Afraid to Ask Where It’s Going? WATCH THIS

When is the appropriate time to ask where a relationship is going?

The truth is, we often don’t feel like we can ask because we’re afraid of the answer. 

In today’s video, I share three perspectives that can shift your mindset when it comes to discussing the future of your relationship, so you can finally break free from fear and build a relationship guided by open communication and shared values.

Discover the 4 Secrets for Escaping Casual Dating Traps.
Claim Your FREE PASS for My Dating With Results Training . . .


I continue to put in this much effort and you just keep putting in more, then all it does is reward the amount of effort that I’m putting in right now.

Before we get into the video, don’t forget to like this video, subscribe to this channel and hit the notification bell so that the next time I release a video, you get notified first and you don’t miss it. I was asked a question: “After four months of seeing someone, is it okay to ask the question, ‘Where is the relationship headed?'” So I thought I’d make a video about this phenomenon of getting months into a situationship with someone and not knowing whether it’s okay to ask what we are doing and where it’s going. The first point I want to make about this is that there is a natural question that anyone listening to a scenario like this will ask, which is: “Why hasn’t it come up already?”

What’s going on that you’re four months in and you still don’t know what it is? It suggests one of two main things could have happened.

The first is that this person doesn’t want anything and therefore is just running it down the road for as long as they can without bringing up the subject and they’re hoping that you won’t bring it up either. Often people are quite skilled at making sure that the conversation doesn’t come up by A, never mentioning it, and B, if you mention it or you hint at the idea that you want something more, they withdraw and go cold. And that almost can be like a way, I’m not even saying this is always conscious, but it’s almost like a punishment for having brought it up. It’s like you brought up the … what’s the Harry Potter, Voldemort, he who shall not be named.

“Where is this going?” Is like Voldemort in the relationship is we don’t talk about where it’s going. And if you do, you’ll get punished. I’m going to withdraw attention. And of course, if we really want somebody and they withdraw their attention because of something we did, the connection the brain makes is don’t do that again. So when that person lets us in again, when a couple of weeks later they start to inch closer, then we feel so rewarded for being quiet about our needs. And we go, “I’m just going to not say that again for a while because I’m back in now and it seems to be happening again. So I’m just going to keep my mouth shut about the whole where is this going thing and enjoy the fact that it’s happening on some level.” And that is how we end up with a dynamic where months in and sometimes even years in, I get people come to me saying, “I don’t know what to do. I don’t know where it’s going,” because they’ve got themselves locked into this fear-based cycle. That’s one possible explanation.

The other possible explanation is we haven’t mentioned it because we’re afraid that it’s going to push someone away. And so it’s not that they absolutely didn’t want a relationship, it’s just that we started dating them, we started sleeping with them, and now a few months in, we’ve given the impression through our lack of communicating what we want, that we’re kind of okay with that, with it not going anywhere and just sleeping together. We’ve somehow put ourselves in the casual category by mistake because we’re not actually good at communicating what we want. So why is it that we’re afraid to communicate what we want? Well, there’s a fear that if we actually ask for a relationship or if we tell someone that it has to go somewhere or I am leaving, that we will lose this person. And so rather than take that risk, what a lot of people do is they just give more effort to the situation thinking that if I give more effort, it will equal progress in the relationship.

Eventually I’ll become indispensable to this person. Eventually I’ll be bringing so much value to their life that there’s no way they would want to turn back. And so we don’t ever name what this thing is, we just keep giving more to it. And what we don’t realize, and this is the first big thing I want to give you today, I want to give you three different things to think about on this subject that are going to help you and help change the way you approach every dating scenario from now on as it begins to progress.

The first thing I want to say is effort does not necessarily equal progress, and past a certain point where we’re not communicating what we want, effort absolutely doesn’t equal progress. It equals permanence. Permanence in the dynamic, reinforcement of the amount of effort this person is putting in right now. Because if what they learn is that: “I continue to put in this much effort and you just keep putting in more, then all it does is reward the amount of effort that I’m putting in right now.”

And often what happens is even worse than that. It’s when someone’s putting in this much effort and you keep putting in more and more and more, they may even see what happens if they put in this much effort. And if you’re anxious, if you’re anxiously attached, when you feel them withdraw, you put in even more effort. And they go, “Oh, okay, so I can put in this much effort and I get even more.” And this isn’t necessarily a conscious thing from a bad person. There’s an element of it that’s human nature. What’s the least amount of effort I can put in for the maximum reward? So now you put in more and they put in less and they put in even less and you put in more because you’re even more afraid of losing them. And that’s how you end up in a situation where you’re giving so much and they’re giving so little and somehow it just keeps going.

You say, “Why don’t they just let me go if they don’t want me?” And you want to say, “Well, they’re not letting you go because they’re giving this much effort for this much reward. So why would they fully let you go?” More effort does not equal more progress. More effort equals permanence of the dynamic you don’t want.

Number two, we have to lose our scarcity mindset around this person. One of the reasons that we accept bad treatment from someone or we just accept stagnation where it doesn’t go anywhere is because we’re afraid we’ll never meet anyone like them again, but we will. There are great people around. This isn’t the only person who’s going to like you. This isn’t the only attractive person in the world. What we have to start telling ourselves is that this person isn’t the irreplaceable thing in this equation. My time is the irreplaceable thing in this equation.

So I have to start being more afraid of losing my time than of losing this person. The individual who asked me this question about after four months, is it okay to ask where this is going? The answer is of course, because it’s been four months. Four months is a significant chunk of time that cannot be got back. So this person I know is more afraid of losing the person than they are losing their time. We have to flip that and say, “I’m going to change my scarcity mindset. I’m no longer going to have scarcity around this person. I’m going to have scarcity around my time and say I’m more afraid of losing my time than losing the person.” When that’s the case, you’ll no longer operate out of fear of losing a person. You’ll operate out of fear of losing your time.

