Is It Risky to Flirt with Him? How to Read His Signs

“WTF? Do not use this.”

This is a comment I received last week. It was in response to a flirty little text that I suggested you use with the guy who is on your mind right now. In fact, this text really seemed to divide people.

So, here is that response…

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So normally when I make a video, we do that concept, and then the next week, we move on to the next thing. Jameson wouldn’t let me do that this week because he said I had to comment on the comments from the last video.

To recap, the last video I gave a bunch of text messages that you could send someone to flirt from a distance. But there was one text message I gave as an example that was particularly divisive and, dare I say, unexpectedly controversial.


Send the person that you’re talking to a message that says, “You’re so annoying.” Now, that’s going to pique their interest. They’re going to ask, “Why?” When they say, “Why?,” you say, “Because you’re one of the main people who’s making staying at home so difficult right now.” Okay?


This might be the top comment: “Him: You’re so annoying. Me: What the actual fuck? Do not use this.”

So, she’s given that out as a public service announcement.

How on edge are you? If someone sends you a message saying, “You’re so annoying,” your first reaction is, “What the actual fuck?”

Well, I think it’s time we took things a little less seriously. That’s like the equivalent of a guy in a bar who you just brush past, and he looks at you and says, “You got a problem?” He’s already on edge. There’s something already going on there.

If the dynamic that you’re in with someone can’t support that level of playfulness, then it says more about the dynamic than it does about the message.

“Don’t do the first one, catastrophe potential.” Catastrophe potential! We’re in a pandemic. You would think that we’ve softened our language on what we term a catastrophe. What’s the potential for it to go wrong other than someone might go, “What do you mean?” And might be a little worried… “Oh what do you mean? Why am I so annoying?” “Because you’re one of the main people making staying at home so difficult right now.” “Oh, that’s nice. I thought you were being serious.” “No I wasn’t. It was just a joke because I like you.” Catastrophe?

And if you’re really worried that the person that you’re texting is too sensitive or too literal to understand that this is being said in a playful context – obviously don’t send this message on a day where you’ve just had a massive argument with someone – then you soften it. You say, “You’re so annoying,” dot, dot, dot. “You’re so annoying,” with an eye rolling emoji. “You’re so annoying,” emoji with the steam coming out the little man’s nostrils. You do that.

“How to potentially piss someone off with just a few sentences that set up a situation that may or may not go as you want.” This setting up a situation that may or may not go as you want, isn’t that flirting? That’s the part that I’m concerned about. I’m concerned we’re all a little serious. I’m concerned we’re all a little literal. And I’m concerned that what’s really happening here is fear of rejection masked as disapproval of the language of a message.

This message isn’t a perfect message. No message is. The whole point when I give you something to say is for it to get you thinking. Thinking about different ways of saying things, thinking about flirting in ways that you might not normally flirt, which could be a good thing. It can break someone’s pattern. It can get you outside your comfort zone too. We are inherently taking a risk any time we flirt with someone. We’re pushing just a little bit. We’re just pushing on that door, and we’re seeing what happens when we do. Does someone decide to open the door a little wider for us because they’re actually enjoying it, or do we get silence?

My brother always talks about this: Invest, then test. Right? Invest a little bit, show a little bit, be vulnerable a little bit, flirt a little bit, express you like someone a little bit, and then see if you get a little bit back. If you don’t, then don’t keep pushing on that door.

But the whole point of flirting is, at some point, someone needs to take a little bit of a risk. Now, we should be qualified in that risk, right? We should calculate a little bit, in the sense that have we had any signs that this person likes us at all? Do we know if this person is mutually attracted to us? We won’t know that until we start talking to someone.

And there are ways that we can know this just, literally, by measuring the amount of engagement they’re giving us. Jameson and I did a video with Simmi Singh about how you can tell that someone’s not into you if you’re “in the blue.”


Simmi Singh:

We text all the time.

Matthew Hussey:


Simmi Singh:

What is it?

Matthew Hussey:

Look at the colors. You’re in the blue, mate.


I coined the term “being in the blue” to describe the stream of messages on your screen that shows mostly those in blue that are from you.

Sending these messages to someone who hasn’t earned them or to somebody who clearly isn’t trying with you at all, that would be one step too far. And so, what I want the takeaway from this to be is, I need to start to calibrate where I actually am with someone. Something can easily feel cringey if it’s not calibrated. If we send it a time when the relationship hasn’t earned that message, or if it seems completely off key to the way we are the rest of the time, that’s when things can seem weird. But that’s not necessarily a reflection of how the message is bad, but more that I need to make sure the context is right to send that message.

