Want More Than a Situationship? DON’T CHASE, Do This Instead

How soon is too soon to sleep with someone?

I wish there were an easy answer, but this is definitely one question that isn’t “one size fits all.” In today’s brand-new video, I show you how to explore what that looks like for YOU so you’ll be ready to act (or not act) the next time you’re in that situation.

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Current Dating Situation . . .


This month I had a question from one of my LoveLife Club members who asked whether it was advisable to sleep with a guy after a second date. Now, she did also caveat this by saying, “I am coming off the back of two years in a friends-with-benefits situation that I don’t want to repeat.” So here’s what I hear in this. I hear someone who has slipped into a dynamic with someone where she’s sleeping with him regularly or every time they see each other at least, but it’s not progressing and that’s probably a dynamic that she ignored very early on in that situation. And I also hear someone who is looking for something serious in her life. She wants a real relationship where she can be intentional.

Now, I think sometimes the argument of “Can you sleep with someone on a first date or a second date?” quickly becomes this almost political, gendered thing that becomes quite a misnomer. Hopefully, all of us here in this particular space can agree that it doesn’t matter from the point of view of “Can you? Is it okay to?” whether you sleep with someone after one drink or six months? I don’t have an opinion on that other than of course it’s okay. The question is, “Does it serve you and does it serve the path that you want to be on?”

Now, I just said that what I picked up from this question is that this person is being intentional about wanting to find a relationship. So what we have to do then is ask ourselves, “Is what I’m doing the behavior of someone who is being intentional? Does that communicate to someone else and to myself that I’m being intentional?”

I recently was in my local coffee shop and there was a guy in there in his mid-20s, really lovely guy who recognized me and started speaking to me. He started telling me about this person that he’s dating and how, because he really likes her, even though inside there’s all these feelings he has about this person and I’m paraphrasing what he said to me here, but he essentially said, “I might want to scream, ‘I love you, be with me forever.'” But given that he really likes this person, he was evolved enough to say, “I don’t think it’s a good idea for me to do that. Instead, I’m going to go at an organic pace with this person to see what it could actually be.”

Now, that brings up an interesting distinction, doesn’t it? There’s what we feel like doing and there’s the behavior that actually serves us in our intentions. For him his intention was to have a relationship with this woman that he was seeing. So suddenly telling her, “I love you, and oh my God, I just want to be with you all the time,” and doing all of these things. If it communicates an intensity that would no longer feel organic might it might actually disrupt this thing that they have together. It might not if you get two really intense people together and they love saying all these things to each other, then it can be quite fun. But it can also lead to an inorganic pace.

What is a love bomber? When we talk about love bombing and the danger of love bombers and some of you have been in a situation where you feel like you’ve met a love bomber, someone who showered you with praise and grandiosity and statements about the future and about how into you they were and they’ve never felt like this before and drop everything and take a trip with me. The love bomber is really someone who has minimum intentions disguised as maximum intentions because all of that grandiosity seems like all the intention in the world, but actually there’s very little substance behind it. The love bomber is just indulging their feelings without any regard for the consequences of how that might feel to somebody else or how much it might hurt them when they’re not able to back it up. It has no regard for, are we at the same level here? Do we have the same intentions here?

I actually believe that you can look at sex through the same lens of intentionality. You may have someone that you’ve been on a couple of dates with and you feel really excited about this person and from a sexual perspective you feel really turned on by this person. So the combination of, “I like you, I feel connected to you and I am sexually really drawn to you and I’m horny.” That combination of things at the end of a second date might have you saying to yourself, “What I feel like doing is going home with this person.” So your feelings are telling you, “Yeah, absolutely go do that thing.” And there’ll be some people that say, “If it feels good, do it.” But we know we don’t apply that to everything in life. It would be really bad if we said, “If it feels good to punch that person who’s just wound you up in the coffee shop, do it.” We don’t say that about that thing, so we should be careful of just applying that to romance. People do that with romance, don’t they? “If it feels good, just do it. Just enjoy yourself.”

But we have to ask ourselves, what serves the path I want to be on? If I’ve been on two dates with someone and I like this person and I want to see where it could go, then actually the most important thing on my mind right now is not jumping into bed with them. The most important thing on my mind is, “Is there actually some compatibility between me and this person? Does this person have the same intentions as me in terms of what they’re looking for in their life right now? Are they on a similar path? Are we in alignment in what the two of us are looking for in life or the way that we think?” And if we start to bring compatibility forward and we recognize that, “Okay, by the way, it’s a great thing that I’m attracted to this person that’s really wonderful,” but that ultimately is not going to be the deciding factor in whether this works. It’s, “Is there a level of compatibility that I can find with this person?”