Number three, while we have to be quicker to decide whether something is going anywhere or progressing, we have to be slower to decide that someone is the one for us.

What happens when we like someone is that we just decide that this is the one. This is my person. And once we’ve decided that, we will ignore any evidence that we could be wasting our time here, that this thing isn’t moving in the right direction because we’ve already decided they’re the one. So the only question we’re asking is how do I get them? But when people say this to me, I had someone say this to me recently, “Matt, I know he’s the one, but I just don’t know yet if he can meet my needs.” And I said, “That’s an oxymoron. These two things are a contradiction. You can’t say they’re the one and say I don’t know if they can meet my needs in the same sentence because the person who is the one for you is the person who can meet your needs. Finding out whether they can meet your needs comes first before you decide someone is your person.” So this brings me back to the original argument. If four months in you’re asking, where is this going? Is it okay to ask him?

You have to tell yourself that the only way you’ll know if this is your person is if you have that conversation. And if you have that conversation and the answer is, “No, I don’t want more than this,” then they can’t be your person because they can’t make you happy because you being happy means being with someone who chooses you. If they say, “Oh, I absolutely want to be in a relationship with you. I want this to go somewhere. This is an amazing thing we have.” If someone says that, then you can say, “Oh, it seems like this is my person because they’re in in the same way that I’m in.” So many of us are so afraid to lose something that’s not the right thing in the first place, and we have to lose that fear. We have to switch the dialogue in our minds from, “I know they’re the one, but I just want to get more of my needs met by them” to, “Until I get more of my needs met by them, they can’t be the one.”

And in the context of today’s question, getting your needs met means being honest about the fact that unless this relationship is going somewhere, you can’t invest any more of your energy into it. And by the way, as we’re going through this video, I want you to understand that I may talk for a few minutes on this subject here, but I always know that it brings up bigger questions. It brings up more nuanced questions. Matt, what you’re talking about is communicating for progress in dating, but what does that look like after date one, what does that look like after the first two weeks? How do I stop it from getting to four months and I don’t know where it’s going? Or if I am at the four month mark and I still don’t know what it is, how do I actually have that conversation? All of these questions are the kinds of questions that I answer in a live training I did called Dating With Results.

That is my most popular free training program of all time. It is for people who want to be intentional about their love lives, who want to stop wasting time, and who actually above all else know that the thing that would make the biggest difference to their lives today is finding love in the form of a deep and meaningful and committed relationship. And this is what I teach in this training. It’s practical, it’s insightful. It will change your dating life forever. Go to to register for free and just make sure that you watch it in the next 48 hours while you have your pass. Let me know what you think of that training once you’ve been through it. I know you’re going to find it incredibly valuable, and I’ll see you on the other side.

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10 Replies to “Afraid to Ask Where It’s Going? WATCH THIS”

  • So, Matt: when is the appropriate time to ask where is it going?
    Do you have a concrete time – in terms of no of dates, time passed or feeling of the situation?

    Because I can tell you this: I met a guy online. He lives in Dublin and I live near London. So I thought it would be a waste of time but bis messages were so nice that I answered anyway but was writing to/dating other people (Is that mean?). My other date (x) wanted to be exclusive and I reluctantly stopped writing to the Dublin guy. But after a couple of dates things with x disintegrated and I found myself relieved. So Dublin guy came to London and said he could come to my town to see me. We had to really nice dates. I happen to go to a conference in Dublin in 2 weeks. I had planned that last year. So I’ll spend a couple of extra days to explore and it would be a nice chance to see him again. He now invited me to stay with him and I’m slowly accepting. Als if things go well, I kind of want to ask him. Because what’s the point in investing and getting attached if I don’t even know if/when I will see him again? So when/how do I go about this?

    1. Ooh girl that’s a hard one. I’d be afraid that if you only seen him twice that maybe it might be too early to ask? That is unless you talk a lot on the phone? Can you give us more of a backstory? How much you’ve seen him and for how long?

  • What if you meet someone and they have a lot of good qualities, but there are a few that are very hard to deal with and you don’t want to change them. The guy that I am dating talks this baby talk that drives me crazy. I have said something to him nonchalantly, but he keeps doing it. He also has a big dog that like to sleep in the bed with him and I am allergic. I feel I should hit the next!!

      1. Say something before you build up resentment then there’s no turning back. If it were me, I’d take a Zyrtec allergy Med and kill the baby talk!! There’s nothing worse than hearing “baby talk” come from anywhere but a crib!!!

    1. Girlfriend. You got to speak up on those two. You will soon start to resent him. Who knows, he may be very understanding and accommodating. But if you’ve already built up resentment there’s no turning back.
      On the other hand, he SHOULd be accommodations and gentleman like. Although I have dogs and love furry friends, BUT it is a human’s bed and humans deserve first dibs! Don’t hit him right away with both. Start with the most annoying first! Your health is most important tho!
      If it were me, I’d probably take a Zyrtec and then go after the baby talk since that’s a BIG turn-off for me!

  • Adri – You might consider expressing what you need and asking him if it would be willing to consider accommodating you. Hinting is pointless with men. E direct and clear. “I’m allergic to dogs and can’t sleep at night with your dog in the bed. Would you consider having him sleep in a different room?”

    The same with the baby talk. Here’s why. You expressing your needs explicitly, clearly and directly = providing a blueprint for him regarding how to make the relationship work really well for you.

    If you don’t express your needs, your hiding from him the path towards making a great relationship with you possible.

    When you reveal the path, he may or may not take it. However, at that point you’ve done your part by making the path known to him.

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