Scared It Won’t Work Out? Use These 5 Questions to Know . . .

We’re told that when we’re with the right person, we’ll feel certain. But what if instead of a “hell yes!” or “hell no!” what we’re feeling is more of a “well, maybe . . .”?

If you’re in this position, I hope you’ll join me for today’s new video, where I share 5 questions you can ask yourself to get more clarity and approach this situation from a place of introspection rather than panic.

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When you know, you know.

Pusha T:

If you know, you know.


This is a phrase that’s thrown around a lot in our love lives, this idea that when you’re sure about someone, you are sure. You don’t need to ask any questions, you don’t need to ask anyone else’s opinion, you don’t have any doubts, you just know. I think that this is a very destructive idea when people are looking for love. I’ve also heard in self-development communities the idea that it’s either a hell yes or a hell no.

And when we apply these things to our love life, it can leave us feeling like we are somehow inadequate because we’re not achieving that feeling with people. We hear stories of people who say, it wasn’t even a question. Once I knew, I was all in. It’s absolutely true that there are people that get that feeling and that is what propels them into a long-term relationship or a marriage. But that’s not necessarily true for everybody.

And I think one of the most pernicious ways of thinking, when it comes to our love life, is that there is this one-size-fits-all for how everyone should get into a relationship. But that assumes that we are all built the same. Some people are built for a level of certainty. When they feel something’s right, they just go for it. Of course, they’re going to have an easier time with that feeling of when you know, you know.

But other people aren’t necessarily built that way. They’re built to be much slower to make really big decisions in their lives. They’re built to analyze far more. They’re built to doubt their own judgment much more than that. There are people who struggle with their own anxiety and their decision-making. They’ve learned not to trust themselves or their feelings, or they’ve got it wrong so many times that they don’t even know what the right feeling is anymore.

A big problem with the “when-you-know-you-know” philosophy is that it assumes we’re all built the same in the way that we fall in love. The other big problem with it is that there’s almost an arrogance to that statement. Because when we say, when you know, you know, it always carries this implication that when we don’t know, it’s because there’s something wrong with the other person. It’s always their fault.

It’s always a way that they’re deficient, that they’re lacking, that they don’t quite live up to the promise of what we are looking for, and that’s why we’ve never been able to be sure. It never makes us the common denominator. It would be more accurate for a lot of us to say, “When you don’t know, it might be to do with them, it also might be you, let’s explore it more.” It’s less sexy than saying, “When you know, you know,” but that’s the truth.

What I thought I’d do in this video is hopefully, just even between me starting this video and now, it’s been a bit of a pressure valve for you in thinking, oh, you know what, I don’t have to constantly run from everything when I don’t feel 100% sure. But I now want to give you some ways of having this conversation with yourself. When you find yourself in a place of confusion about someone, what questions can you ask yourself or what model of thinking can you use to try to explore whether you should persist with it or whether you should listen to your doubts and go looking for another person?

Number one: Do they make me a better version of myself? This is a really important question because there are people we can feel wildly attracted to, but they make us a worse version of ourselves. We feel insecure around them all the time. We feel anxious. They make us a meaner version of ourselves. They make us a version of ourselves that’s less interested in our own life. We don’t feel supported by them. We feel unsure of ourselves all the time.

But there are other people who, though we may be wondering if they’re the right person, make us feel like we are a wonderful version of ourselves when we are with them. We’re kinder, we feel more at peace, we are more vulnerable, we’re more confident. So, “Are you a better version of yourself by being with them?”

Second question:  Do I feel more of myself when I’m around them? This is similar, but subtly different. Because there are some people that by the way that they handle us, the way that they encourage us to talk about ourselves, the way that they make us feel comfortable about what are normally hidden parts of ourselves, we actually start to feel like we can be more of ourselves. We can really open up, we feel accepted by the way that they treat us, and so we actually start to become more of who we really are.

We’ve all had that situation in the past, haven’t we, where there’s been someone that we are really trying to get because we think they have some kind of value. We think they’re important, they’re impressive, they’re super charismatic, there’s something very attractive about them. And we go into this mode of trying to impress them, trying to win them over.

And in the process we become less of ourselves. We start to hide the parts of ourselves we feel ashamed of or nervous won’t be accepted, the parts that make us geeky or a bit weird inside, the parts that we think make us less cool. We start to shut ourselves down a little bit and only let them see things that we think they will be impressed by. This is a version of not being accepted by someone. When we find someone that naturally makes us want to just show more of ourselves, be more of ourselves and feel safe to do all of that, that’s a pretty beautiful sign.

Number three: Am I growing by being with this person? I think one of the most beautiful things about a relationship is that there is that genuine 1 + 1 = 3 synergy. You find someone who, by being with them, your world expands, you learn. They are good at things that you are not good at. They’ve built skill sets in their life that you don’t have. And by doing that, we actually expand by being with them. I feel like, oh, I’m learning. I’m growing. My identity is expanded and enriched by being with someone like you.

And that person might be different from the person we expected ourselves to be with originally, especially when we’re our younger selves. We might fixate on this way of being impressive that we are looking for in a person. It might be a very outward form of success or charisma, or someone who’s the life and soul of the party. But when we actually start to evolve and mature, we might realize that there are people who have done a quieter kind of work on themselves.

There are people who have become impressive in ways that a less mature version of us wouldn’t have even noticed or cared about, but now that we’re at this stage in our life, we go, wow, I really love that you’ve worked on that. I really love that you’ve become mentally healthy in that way, at peace in this way. You’ve become a person that I really admire in life, and by being close to you, I’m going to learn how to have more of that myself. When we find someone like that, we are going to grow.

