When to Have Sex with Him

When is the right time to sleep with a guy?

This topic often creates a lot of confusion, so I wanted to clarify some of my thoughts on it…

Does sex build connection,
or does a connection make sex even better?

Leave your comment below


Last week we did a video on how important genuine, authentic warmth is in the early stages of meeting someone and dating and I talked about it as being that mid point between being overtly sexual in a way that can hurt your chances and being so cold that someone doesn’t feel like they have a chance. Now we got a comment in response to this from a woman named Paula. I’m going to read her comment right now.

“Matthew, it may not be your intention but you perpetuate the myth that sex should be earned and if a woman is looking for a relationship, she should wait. Men are rather “easy” and (from my experience) they create all the sexual tension very early but somehow you wouldn’t give the same advice to them.” We’ll come back to that in a minute. “Why not aim to change the sex-negative culture that we live in and tell people that it doesn’t matter when they decide to have sex? People have sex for many different reasons. Power dynamics should not be one of them.” Agreed. “If someone wants to stay in your life after the first night, they will. If a guy thinks that having sex with him quickly means that I’m not girlfriend material, great, I don’t want to be with a person who holds this belief and is happy with a double standard. It also makes me sad that someone may think that a sexual interaction WITH THEM makes another person less desirable in the long run. I enjoy your videos. Keep doing great work. It would be great to unpack modern sexual dynamics even more.”

Firstly, thank you Paula for your well-lettered comment. I really enjoyed reading it and I thought this would be an interesting opportunity to shed some light on my views on sex to clarify that position because I feel like it does create some confusion for people.

Now, Paula, I believe you’re referring to this part of the video:

Very often if we have sex before there is a connection that doesn’t feel earned as a level of intimacy. It feels cheap and if it feels cheap it feels disposable.

Now before I go any further, I did also say this in the video, which I think is important.

So now what happens for a lot of people is they get sexual very quickly and then find that it doesn’t go anywhere–which, by the way, is absolutely fine if you’re just having fun being sexual with people.

The reason I play you that is because I first want to stress I don’t care when any gender has sex with somebody else. That doesn’t matter to me. I also want to say before I go any further that, Paula, your instinct that I wouldn’t give the same advice to guys is actually not true. I’ve given guys the exact same advice. If you really like someone don’t be thirsty. Give it a minute. You lose nothing by taking a beat before trying to rush home with this person. But, by trying to rush home with this person, you might actually cheapen this thing that you want to mean something.

Most of us here, I assume, are old enough to know or to have realized that sex doesn’t intrinsically have meaning. Sex can mean something or it can mean nothing. And of course when we do have sex with someone very quickly, if we treat it like it’s the fourth drink of the night, then it will be as important as the fourth drink of the night.

Now it does raise the question, “Does having sex with someone build a connection quicker?” and, in a sense, it can, but it’s a specific kind of connection. We can build a physical connection with that person. We can quickly build chemistry with that person on an intimate level. And especially if the sex is good then you feel like you have something with that person. But that doesn’t mean you have an intellectual connection, it doesn’t mean you have a worldview connection, it doesn’t necessarily mean you have an emotional connection, it doesn’t mean you have a values connection, it just means you have a physical connection.

Now, plenty of relationships can survive for quite some time on just a physical connection but I know many of you will have tried that game and realized ultimately it doesn’t satisfy you. It’s not the person you want to grow old with just because you have a physical connection with them, tempting as it may be.

Paula, I think where we diverge is that you’re making a point about judgment which I absolutely agree with. Should we not do something with someone because we fear their judgment? Should we not have sex cause we’re worried what they’ll think of us the next day? Of course not. Should a guy judge a woman for how quickly she has sex with him? Of course not. But my mind doesn’t go to judgment. It goes to outcome.

The outcome that I believe people who come to me want with someone is to build a real connection, create meaning behind the moments they have with a person, and frankly for the sex they have, or the love making they have, to mean something when it happens. By having sex with someone before there’s an emotional connection we run the risk of this act meaning very little–which, by the way, for those of you who have had sex with someone quickly and you still want to be with them, doesn’t change your being able to be with them. You haven’t ruined it because you’ve had sex with them. It just means that in a sense you’re still at square one.

You can’t assume that you have something more with someone simply because you guys have had sex. It doesn’t work like that. You can still be at level one in terms of having to build a connection with that person.

Now, by the way I don’t want to give you the impression that simply waiting creates connection either. Simply because you allow more time to lapse between meeting someone and having sex with them doesn’t mean that by the time you do it you’ll have all this investment and connection. If someone’s been bread crumbing you and sending you a text a week for the last three months I don’t want you to take all those breadcrumbs and build a giant loaf out of it and be like, “Oh no, we do have something because we’ve been talking for three months so we can have sex now.” You can have sex now, but you won’t necessarily have any more than if you’d done it on night two because you haven’t had real connection in the meantime. There is no substitute for actual connection.

