The BIGGEST Male Insecurities in Dating Revealed…

The video this week is all about bravery and kindness, and my goal is that by the end of it, you will understand and be able to relate to men a little better.

We asked MEN about their specific insecurities when it comes to early dating . . . 

Which revelation surprised you the most? I look forward to reading your thoughts as we continue this discussion . . .

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This morning, I put up a post on Facebook and Instagram asking men specifically, what’s an insecurity you have in early dating? And the responses were so beautiful, and so vulnerable, and so real that I felt compelled to make a video about it.

“Is she even into me?” “Wondering how I compare to the competition and her previous boyfriends.” “Will she be able to understand the emotions or the side of me that people don’t usually see or I don’t normally let out?” “That I’m not good enough” says Dave, “But interesting enough to be on the short list. “Financial expectations.” Another person says, “Can I provide enough?” Someone else says “Not being man enough.” “Their past relationships.” “Getting friend zoned.” “Am I too boring? Will I get found out?” “Am I enough? And can I please her?” “Is she really interested in me?” “Third date ideas.” Someone says. That one really made me laugh out loud when I read it because it’s really true. First date, drink. Second date, movie. Third date. As a guy, you get to a point where you think, is there anything else in the world to do? “That when we get past all the initial flirting and banter, she won’t like what’s left.”

Another theme is that if I show my interest, they will lose theirs. There was a comment here from Ryan who said, “Texting anxiety is the biggest one for me. Purposefully spreading out response times to not come across as too available, in order to keep her interest. It becomes a game, a game I don’t want to play, but am forced to play. If I respond too quick, the pattern has been that she loses interest because the chase is over and she’ll spend more time chasing another guy who seems less interested.” Not to be too dramatic, but this is a bit like nuclear war Jameson.




Every country has to make the other country think that it will nuke them if they have to, even if secretly, they don’t have any intention to, because of, what’s it called Jameson?


Mutually assured destruction.


Mutually assured destruction. Except in dating, in our love lives, all of this posturing, all of this game theory creates mutually assured isolation. I was really touched not only by the male responses to this post, but by the ways that women spoke about their reaction to the men’s comments. Morgan said, “I’m going to start reading this thread before every date. These comments make me believe that real vulnerable men still exist. I’m here to gain knowledge from their side.”

I never know how a question like this is going to go down on social media. Are people really going to be vulnerable? Are they really going to be honest? Is this going to be antagonistic in the comments or is it going to bring people together? What was so beautiful about this is how profoundly it brought people together, that it created this collective pressure valve and catharsis where everyone got to go “Huh, we’re all the same.” It’s a bit like everyone gets to see through the Matrix for a brief moment and see how the world actually is beneath all of the facades, beneath all of the things I’ve been led to believe about the other gender. I now get to see who people really are. They are me.

The part that really sucks about insecurity is that, we can feel insecure about something in the case of the men replying to this post, insecure about not being attractive enough, not being manly enough, not being successful enough. We can feel insecure about those things. But then on top of that, we end up feeling insecure about being insecure. Not only am I insecure that I’m not going to live up to her past boyfriends, I’m also insecure that she’s going to find my insecurity about that disgusting. That the very act of being insecure about that is going to turn her off. So now I feel insecure about the competition from the past that I feel like I’m competing with, but I don’t dare say it because if she knows that I’m insecure about that, she’s going to find that insecurity a turnoff. And we’re not crazy for thinking that about each other.

Look, if this post proves anything, it’s that there are plenty of amazing people that love vulnerability and want to see more of it. But we’re not wrong for feeling like, if I reveal my insecurity, that could make me unattractive because there are some people that see insecurity and go yuck. It may even have been us at points that felt that way, even though we would never describe it in such mean terms, we might have felt turned off by insecurity in the past, or even subconsciously, we might find ourselves repelled by insecurity.

Now we would think that insecurity would bring us closer together, because if I see your insecurity, then I’m able to see that, oh, we are not so different. And therefore, that can help create a connection. Well that’s the positive side of vulnerability. But what if seeing insecurity in someone else reminds us of something we don’t like about ourselves? Something we’ve tried to banish from ourselves, something we are trying to run away from in ourselves, something we are trying to suffocate in ourselves by dating someone, that we think is so attractive and sure of themselves and desirable that by being with them, we will finally be enough and won’t have these insecurities anymore. If I date you with all of your insecurities, that’s not going to get me out of my insecurities, it’s just going to remind me of them. I don’t want to be like this, in fact, I hate this part of myself. I have contempt for this part of myself. I don’t want to be around you. You’re going to infect me with more of that.

