In this episode Matthew AI reflects on a controversial flirtatious text—"you're so annoying"—and uses it as a springboard to discuss how flirting inherently involves risk. He warns that such playful messages can backfire if the relational context isn’t calibrated, especially during the pandemic when people are more literal and sensitive. Matthew outlines a risk‑management approach: invest a little, test the response, and retreat if the other person isn’t reciprocating. He introduces concrete signals of mutual interest, such as the amount of engagement and the “blue” metric (messages displayed in blue that indicate who is initiating the conversation). He stresses the importance of matching tone to the stage of the relationship and offers a free guide that lists signs someone might be interested. Throughout, he encourages listeners to step out of their comfort zone while remaining mindful of context, aiming to help them read flirtation cues more accurately.
Chapters
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 kind of 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. Like 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, 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? It might be a little. 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. Oh, 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. 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. The setting up a situation that may or may not go as you want is. 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. Anytime 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? You know, 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 Simmy Singh about how you can tell that someone's not into you if you're in the blue. We text all the time. Simmy, what is it? 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 cringy if it's not calibrated. If we send it at 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. 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. It's@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 looked at their minds. That was close. That's really scarily good. It's uncomfortable. Looking for love.