So, time doesn’t guarantee connection either. What time does is it just creates space for connection to occur between two people who are actually investing. That’s it.

So look, have sex when you want. You absolutely shouldn’t fear the judgment of somebody else and people shouldn’t be judging you for how quickly you have sex. But be self aware. Do you want it to mean something? If you do want it to mean something give it a minute because the experience will be greater for the moments you’ve shared together prior to that happening. And if you’ve already done it or if you want to have sex with someone tonight and you want a relationship with them tomorrow, great. But don’t think you’re any further ahead because you had sex with them tonight. You still have to wake up tomorrow morning and do all of the same things to build an actual connection.

Let me know your thoughts.

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100 Replies to “When to Have Sex with Him”

  • Great video!

    May I add another perspective. I have just entered back into the dating game- after a long marriage, and find that the opposite would be true…. in that I feel judged for NOT sleeping with the guy.

    I have been called old fashioned, a prude, a tease and many other things…. my challenge is that I look very ‘sexual’ (hourglass figure and pouty lips without actually pouting)…. BECAUSE I am aware of my physicality- I dress down (I cover up and never wear short skirts) and I don’t wear a ton of makeup to accentuate.

    I am struggling to find the balance of being flirtatious without sending tooooo many ‘signals’…. as a person I am very tactile, I know how to smile with my eyes, laugh at jokes and engage a man in conversation, but I am afraid to do it.

    Men have on countless occasions told me that I need to ‘get with the times’….. all I can say is that I don’t feel comfortable bending to their will…. because I need to feel something more cerebral, and not JUST physical. I feel being true to myself is massively important- but lately it seems that it is costing me a potential relationship…. or is it?!
    Hope floats eternal :)

  • Matt, I agree with you 100%.
    I actually do what is sterotyped a guy thing…I lose interest in a guy who tries to fast or I become physical with quickly..it’s like I lose respect for them….but I feel this will not happen when I find the right guy. We will both take the time for the real connection,
    One thing I have observed in my past serious relationships is the men TRIED, they communicated and showed me off to all their friends and family right away. And I find guys who aren’t even interested in that nor anything about my grown children only want one thing….they are unavailable and just want a booty call.
    Keep doing what you’re doing Matt!

  • Hi, Matthew, thank you for your video. The issue of ‘earning’ is true for both genders. In my life I’ve always perceived it like this: if a man wants to sleep with me right after he has met me or the like, I wonder whether he is really meaning ME or whether he just wants to have sex. I think the same is true for many men I know: they might wonder “Does she want to sleep with ME, or it’s just that she wants to have sex and I would be replaceable if another man where there right now?” It all has to do with what making love means to us. It has barely anything to do with gender.

  • I do not think sexual builds a connection. If any, for a woman, she can become emotionally attached after sex…where the man does not and it can lead to problems.
    Work on connection before mudding the water.

  • I have a question but I rather put in a form of an email. Would you be possible to
    Give me some advice?

  • Matthew i totally agree in wat u saying! That Unfortunately happen to me..12 years ago i just wanted a nite of passion he wanted more So i gave in it Was JUST A PHYSICAL ATTRACTION! NO LOVE NO CONNECT IMNOW! GOING THRU A DIVORCE AND IM INLOVE WIRJ ANOTHER AMAZIN PERSON! WE SURE HAD THAT EMOTIONAL CONNECTION! THANK YOU

  • This is so true & great advice. I’m in exactly that situation right now & waiting til I know that connection is right. Tempting as it is but waiting til it’s right.
    Thanks Matt. Love ur advice.

  • I agree however, I feel you left a KEY component out. Because of male biological and anthropological programming to sew their seeds and a cultural acceptance that it’s okay for men to have sex outside of committed relationships, men are more apt to want sex to meet a biological need without any interest in any kind of future relationship. Subsequently, women need to be aware that for the man with whom they are about to have sex, the situation could simply be viewed as a means to an end – a vehicle to get what he needs – without any interest in any kind of relationship beyond that moment. For the same reasons, men are also much more apt than women to have sex with little to no attraction to the other person – in which case the women is a receptacle and nothing more. So, the circumstance could even be that it’s not about “starting from square one” the day after sex as you say, but rather, square zero – with no ability to even have a square one. It’s important for women to understand what they want for themselves first – and if it’s something beyond simply sex, they need to weigh the risk when deciding on sex.

    While these days, women are increasingly having sex to meet their biological needs and there is somewhat more of a cultural acceptance of this (although not anywhere near the acceptance that is afforded to men), women are more often seeking a connection beyond the sexual experience and are therefore more susceptible to being hurt if their male partner is not. This is partly why historically, women have been conditioned to wait.