If you think about it, so many of these guys in this post are describing this feeling of needing to play a game. How often should I text? How much should I text? How much should I reveal? How much should I show interest in this person? There’s this constant feeling of, I need to play some kind of a game or she’s going to lose interest. She’s going to decide that she’s worked me out and she’s going to go and find someone more mysterious. I’m going to lose any shred of power, or dignity, or control over this situation and I’m going to pay the price for that in rejection.

Well, when someone sticks their neck out to say something or to try with us, rather than be coy, rather than use it as an opportunity to claim power and be in control, we can encourage that effort. Someone could send us a text in the morning and rather than just reply, we could say later that day, “I really liked it when you texted me this morning, it felt good to hear from you.” And in that moment, someone gets confirmation, “Ah, I don’t need to play a game here. I’m not guessing whether she liked it. She told me that she liked it. And that gives me a feeling of strength in wanting to put down my weapons and keep stepping forward.” So many of us aren’t rewarding other people’s bravery. We’re rewarding the opposite. Ask yourself a question right now.

Do I repeatedly in my life reward kindness and bravery on the part of the people I’m trying to attract, or do I reward the opposite of those things? Meanness, indifference, a nonchalant, nonplussed attitude towards me? Do I respond to someone making me second guess myself? Do I respond to somebody who makes me question whether they like me? If you are someone who continuously rewards the opposite of kindness and bravery, I will tell you why you keep getting hurt in your love life. The other recipe for getting hurt in your love life, while we’re on the subject, is if you stick your neck out in a brave way, but when someone doesn’t reward that with their kindness and their bravery, you keep sticking your neck out. A recipe for success in love is follow kindness and bravery. Be kindness and bravery. And then when you get it back, follow that path. When you don’t get it back, use it as an instant signal to redirect your energy in a direction where kindness and bravery lie.

And lastly, I hope this post can make us all a little less susceptible to the kind of voices, especially online, that seek to divide us by constantly making snarky or contemptuous comments about the other gender, in whatever direction that goes in. Thank you for watching. If you liked this video, hit the like button. If you want to join this community of like-minded people, who want to understand each other better, and create a really beautiful place for growth, and healing, and confidence, then hit subscribe on this channel. And also don’t forget to hit the notification bell if you want to be notified the next time I bring out a video. Also feel free to leave me a comment underneath letting me know how this video affected you, and what it means to you. I look forward to reading them.

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11 Replies to “The BIGGEST Male Insecurities in Dating Revealed…”

  • I bought the 59 scripts and did not get them. I’m not sure how to get in touch with someone regarding this. I emailed and have not gotten a response.

    Tammy Ruddle 931-982-9346

  • Thank you Matthew for addressing us as a person here. Great new video on insecurities. Need a where they came to be Freudian/ Matthew slips.

  • Dear mathew, ok responsed about in the first dates. Yes, of course.
    But my problem is..that I lived 10 years in in thoughts, that I dont need man, because my ex really brokemy heart. But nowadays I completly now, processing with my self, that I need man. One proper, honest and gentle man, which make and have his own money. I dream about man, like you. Can I dream a little bit?
    Hope, you answer me.

  • love offer kindness and bravery and floow kindness and bravey – winning rules to guide me!
    thanks Matthew

  • Hi Matthew I looking for advice. I am seeing a guy who has felt comfortable enough to tell me he suffers with some mental health issues. We were due to meet after his friends bbq and he got drunk and stood me up after spending the day telling me he couldnt wait to see me. I have messaged saying its ok and that Im not angry I just want to know he is ok and that we are ok but have heard nothing from him. What do I do?

  • Wow thank you for the reward and adress bravery- part! Yes I always only replied to the good morning texts but never said how much I like getting these good morning texts- definitely will do the next time!

  • Matthew, thank you for this thought provoking video. It’s made me remember times I could have been more supportive and less dismissive of ex-partners insecurities. I’m lucky to be in a great relationship with an amazing man who’s kind and brave. It’s a good lesson to look for ways to reward and show appreciation for all the little things he says and does that show he loves me. I’ve followed your programs and masterclasses for years and your advice really works! I appreciate all you do, I know you really care about helping people find and keep love.

  • I am so grateful to hear there are men in today’s world who WANT a committed relationship leading to marriage. I am presently dating someone and I really loved what you said about how to respond when he texts me.

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