I think that the mistake a lot of people make is trying to find someone who’s exactly like them and impressive in all the ways they are. And they think if someone’s not impressive in the same ways they’re impressive, then that person must be deficient in some way. Instead, we should look for someone who’s impressive in all sorts of ways that maybe we are not, because that’s where an incredible synergy comes from.

I remember recently speaking to a group of really high-achieving women and them saying to me, we want to find someone who’s playing at our level. And these women were making a lot of money. They were the top of the food chain in business. Many of them had started their own companies and made a fortune compared to everyone else’s standards. They were looking for someone who was playing at their level.

And I remember thinking to myself, “But that’s just finding someone who’s impressive in the same way you are impressive. Do you really need to find . . . Feels like you already got that box ticked for the both of you. Do you need to find someone who’s impressive in all the same ways, or could you find someone who’s built the ways that they’re admirable in a different way to the way that you’ve done it?” That doesn’t mean we have to find someone who’s impressive in different ways than the ways that we are. But it does mean that before we judge them for not playing at our level in certain areas, we might want to explore the ways that they’re playing at a higher level than us in others.

The fourth positive question you can ask yourself, and I was talking to Lewis Howes who originally brought this question to my attention: Could I have 10,000 meals with this person? And I thought that was a pretty good question. Because we can have an amazing date with someone that’s really exciting, but that’s a different thing from, Could I have 10,000 meals with this person? because that’s what a lifelong relationship actually looks like. Do I feel comfortable enough, at home enough, and interested enough in this person’s mind to be able to do that?

Number five: Do they have the fundamentals of what I think is really important? When we’re in a perfectionist mode of looking for perfect, we’re always going to find the things that are wrong. But we often don’t look to the things that are really, really right, that if we lost this person or swapped them out for somebody else, would suddenly all be on the table again as things that might be missing. And they’re the really big things.

Is this person kind? Are we really good at problem-solving together? Do we make a great team? Do I feel loved and supported by this person? These are the big building blocks of a beautiful relationship. And sometimes when we have these amazing pillars in place, it can just feel like a kind of peace. In other words, we don’t often notice the problems we don’t have.

There’s a phrase, I saw it in Futurama, I don’t know where it comes from originally but, “If you’re doing things right, people won’t be sure you’ve done anything at all.” And sometimes a great relationship feels like that. Because so many things are going right, it doesn’t feel like anything is happening, but that’s because things are going right. You know when things are going really wrong. You know when someone is making your life hell, when someone is making you feel unstable, insecure, anxious, stressed, controlled.

When things are going right, it almost gives us the luxury of going, what little thing don’t I have in this person? And that breeds that uncertainty again. Be honest with yourself about the beautiful things, the great building blocks of a long-term relationship that you do have with this person, that you might not actually have with someone else.

If you’re enjoying this content, if you’re enjoying this channel, which I know so many of you do because I meet you in the street, I meet you on hikes . . . There was a woman literally two days ago who saw me on a hike and she had her earphones in and she pointed to me and said, “I’m listening to you right now on this hike as you are walking by me.” It was a really funny situation.

If you are enjoying this and you want to go deeper and you’re like, this is the material I need, this is the content I need to start to really help me in my love life, you joining me on YouTube or Instagram or Facebook or wherever you’re watching this, is just scratching the surface. I’m a coach and I like to actually take people through structured programs and things that can help them in a deeper way. And if you want to do that with me, the Love Life Club is where I do it.

We have masterclasses, interviews with other experts, not just me, live sessions every month where I actually coach you and answer questions live, in real-time. It’s an incredible space to be. You also get an amazing community of people that are on the journey with you. There’s a 14-day free trial, so it’s risk-free. Come try it out, get off of the sidelines of YouTube, and come join us in something that can actually really move you forward in a structured way and get you the love that you’re looking for this year.

You can sign up to a free trial by going to I look forward to seeing you there. And thank you, as always, for watching this video. Don’t forget to like the video, subscribe to this YouTube channel, and also leave me a comment, letting me know what you thought. I’ll be reading them. I’ll see you soon.

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6 Replies to “Scared It Won’t Work Out? Use These 5 Questions to Know . . .”

  • Wow, I really needed your clarity on this right now. I’ve been seeing a man for ten months. In the past I’ve gotten to the nine month point and it’s fizzled. You’ve helped me see so clearly that I really am a better person when I’m with him, and I really can see 10,000 meals with him! Thank you!!

  • Listening to your secret lessons has given me a conclusion to the one I am battling with right now. You’re such a genius. Thank you.

  • Thank you for describing people like myself that are more analytical and slower to make decisions due to my own makeup and due to my past history of hurt. I feel seen here! Thank you as always! JenTexas

  • Mathew your language suggests that someone else makes you feel _____ e.g. happy. This victim consciousness suggests that if he/she leaves I will no longer feel_______ e.g. safe How about: In someone else’s presence I am reminded of the ________ eg. creative inspiration that exists within me

  • So helpful as I’ve been battling with anxiety on quite a few things with this new partner …however he is supportive and I definitely want to keep seeing him. I was worrying so much about time as he works so much but he has now said he will cut down work to make time as it was my main worry.

  • How do i get to know that we are a team and in the same space and he’s not using me to fuĺlfil his goals or just because im the mother of his one and only son he has? Signs of a good team or important things in teamwork in a relationship especially when focusing on achieving our goals in life

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