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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.

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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?

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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.”

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Simmi Singh:

We text all the time.

Matthew Hussey:

Simmi.

Simmi Singh:

What is it?

Matthew Hussey:

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

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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 DoesHeLikeYou.com. 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.

Jameson:

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”

  • “Fear of rejection masked as disapproval of the language of the message” I think your concern might be right on point.

    But that somewhat unpredictable result is what makes flirting so exciting… I love how my heart starts racing everytime I send a particularly flirty text, and waiting for the response is equaly exhilarating.

    You can and should take into consideration the context but don’t overthink it… In the end the truth is that each person is different, so you can’t really be 100% certain of how someone is going to react. Their response might not be what you hoped it would be, but it might just be what you needed. Worst case scenario he goes away. Do you really want to be with someone who takes themselves so seriously that they can’t handle a simple “you’re so annoying” text? I don’t…

    In my particular case, I take your texts as more of an idea than a copy and paste, especially since I have to translate them, but they do work!

    Anyway, haters gonna hate. I think, most your followers already know what you and your team are all about. That’s why we follow and love all of you <3

  • You’re spot on! This isn’t a text to be broken out on the first day. But once you’ve gone back and forth a bit qnd have gotten a sense of each other’s humor, it’s genius! And if you’re at all worried about sending it as a plain sentence, that’s what they make the winking emoji for. You’re so annoying ;-)

  • I sent this to a girl that I have a great relationship with and we flirt quite a bit. But we live in different countries When I first heard it I thought it was brilliant cos the first part is misleading, and they get a bit taken a back. But then you follow up with the compliment. Result? She loved it! She replied with, ‘you know how to make me smile ’

  • I agree with you, Matthew: that text reveals the dynamic of the relationship. In other words, can you be playful with each other? I sent it to my boyfriend, and he loved it. It resulted in a few more flirtatious text after that. If you can’t be playful with your partner, that may be a bad sign.

  • I thought it was cute! I’ve received a text that I had to read a couple of times before I responded … “wth are you doing” after the second read I responded … “wth do you need to know” … he called me immediately and was laughing when I picked up! Why so serious!?!?!?!?!

  • Dear Matthew! The signs you described are pretty much too much. You said you would give us a tip about giving some guy a flirt or not. Some signs of his interest *before* getting into the thing would save us from a fear of rejection.
    The signs you gave work for a connection that is already there for God’s sake))
    Could you talk more about the signs of interest from a guy one hasn’t yet had a lot of phonecalls, been to a movie, slept with etc. The thing for the very beginning.

  • I say wtaf, to all those who have flipped out about this piece of actually very good advice which does work if the connection and context is already developing. I mean do you really want to be with a guy who takes it the wrong way in this already very serious world we’re living in?! Everyone needs to take a chill pill! Sorry you had to deal with Matt! I’m sure the majority of us knew what you were saying!

    1. Hi Rosemary – thanks so much for reaching out to us and we’re sorry you’re having trouble finding the link. I wanted to let you know that we received your request and one of our team members will be reaching out to you via email to help you with this. Talk to you soon, Sara – MH Team

  • Prior to you mentioning the, you’re so annoying, I said this to a guy the same thing, then a cute comment, he loved it!

  • Matt. I can get a guy, but I’m currently looking for my husband and that has become more and more challenging. I have been online dating. Especially because now I’m outside of the states, but too many persons, just seem as though they are not ready even though they say they are or they just seem to want to get in bed. And that is not going to happen. I’m not going to give someone 5 years of my life to purpose. I know where I’m at in my life and I want someone who is also there and proactively is seeking that. I’m not willing to slow my progress because someone else is not there as yet not going to happen. I see marriage as just a portion of my life. I have other things to accomplish as well. So I don’t want to give it more time than I need to. Please help.

  • I watched that video and must be honest with you – I wouldn’t send that message even to a man that I am sleeping with. It gets to their head and they usually don’t even know how to take. it – such texts make men claustrophobic and smug :)

  • You are so right, Matt! I am surprised that some women got that soo wrong. Definitely not a phrase for people without humor or playfulness…

  • Bit creepy… and not just your joker impression :p honestly thought when I opened this video…. ‘where is he going with this…. surely flirting is a little risky?” I thought that text was genius!

  • Now he sees the funny side. Now he’s always smiling!
    LOL
    Totally loved this.
    And I agree completely-context and a foundation does wonders.
    Then rock it the heck out.

    I personally said something similar to this to a guy I dated a while ago (albeit it was in person, and I had known the guy for a bit). I also meant everything I said-which I think matters. I was genuinely annoyed. It went pretty well! ;)

    Me: “GOD, you’re annoying!”
    Him: *laughs* “What? Why?”
    Me: “You’re handsome. You’re ridiculously charming. You’re good at EVERYTHING… like, can you not? It’s annoying.”
    Him: *SMILES* “Ahhhh, I see. That sounds terrible. I’ll have to work on that. *pause* “I’m definitely going to kiss you now.”

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