If you want to know whether the context of what you have is right for these kinds of messages, I have a way that you can do that. We have a free guide that literally talks about the signs that someone might be interested in you. And if nothing else, then it will just raise your awareness a bit about the situation that you have with someone. So check that out. The link is here at It’s about as on the nose as it can be. Read through the guide. Super fast, super easy, but might help you feel either more cautious or more confident in sending some of the messages that I’ve been giving out.

All I had to do was throw out one little text, and then everybody loses their minds.

That was close.


That’s really scarily good. It was uncomfortable.

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40 Replies to “Is It Risky to Flirt with Him? How to Read His Signs”

  • Dearest Matt. What a video. I so admire and respect how you responded and the past post comments. I knew there’d be contraversy over that text as I have a dear friend who sends me text like that so. It doesn’t bother me as I know him well. Keep doing what your doing. I appreciate you (and Jameson)deeply and not just with you being my coach and mentor- but that absolutely spot on impression of the JOKER.!!!❤️

  • Hi Matthew
    I used that line…you’re annoying… And it was really amazing because moved the person to actually come and see me! well I had to reject the propose because in this period is not wise to meet other people, specially me that I work with sick one! Anyway continue doing what you do! Because of your Video’s I can say I have more courage to talk with men Thank you Alexandra from Holland

  • Dear Matthew
    I used “You so annoying “ on my guy and since then he stopped talking to me and took it literally.
    Im working in Saudi his was on holiday with his brother in Morocco now he has been stuck there since the airports have shutdown

  • Hahaha I literally tried the “you can’t come because you’ll distract me, and I can’t have that” in a text message. And he took it literally and replied “sorry..I’ve never been described as distracting. Hopefully it’s a compliment. Maybe another time.”
    Imagine if I’d called him annoying
    Dammit *insert face palm gif here

  • I’m not perfect, I’ll annoy you, piss you off, say stupid things, then take it back, but put that all aside, and you’ll never find a person who cares or loves you more than me.

  • Loved it!!
    When the relationship advice business dries up (probably never!!) you have another career Matthew! You comic timing is genius!!
    Love you guys thanks for all you are doing. You are helping my shattered heart

  • The annoyance will help you know what to do.

    If your friend is too sticky, you need to create a space between the two of you.

    If your friend is mean and hurt towards you, you should tell him how you feel.

    If you are unable to determine why you are so annoyed by your friend, you may need to do some self-evaluation.

  • You are a the best, Mat. And you know what? You and your team are very intelligent people, and of course want to help others with what you do. And, I sometimes feel we live in a world where the level of consciousness is on its “kindergarten” level. And so, when you talk about different things, some people do not receive the information with enough maturity and consciousness, first analyzing their situation and saying “ok, I’m not there, can’t do that”, and will “attack” and feel annoyed with a little flirty text you suggest. Fear, people act based on fear, and that’s where the “wtaf” comment comes from. And please I don’t want to be rude if someone else is reading this, but in order for people to follow you, they need a bit of common sense. When a person starts moving into consciousness, they begin taking things in a more gracious way. They start being more fun, funny, light…and of course stop taking everything so seriously, lol. And that’s who you are a fun, intelligent, warm hearted, conscious human being. That’s why I follow you.

    I know you already know this things, all your videos send a lovely meaningful message. And this video particularly with the “why so serious” Joker thing was brilliant. Just wanted to let you know that there are people who understand you in a deeper level and appreciate the wonderful work you do. Thank you.

    You make this world better place ❤️ Thank God for people like you.


  • Love the playful video and the true message about context! When I think of anyone I have ever experienced that would have been offended by this, there were other reasons at hand that were total red flags.

    I do wish there was a section of your site (maybe I am missing it somewhere?) where you guys would list all those site addresses for your different, awesome guides in one place. Well wishes to your whole team! Keep being amazing, guys!

