, but why let them make you feel bad about yourself? Don’t internalize that nonsense.   The person that mocks you for standing on principle is showing you exactly who they are and doing you a favor by revealing themselves early on, before you emotionally invest.

      1. 3.2.1

        You didn’t misunderstand my last sentence. You are spot-on and I agree with you.   I’m just questioning whether or not I need to change my principals.   Even my gynecologist said that everyone is having sex within 3 dates (well everyone except me).   I think Evan gives the best advice here.   It really does boil down to whether or not you’re comfortable having sex with someone who might not call you again.   I just wish men could be more gentleman-like and say they understood when I tell them it’s too soon, instead of insulting me.

        1. JustAGuy

          If he insults you forget him.   A guy who likes you is happy to take it slow because he likes talking to you, you make him feel good without sleeping with him.   YEs. he’ll want the total emotional and physical intimacy package eventually, don’t we all, but if he does not feel like you are using him then he can be patient.

          That’s critical though, if you expect him to pay for all the dates, and believe he should be an emotional dumping ground for the bad things in your life he’s going to wonder if you are using him.   Paying for the whole date yourself shows that you really are into him, you value him for him not the material things he can provide.   If you can talk about the things that fill his soul, then he will want to see you just to talk.   You also want to see if he can do the same for you.

          One thing a lot of guys fear is after they sleep with you, all of a sudden you will become a clingy, needy person who expects them to take care of both your material and emotional health.   A longer courtship where you can show you are not like that is valued, just be upfront.

          Don’t change your principles.

    3. 3.3
      John williams

      I’d be too embarrassed to give a woman a hard time if she didn’t sleep with me within 3 dates.   It’s fine if she does, but if she’s not comfortable / into it yet, it’s her call!   (Then again, I think I’m an “old soul”!)

  4. 4

    It’s no different for the younger crowd than the older crowd.   Guys want sex and they always have, it’s up to the women to say yes or no.

    What’s missing from the video  are the nuances of saying no  the EMK  way, where there’s no rejecting, no anger, no shame for anyone involved.     It takes a little practice but it works.

    If a guy starts calling you names for having boundaries,  you have your answer…he’s not your guy.

  5. 5

    I think women don’t know what they want or how to communicate what they want.   They take a lazy approach to dating, let the guy do all the courting, and then are shocked when he dumps her after sex.

    If a woman wants a relationship, then she should treat it as pursuing a PARTNERSHIP.   That means putting in equal effort, and communicating your expectations beyond sex.   A guy’s goal is sex, and will do anything to look impressive, but for a relationship to last after sex, there has to actually be a “Relationship.”

    I think women make the mistake of believing there is a relationship, when in fact there is no relationship, and its just the guy doing most of the work.   If a woman wants more than sex, then she can’t pull the bait and switch.   She has to place herself as an equal active partner in the courting process.

    Women make the mistake in thinking that Sex = marriage/LTR, and that’s a Disney fantasy.   In this modern age, casual sex is the new normal.   A woman has to take charge if she wants something more.

  6. 6

    I agree with Henriette!   In the moment, it can be very hard to assert your boundaries, and I have learned that it is up to you as a woman to draw the line or take responsibility that you didn’t.   At the end of the day, as aggravating as it is that men will continue to push (within the same hour) when you set those boundaries, it is ultimately your call.   Better food for thought: maybe you need to be more aware of putting yourself in situations that lead to sex if you find that you lack the willpower to draw the line.   If you’re not ready, and don’t have the commitment (honestly, the emotional connection is the key more than mere words) that you want, don’t go to his place or invite him to yours!

    I do have to disagree with Jack a little bit, though.   You may not be one of them but many, many men will perceive a woman chasing a man at any level in the early stages of the relationship is her being overly needy or clingy.   Sorry, that’s just biology.   There is a lot to be said for having the strength and discipline to just lean back and let a man do what his biology dictates.   For the woman, too, this is important because the man is demonstrating his level of seriousness as well as his ability to provide.   Again, this is just biology, trust me, I would be much more comfortable going after what I want and meeting a man half way as you suggest!

  7. 7

    I suppose you can say its okay for women to be “needy or clingy” after sex, since many women expect to have more than just one night stands, so in a woman’s mind she will logically/rationally think that the man will want to come back for more sex, so she can start being more needy and demanding in the relationship?   While a man might logically/rationally think that he just wants one night of sex, but doesn’t like her personality or want the demands and expectations of a long term relationship.   A woman may be needy for a relationship, and a man might be needy for sex.   It seems that those are 2 different goals, and men fake wanting a relationship while women fake wanting just sex.   I’m merely saying that women need to be honest and unafraid to be demanding/needy/clingly because it will scare away the men who don’t want a relationship, while the men who want a relationship will stick around and want to be with a clingy-needy woman because he actually enjoys being in a relationship with her.   If she wants more than just sex, then take away the sex and work on building a relationship foundation based on friendship.   I think most women expect sex to lead to marriage, and get mad when it doesn’t.

  8. 8

    Great video Evan! Well, as a girl in her late twenties, I would say I have slept with men based on chemistry alone and I was rather equivocal about it. I was never really hurt because I knew I gave into the temptation and I would own whatever consequence that followed; but in the other hand those experiences accentuated what I really want, which is a relationship. Those encounters never materialized into anything more than hookup. Some might have different experience; and I am totally fine with girls who are comfortable with hookups. In the end, I kept feeling like I kept eating sardines on saltine crackers in lieu of gourmet sushi which I am really craving for, and while they make me less hungry doesn’t mean I am satisfied. Along these years I have learned to focus on what I really want and stop focusing too much on deciphering the “man code”. 😀 I think the best thing of being single is that you can develop a relationship with yourself and that in itself, is pretty rad.

  9. 9

    Thank you Evan for your blog. Re entering the dating scene at 48. It makes me realize how nieve I am.   Nothing makes more sense than when yoh said point blank, “men ask you out because they want to have sex with you then they fall in love. ”

    Thank you,


  10. 10

    I would disagree with the whole “men ask women out for sex with women then to fall in love”.   I don’t think one can make a blanket statement like this.

    Not all men are the same nor are all women.

    Some men ask women out because they’re truly interested in them as a person and not for just sex.   I know I do, many times I don’t have sex with the women I date.   Sometimes it’s just nice to have a nice conversation and laughs with a woman over dinner.

  11. 11

    By your 40s you know when it’s best for you.


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