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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”

  • Hi Matthew!

    I watched the video learning a lot of things but one thing I still don’t get is, how would you define connection?

    In your video you’ve mentioned different kinds of connection – physical, intellectual, value-wise. What type of connection do you think is crucial for a long-term, committed relationship, and in how do you see that connection happening?

    Thanks a lot for your informative videos! I look forward to them every week.

  • These guys who judge you for sleeping with them too fast, saying that you are easy and not girlfriend material and so on, after they do have sex with you, they are hypocrites,they are just as easy then, it’s no different, why would nobody call the guy easy?
    I think sex with someone is way better when you have a connection already, however, it does build a deeper existing connection.

    Matthew you are awesome!I have been following you for years:)

  • Connection definitely makes sex better however you can have sex straight away and still have great sex. I feel it’s just where your head is at in the moment. If you just want sex great if your looking for a connection sex quickly will probably just leave you wanting more and unfulfilled

  • I realised over a period of time that male and female brain wiring is different….and almost all men want sex on the first date in india…and some ask for it directly so you know that they are not the ones you are looking for but some sugarcoat their desires and pretend that they also are looking for a connection and then manipulate you to have sex in the end….am so tired of this same series of events and conversations…and get so confused coz when next day they disappear-I feel like shit…so now I go with this shield and prejudgements -which I actually dont want to have ….coz those are hurdles in building a genuine connection with genuine people…this video did throw a bit of light on what to do…but still it remains a question -because guys are sweet and attentive and understanding and wise till they have sex…and then they go cold the next day and reappear when they want to have sex again…I still wonder if am meeting all the wrong people..

  • Hi Matthew, how are you? I really enjoyed your video, and it actually came at a perfect time. Normally I would say that a woman should not be shamed about wanting to have sex with someone early on, men do it all the time. I usually can have be intimate with someone because I’m attracted to them or just want to feel the physical closeness. However, I just recently went on one date with a guy and I know he is very attracted to me As we sat in the restaurant I was enjoying his company and began feeling like I wanted more than just sex with him. I remember I took my napkin and wiped off some of his food from his mouth, and I never feel like that right away. Anyhow what I’m trying to say is I know that he wants sex from me, however I feel like I want to wait because I want more than a sexual relationship. I feel that things have cooled down between us. I have shared with him that I enjoyed his company and told him straight out that I need more than sex. That I needed a connection. He hasn’t totally let me go and did say that he understood but I know he still wants it soon. So I de used to take a pause , and not text as much. I don’t want to appear too desperate nor do I want to feel that I have to submit in fear of losing him. So he still reaches out to me and appears to still be interested. We were planning on a second date but he informed me that it all depends on if he has to work on a prior commitment he had. But said definitely the following week. So what I am trying to say is normally I act like a guy meaning having sex with someone early on is okay for me with no shame attached. However now that I find myself attracted to this guy ( as I feel myself wanting a true relationship
    With him) I don’t think sleeping with him right away is smart of me. I feel that it might ruin my chances. So I do agree with all that you said on your video.
    But tell me
    Matt what do you think the rule of thumb is as far as waiting? Yes, I know that it’s different for different people. But what do you think . Three, four,
    five or more dates in??? I’m curious! I enjoy all your videos and advise! Thanks Matt. If you have the time I would love to hear a response from you. Take care!- Susann

  • Thanks for this, I really needed this, I have had sex with a guy I just met hoping it would facilitate our connection, only to realize, we re still at stage zero, we re still trying though, but it’s okay.
    Kate

  • Hi Matt, My LDR with my beau we spent 3 1/2 months bonding via phone. We had an amazing 3 day date. He had us schedule monthly visits (dates) after 3 days together. Both of us rushed sex and recognize it was a bit to fast for both of us but we still speak almost daily with a minimum of hour long conversations. Now he’s scheduling a week long date with me. Do I back off the sex part or continue to have it. We both talk as if its exclusive and long term. He wants to meet my friends and family. We have amazing chemistry. Just realized we rushed it but we still long to be together. He jokes about prenup but says there’s usually a ring of truth in what he jokes about and he says he wants to get married again. I have a huge calming effect on him and we miss each other. He’s not into PDA but amazing when its just us. What do I do? Have sex again or don’t?

