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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”

  • When deciding whether to become physically intimate with someone, the answer really is a personal individual choice as you so eloquently explained. I know myself enough not to do it quickly without knowing the person well enough and truly knowing what the man’s intentions are before doing so. Once I feel a deep connection, feel safe and he has proven to me that this isn’t a fling then I move forward. But this is where I am in my life now. I’m a 45 yo divorcee with 2 daughters so I’m well aware of who I am and what I want and what I won’t tolerate. In my 20s it was completely different. I didn’t know who I was or what I wanted so I didn’t care. Everyone is at a certain point in their relationship journey so there isn’t a cookie cutter answer. Ultimately you need to decide what you want at that moment in time.

  • I am trying to buy tickets to this live event in Houston and am in your bio that I clicked on from instagram….there is nothing for me to buy tickets. Please help me.

  • I enjoyed this video, it gave me something to really think about. I am currently talking with a guy who I have things in common with. We had recently talked about when we’d both feel comfortable having sex. I told him that I’d prefer to wait until I felt ready and he was understanding of this. We both feel like there should be a mutual connection (more of an emotional one I guess) before we become intimation a physical level.

    One of my biggest fears for sex isn’t finding the emotional connection or finding the right guy, but more or less what he is going to think of me that first time. I am a very self-conscious person, so it’s hard for me to find someone who is going to still be understanding of why I might be self-conscious. It definitely has taken its tolls on me since I was very young.

  • This ties in with the “Where are we in a relationship” question. Make a connection with someone first. Find out their values, what they are looking for in a relationship, where they see themselves in the future and what that relationship might look like. Then you really know if this is someone you want in your life for the long term. Once you know those things, then consider having sex and moving forward. I have never asked a guy the relationship question, because I already knew we were looking for the same thing before I slept with him. Those relationships may not have worked out but I never had to question if he was my boyfriend.

  • Dear Matthew,
    What a great topic !
    As a french citizen, sex is part of our conversations all the time in my country.
    I even believe that sex is the cement of 2 persons who are in love, all their life.
    In the seduction process, there is a big part of sensuality, physical connection before even getting to know the other one very well intellectually.
    I feel attracted by a great personnality and a conversation with a man if i can fantasm myself in his arms. No matter how soon we have sex together. If sex is not good, i can not be with him anyway after. Sorry if i seem very pragmatic.
    Thanks again for your great work. I love it all.
    Cheers from south of France:

  • Great video and insight. Always a question as to when is the right time. I think you just know when it’s okay. Thx for your videos. Love them

  • Hi Matthew and All,

    Thank you as always for your insightful words :)

    My dilemma is this: After having tried online dating for over a year and pretty much all the various dating sites what I have found for the most part is this: that most men seem to have a sense of entitlement when it comes to sex; as if it’s somehow a “given” because, for example, in my most recent dating experience, I had been seeing someone regularly for about two months. I told him at the outset that I don’t engage in casual sex (but do not judge others who do) and I asked him if he was okay with that and could be patient; he assured me that he could

    And for about two months he was a perfect boyfriend in all ways.

    Except that he began to pressure me about sex and asked me “What’s it going to take? Our 10th wedding anniversary?” I explained to him that we would need to be tested for STD’s as a matter of course and he then replied: “You’re just putting up more obstacles” – to me it didn’t seem that unusual at all.

    My point is that I am really starting to feel that I was born in the wrong century or something as I am very much a Romantic and I feel that, for the most part, men today only seem to want sex.

    There’s nothing inherently wrong with that in and of itself but for a woman who values both love and authenticity, what am I (and others like myself) to do? Because I honestly don’t know.

    This most recent experience, I was made to feel “difficult” and “strange” because according to this man “I’ve never met anyone that had me wait 2 months to have sex” and my response to him “Well, I guess now you have met someone who will make you wait 2 months to have sex” and we effectively ended our relationship.

    I guess I’m just really confused about what men want.