And if I show that person that I like that what’s more important to me than rushing to go home with them is to get to know each other on a compatibility level and to assess whether we’re on the same page about what we’re looking for, then I’m communicating my intentionality. I’m actually making that clear to someone. And if I’m making clear my intentionality, then there’s a much higher chance that that person will take me seriously. I want to be clear about this because I don’t want anyone watching this video to think that this is coming from a prude or this is coming from someone who’s got some tilt in a religious direction of waiting or I don’t have any of that. I totally understand the urge to rush home with someone because you are attracted to them, and this isn’t some sort of prudish, “No, you should wait because you shouldn’t give that up to somebody too soon.”

It’s more me saying, when we’re at a stage of our life where we know that the game isn’t, let me just get my short-term needs met, the game is let me actually see if I can find a person I can build with. Showing someone that the most important thing to us is not the euphoric high, be it sexual or otherwise of early dating, but instead a sort of honest assessment and pace in regards to what we actually have or don’t have together, that’s the most important thing to me because that’s what I’m looking for. And it should be said that our perspective there, our clarity there can quite quickly be muddied by sex because then we can feel a bit closer to someone than we really are. Then we can have the highs of that that are very distracting and an escape from reality.

We can find ourselves in a situation where all of a sudden there’s strange emotions like this person, if they now don’t call me, I feel used, and that now brings this sort of strange entitlement dynamic into the situation. Instead of just being able to organically see where it’s going, I’m now thinking, if it doesn’t go anywhere, I’m going to feel used or I’m going to feel like there’s something wrong with me. It’s really going to, I’m gonna feel shame that I did that. Those are all more ways that we complicate a situation that we don’t even know is right for us by just acting on our feelings too soon.

So don’t see sex as a special category of things, necessarily. See it the same way you would any other thing that is important to you, your time, your energy, the kind of statements you make to someone, the kind of promises you make. What we feel like doing . . . And we all know what we feel like doing when we’ve had a great date, we feel like marrying them immediately. But what we feel like doing has to be separated from what serves the path we want to be on. If you want to be on a path to a real relationship, to a life of building with somebody, then your ultimate priority right now is not acting on feelings. Your biggest priority is assessing whether you have a viable builder that you should be investing more time in.

If you enjoyed this video and you want to continue the journey with me beyond this video, I have a free tool on my website at YourDatingSolution.com where you can input your dating challenge right now and it will recommend the best of my solutions from the last 10 years to help you with what you are going through. Go check it out at YourDatingSolution.com and I’ll see you over there.

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4 Replies to “Want More Than a Situationship? DON’T CHASE, Do This Instead”

  • Great advice, as usual. I understand your advice doesn’t come from a religious stance, and I personally think religion sucks. But I do absolutely trust God’s ways, and it’s for many of the same reasons that you listed why He asks us to wait for marriage. It’s not about “rules”, it’s about protecting His children. If you don’t know Him, I HIGHLY recommend it!!
    P.S.: I am also not a prude, and did not wait until marriage to have sex…but wouldn’t it be a beautiful thing?

  • Hi Matthew, I really appreciate your videos and overall knowledge. You are an amazing mentor for all that you contribute to the female persuasion,insert smiley face. I just wanted to weigh in and mention, and I hope you agree even in part, that the whole dynamic of the timing issue of when to take it to that final level comes down to 2 things. Again,just my opinion. Does he see her as the exception or the rule. If it happens 2 dates in and is the latter, bye bye birdy. But it’s the former, it won’t matter, will it. I have always found this part of the male thinking to be an enigma to say the least. Does he decide right away, after a few mins of getting to know you convo or when. I feel this is a major if not a definitive factor in how that will play out in short or long term. Thanks for reading.

  • Hello Matt!
    I truly enjoy watching your videos and following your advice on relationships. I think he has helped me in so much. I only wish I would have found you just a tad sooner than I did. Let me explain… this comment goes towards those that tend to be “love bombers.” Although I feel like you are correct for the most part on your assessment of them, I do think there are instances where that isn’t the case. I say that because after hearing your definition of one, I realized that I fell under that name recently. With that being said, trust me, I regret letting my emotions take over and allowing my mouth ti blurt things out. I am not in my relationship with minimal intentions in mind. I genuinely want to see if we can make it long term permanent. After watching several of your videos, I have been working on myself to change those areas and get better control over my emotions. I just hope I am not too. I have a tendency to wear my heart on my sleeve. Not always the best trait to have. Any suggestions on how I might correct any damage that I may have caused? Or do I just lay low and see what happens? I truly want to make this a lasting relationship with the man I am seeing!

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