    So, while our society is moving toward a more equitable culturally acceptable view of noncommittal sex when it comes to both genders, the biology can never change. So it behooves women to be aware of the male biological inclination when they are deciding whether or not sex is right for the situation. This doesn’t mean women should judge all men as only wanting sex – most men are also seeking a connection of some sort. And it doesn’t mean women should never have noncommittal sex just because they want it. It just means women generally have more to think about in order to protect their own interests, feelings and emotions.

  • Ladies. Listen to an old woman. Don’t surrender your power. If you only want sex with Mr Right and he’s not the guy standing in front of you, then don’t do it. If you want to have sex and you won’t be destroyed if he ghosts, then do what you want, Sometimes a good bleep is a good bleep and if nothing comes from it you move on, but don’t try to kid yourself. If you’re honest, sometimes you KNOW it’s not going to end in anything more but you do it anyway hoping it might, like you hoped for a pony at Christmas. How’d that work out? (Been there too, done that too, wished I hadn’t too. Forgave myself )
    There are a lot of men who don’t know what they want. They have the introspection of a brick. The older they are, widowed, divorced, the more bewildered they are. Their loneliness is achingly crippling, and sex is how they want to soothe themselves, The only thing they can allow themselves to feel. Sometimes women are/do the same
    But unicorns are out there. Don’t lose hope. I found one at 68
    You keep trying, but in the meantime, be honest with yourself. Don’t deny yourself but don’t let some schmuck disrespect or manipulate you. YOU have the power to do what YOU want.
    Decide what that is, what the situation warrants, and be in your power. Never capitulate out of fear or lack, that diminishes your power. And girl, no matter how the thing turns out, you’re gonna need it.

  • Don’t mind you using this but please change my name!
    So I’ve been talking to a guy, or texting mostly for months now… at least 3 months, all day, every day. We talk on the phone once in a while, mostly on weekends. I’m still going through a divorce (my ex cheated on me is is long gone), but legally I am allowed to date, according to my lawyer. So this guy lives in Austin and I live in Tampa and we’re finally going to see each other in two weeks. I can tell he’s cautious, he never sends kiss emojis, he’s careful about how much he flirts, but will say something small like “pretty” on a picture I send him. Makes me feel like he’s interested. So should I see what happens when we see each other? Does he want something serious? I do! If we have sex will it ruin everything? He wants me to stay with him, I still don’t know if that’s a smart move on my end. I really like him, and I feel like he does too! Help

  • Matt, I think you are right on. I totally agree in that developing an emotional connection prior to having that physical connection is the better way to handle getting to know someone – if that’s what you truly want. I have fallen into the moment and had sex before a true connection was established, and the relationship(s) fizzle quickly. However, as you alluded, sometimes it’s OK – and living in the moment is good. I am old and totally love to go with the flow. However, if you really think that you want a true connection and that this guy could be the one – control yourself and wait. And, as Matthew also states, let him think he earned it. It will mean much more to both of you.

  • Totally true. I have had sex quickly and found that there was absolutely no connection that I assumed there was b4 having sex. And it fizzled quickly. Then I took the approach and took a step back and said I want to work on a connection first and feel like there is friendship, and respect b4 I have sex. I did this and now I am in a beautiful meaningful relatiinship that I value. Thank you Matthew!

  • Thank you Matthew for this precious topic about sex. I like to have sex so much but its not so easy to just go for it so quickly with the guy who has or is showing interest in you. I would always give it a second thought cause I place a lot of value on it, I feel having sex with someone carries a lot of meaning, and obviously one would like to get sense out of it. I feel that an authentic connection is the Basis of future intimate relationships. While thinking about then whats next, what about tomorrow can never be overlooked upon. Issues of sex are things of the HEART, and I would rather protect myself from lasting PAIN a kind sex relationship for now only, Even I may feel I would like to have sex, I do not find it so easy, I would rather wait and see.

  • It did make sense to me. If i make love with someone I’m going to have to know he cares & invests his time with me and showing me he appreciates me by his actions. I don’t want to have sex for no reason. I want it to be special & with someone I care about & respect also.

  • Sex per se is an act which happens on the physical level. Personally, if I give myself to it, I would be investing my whole heart in it … with him!

    It should be a spontaneous, authentic and an honest reaction, a mutual desire for two people. It then, is no longer an act of having sex, this becomes an act of making love for a couple who feel a deeper connection more than just the physical attraction. It may happen anytime…on the first date or, the the 10th perhaps…because when it happens…it just happens! If it does, it makes the connection more beautiful… and, yeah … a reason to pursue the other!

    If you do it on the first date even before a real connection is being established, there is a greater chance for the budding relationship to fizzle out. Sex doesn’t define anything, it may be a now or, a never thing… without the feeling!

    There may still be men and women out there who really want for the real thing to happen. They just have to keep on searching and not remain recluse, if they so want love, perhaps with great sex into it!!!

    I am excluding myself here simply because I don’t date… haven’t dated for quite a while! I’m just expressing a thought, !

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