    I never wanted to become a bitter and cynical person because I know there are good decent and kind men out there but for the most part, at least in my experience, I am thinking those good decent and kind men are either “taken” (by marriage or long term commitment) and the men that remain are just not worth my time.

    I would like to ask the other respondents on here (both men and women) how they approach this in modern dating as I am starting to feel that I belong in a Jane Austen novel or something ;)

  • This resonates SOOOO much (like pretty much everything else Matthew says). I really appreciate the sex-positive + connection-oriented approach, and loved hearing that he would give the same advice to men (it truly does work both ways).

  • Hi Matthew

    I have really enjoyed your videos and advice (from Australia). This one I found particularly interesting.

    I am 55…just. And for me, it is the attraction, the intellect, followed by the sexual connection. A person needs to appeal to me on many levels before we can connect sexually, and then it becomes the most wonderful experience.

    It seems that guys on dating sites have their own ideas, and first date is a coffee or meet and greet date, if they like what they see, they try to get the second date in the bedroom, and it is just about getting laid.

    And it is hard to find someone you are attracted to that wants to just be with you and get to know you, on that other level, and to build on a relationship, or build that connection.

    For me, if I find the conversation lacking or shallow, I move on very quickly. But it is certainly very frustrating.

    Sometimes it can happen extremely quickly, and I think it is about the two people involved, and where they are emotionally at a given time.

  • I totally agree. Time is relative, for me there needs to be a deep emotional connection and this takes as long as it takes. So many factors are in play here, how you first connected, in person/on line. How often have you spoken (I mean actually physical conversation not ‘text chat’), are your values aligned etc. So no I wouldn’t have sex with a guy on a first date if I met him online the day before but I might if we had been chatting on the phone for 3 hours a day, texting and exchanging picturesfor the past month and this was the first opportunity we had of actually meeting in person.

  • Matt is absolutely right. Most of important stories don’t start from sex and all the male friends that I know say to me they don’t really like women who give them away so quickly.

  • Matthew you are absolutely spot on. The dating, the messaging the build up is the foreplay! Why miss out on this, the most intimate stage of a relationship. Sex is no where as intimate, as having a connection and is more intense, lustful and fun. The best sex is always about the connection. Thank you Matthew for articulating this perfectly x

  • Matthew,

    For so long, I have held the misguided belief that sex leads to a relationship. I felt that if I man wanted to go to bed with me, he must have feelings for me on some level. Unfortunately, I now know that is not that case. Watching your video, however, clearly communicated what I have slowly realized through trial and error. It would be nice to get your advice on signs that two individuals are building a connection with each other. Maybe you’ve already posted something about this already. Whatever the case, I would love your feedback.

  • How is it possible ? I thought we were building a real connection. After doing so many things together for months, then after enjoying sex, only to have him grow cold and want to be “friends”. We had a disagreement ( one) and I was disappointed that he didn’t follow through on plans we had made. He said I was a “drama queen”, and wouldn’t have any more discussion. He said he couldn’t be a “boyfriend” to me.

  • Ok Matthew so all of that begs another question! What IS, or how do we know, what a real connection looks or feels like?
    Is having your hair ruffled mean theres a connection? Being asked what we want to do for dinner? Having your Plumbing fixed? Your children being asked after? Or do you mean being actually told you mean something.. … mmmmmm hard to know as i havent had a ‘relationship’ other than LIVING with my ex husband for 30 yrs and thats a different kind of connection……. xxx

  • Thanks for your video! It cements the idea I was thinking about regarding waiting until sex. I’m sick of thinking I’ve got a sort of connection with a guy via messaging, then meet and usually ends up with bad meaningless sex. Then more often than not they disappear, or it was so awful i dont want to see them again. I feel it’s a vicious circle. I miss that connection you were talking about . So now I’m going to build a proper connection first and see if that works! I need to respect myself more so they do… if that makes sense? Wish me luck! Forever hopeful….

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