  • OK . That’s official, you’re a genius ! :)
    lovvvve your smart and enjoyable videos. They always put things in place, even if we already know some of the things, you make them so clear and accurate !
    well done and thank you as always

  • I wonder, what do you say about a relationship that starts when there is attraction but not passion…can this work ? can you fall in love with no passion? Does physical warmth and passion influence the passion for the relationship..?

  • Thanks Mathew you have just highlighted on a lot of questions that I have been having for the last three years.i have been sleeping with the same person for the past 3 years but yet don’t feel any sense of connection besides the sexual one. I ask myself if it’s because we had sex too early or its just not ment to be. The worst part about this entire thing is not being able to move on with other people.

  • What you said is so true I have experienced this in my last relationship. Thanks for this advice Matthew

  • Hi Mathew,

    Interesting & intriguing worthy video, covering some rather salient points on when to have sex with a guy.

    I know it’s an extremely personal decision with no “one size fits all” option (no pun intended).

    However, for me, I feel it’s the “connection” that is the deciding factor when to choose to sleep with a guy. Even if I’m attracted & want to have sex with a prospective partner, or turned on enough to want sex with him in the moment, I don’t.
    And it is not about delayed gratification, morality, or making him earn it. It’s more significant and important than that.
    For me, sex without a connection feels bad.
    I have learned that no sex is way preferable than bad sex.
    So I choose to have sex only when I connect with someone. I don’t have sex to try build a connection.
    I have connected instantly & had great sex on the first night which led to short but also to lasting relationships, both without regret.
    In essence I’m saying that for me, the connection & when it happens spontaneously ignites my choice to sleep with someone, not having sex to help forge a connection.

  • I really enjoyed that video. Reading some of the comments from women, they had sex on the first night because of impetuous emotions, and I’m assuming they were quite young. The comment from the man about buying a car and eating out was typical of what many men use to rationalize having sex quick into a relationship.. Had nothing to do with feelings or wanting a genuine relationship (ladies, paying attention?). I think some people think that having sex without hesitation is a thing that makes you more modern, more elevated. But being much older (and quite liberated) I can tell you are either giving in to your gut desire to have sex (wouldn’t matter all that much who it was) or you suffer from low self esteem and feel required to go along with it. Using thought and restraint when it comes to sex is a marker of emotional intelligence and maturity. Nothing wrong as you say having sex when you want, but what is the real outcome you want, because I have never known anyone who got the outcome they wanted just because they had sex.

  • Well said
    Thank you for always sharing ever since I follow Matthew im leaning new things daily keep it up the good work

  • Being newly single later in life I try to heed the advice I gave my own kids as they were starting to date in a serious way. If you can’t look someone in the eye and have a conversation about sex you’re probably not ready to have it. Great sex usually requires communication and that requires some connection. Sex in a relationship can take a well built connection with someone through the roof. So if you are trying to build a meaningful relationship at least wait long enough to have given it some thought and had a conversation to express what you are feeling and what you are looking for. Having a connection, feeling comfortable and trusting make sex, for me, soooo much better.
    Thanks for the videos. I always learn a lot from you Matthew!

  • Thank you! I have been struggling with this subject lately. You cleared up the confusion and identified some insecurities that have been arising.
    Cheers,
    Vicky

  • What’s not being addressed here is “is it smart to have sex with someone you don’t know well?“ The answer is no. You have no idea who this person is unless you’ve spent time with him. Media is filled with horror stories these days of women who have connected with predators. I’ve had a few close calls myself and I thank God I chose not to be physical with them. I love sex. But I want a safe partner. And that comes with taking your time to get to know them.

  • Matty ,
    Thank you very much I really needed this message I got from your video I enjoyed and well digested and you really answered what I have been battling with in my mind. Reason I finally got into a relationship just in a week he is demanding for or rather to him he calls just romance. Now either of two am not comfortable with because what I needed is the connection first not physical desire that will not just last and that create fear in me course i like him but want to build and if not so am about telling him off!.

    Tnx Katie

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