  • I love that advice about “invest and then test… and, if you don’t get anything back don’t keep pushing on that door”. I’m working hard to resist the temptation to keep knocking on that door [lol]. Also, regarding the backlash of comments on the “you’re so annoying” flirt text… if that one is too “salty” and not someone’s usual flirt tone then yes there’s a chance it will go sideways, but I think you offered a great range of flirty text ideas to try out; flirting is just great light fun! (or it should be anyway)

  • I’m so in for those type of comments that let the curiosity linger in the air, those “what..wait…why..” and so the conversation continues. I’ve been using this kind of approach to chat on instagram with a guy, but there are lots of mixed signals.
    I react to his IG story with a comment to start the conversation, he replies with audio…sounds interesting, the flirting goes on, spatiated by a couple of hours… but the main topic is himself.
    Perhaps he is a narcissist? But keeps on joking about his flaws being vulnerable but confident about his own value while being humble and all at the same time! Irresistible, right? Lately I’ve been reading The agony of eros by Byung-Chul Han and got to the point that maybe narcissist are much fewer that we thought and there’s a “new type” of behaviour in the way people connect nowadays that results in an empty cycle and edulcorated culture.
    Going back to the root, I feel there’s something missing there, don’t know if it can grow over a little time and catch his attention or if it is a lost cause.
    Thank you all for this amazing content, always something to learn, meditate upon or having a wake up call.
    Ps If you have reached until here, double thank you, I might have vented a little I suppossed hahahaha

  • Yes yes and yes! I think people can adjust whatever advice you offer to their own situation. I kept trying many of your advice over the last year. Often thinking that they were not working but also questioning why they were not working for me. To realize the guys I was meeting were often simply not right for me and your advices helped me in moving on faster from them to not waste my time and energy. Also I was so afraid to be vulnerable and get rejected but I finally got less afraid to show more my nurturing side. Anyway I met a guy and when he invited me over for dinner I brought him some homemade muffins and Matt… that worked hahaha When he texted me the next day to thank me again and say they were delicious I smiled thinking of some of your advices to stay on his mind :) your advices work like magic with the right guy! Period! :) I found a gem and your advices so helped me to find him, appreciate him and hopefully continue the journey in his company! im also so grateful for all the ones with who it didnt work since I started dating again and for having seen it so quickly so i could be available for this amazing man.

  • You are so right Matthew… people are being way too serious in this time…I was thinking that you could send that you’re so annoying text in a little bit of a different way…
    … You are soooooooooooooo annoying lol
    when it is drawn out like that or even adding the lol at the end or beginning wherever you want it will definitely make it more playful …
    I personally think that everyone needs to start to laugh a bit more…I know that this is a very serious thing going on but laughter can heal and in the long run actually make you feel better…
    As always Matthew thank you for a great video

  • I didn’t send your text Matthew (actually didn’t read the suggestions, sorry!) HOWEVER, I did send this to a chap I’ve recently started chatting to:

    “this lockdown is now officially too long!! I was coping perfectly well until YOU came along looking all gorgeous” (added a kissy winky face)

    He responded immediately “How long have we got left? Another few weeks?

    Then “Single people should be allowed ‘isolation buddies’ !”

    1. Oh, I love this text you created so much, Susie! Well done and way to make it your own! :) Thanks for sharing this with us, Sara – MH Team

  • Amen! This video is spot on. If a guy is wound up so tight that a little “you’re so annoying” text sets him off, then he’s not for me. I think it’s a fantastic text to flirt and to get a little insight into who he is by his response.

  • Thanks! I’ve also used the “accidental cheeky word” on him in a text – instead of “to-do list” I may have said “to-do lust”… then I followed it up with ” *list ” and then “this is all your fault, getting me all lusty with your good looks”

    He LOVED it!

  • omg. i love that you talk about the way we use the word catastrophe! you’re spot on with this video & the last. life is full of risks. that’s what makes it exciting & fun! i’ve been texting with a guy since the beginning of the pandemic. we’ve both been self-quarantined for a month & a half. we’ve had 5 facetime dates that all lasted 3+ hours. we’re just now starting to flirt a little more. after our next facetime date, i’m going to use the annoying text. i think he’ll love it. thanks for the idea!

  • I see your advice kind of like a cheat sheet sort of thing like guidelines and if people aren’t switched on enough to adapt them or personalise them to suit their current status with a person then that’s on them for being sheep that follow with out questions and like to blame others for their failure. It doesn’t take alot to figure out a funny face would lighten that whole your annoying approach but to be honest I’d be more worried about the type of person I’m involved with if they kick off at me for that rather than caring about the potential problem and wanting to find a fix and what I mean by that is I should feel safe enough with my partner or whoever to express if I’m actually annoyed without the fear of being yelled at without discussing it first that’s deflection and that worrying behaviour yes when you talk about the reason why you are annoyed with them it may get heated and that’s well within their rights if they find it offensive but alot of people are forgetting that’s not the same as being easily set off and instead of admittance to being in something thats isn’t healthy they project blame outward and heighten the importance by calling it a word like catastrophie so it shifts attention x

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