Flirting 101

Feb 3, 2026

TRANSCRIPT

Today we are going back to the roots, back to the essentials, the starting point for every relationship, situationship, hookup, one night stand, three night stand, eleven night stand, and at that point it's just relationship again, so we're back to the top.

It has been a minute since I have gone back to the basics to do a flirting 101 type episode. And the best part about these types of episodes is that there will always be someone at this place. There will always be someone that this type of episode will benefit. Flirting and the art of flirting will never go out of style.

This episode and this conversation will always be useful and important and valuable information for somebody at one point or another. Whether you're just starting out with dating or whether you've been dating for a long time, whether you just got out of a relationship, whether you're looking to go into a relationship, like flirting is always going to be relevant in every guy's life. Like it is always going to be something that

we need to do. Like it is just something that we have to do if we want to get in a relationship, if you want to hook up with somebody, if you want to meet somebody, like you just, you have to flirt and you have to know how to flirt. And I think everybody can improve improve improve. I think everybody can improve their flirting game. I think flirting is an art. I think it's hard. I think it's intimidating. I think it's stressful. I think it's anxiety inducing. Like I think it's all of the things

that you can think of and in this episode I am going to give you advice on how to get out of your head and into the zone and into a good mindset, a confident mindset around flirting. There will always be a guy going to flirt with a girl from Adam and Eve to you at the bar this weekend. Like there is always going to be more things to learn.

Josh Felgoise (02:22.998)

or a different way to see things or a different mindset to develop when it comes to flirting. And I want to begin this episode with a big disclaimer that I am no dating expert. I am absolutely the farthest thing from a dating expert. I have had my fair share of flops. I have had rejections. I have had mishaps. I have had missteps. I have made mistakes. I have fallen flat on my face. I have also fallen in love. I have fallen out of love. I have fallen back in love.

I don't think I understood what love was and I think I do now and along the way I have learned how to flirt or at least I have tried to flirt and I think those are my credentials for this episode and I don't think you need to be a dating expert to give advice on this type of thing I don't think there is such a thing as a dating expert like what quantifies or qualifies I think it's qualifies what qualifies somebody's dating expert like that they've gotten into relationship okay then like

dating expert, like, no, I think that if you have put yourself out there, if you have tried to flirt, if you have done it, then you're qualified to share your advice and your opinion on it. And this is not a dating show, but I often talk about dating because these are some of the most popular episodes of Guy Set. Why is that, you may ask?

Because everybody wants to date, like everybody wants to love and everybody wants to be loved. It is the universal experience that everybody is either trying to find love, hold love, keep love, stay in love, fall in love, all of those things. It is one of the goals that I think every human collectively shares. I think it is one of the things that we can all agree is universal, that everybody wants love.

So I take it upon myself on a show I called Guy Set, and every week I say is a guy's guide to what should be talked about, to give my advice on how to make this all a little easier. And I found out a statistic recently that 50 % of guys 18 to 25 years old have never asked a girl out in person. And I think I can help out with that. I think I am uniquely...

Josh Felgoise (04:41.497)

I think I'm in unique position to help out with that because I started a podcast to talk about this type of stuff and because I think that guys don't talk about this stuff enough for so many different reasons, a myriad of reasons if you will, because dating and talking about how you are feeling awkward around flirting or you feel embarrassed around flirting or that you have a fear of rejection around flirting is embarrassing. That is also another universal truth that

feeling embarrassed is a reason we don't talk about it. And I hope that I can help out with this today. And if you're here looking for advice, I really hope that you leave with some and I think you will. So stick with me. I hope that you leave this episode with a little more confidence to try to flirt, to be okay with the potential of rejection and an intention to walk up to somebody at a bar or at a place or at a pregame or at a party.

wherever you are, whatever setting you're in, with an intention to flirt more, so that the next time you find yourself in that position where you see someone and you think, I should go up and say hi, like, I think that person's really cute, like, I wanna go say hi, you hear me saying, here is how to do that, with a little more confidence. And I think, honestly, a lot of girls prefer that guys make the first move.

Maybe even further than like prefer it, I think a lot of girls rely on it and expect it. And that means the best thing you can do is get more comfortable flirting and get more comfortable talking to girls. Now, I know all of the fears and anxieties associated with this. I promise you, I know them very well. There is an intimidation factor, there's a nervousness, and I think probably the biggest one

is the fear of rejection, the fear of falling flat on your face and the potential of looking like an absolute idiot and leaving feeling completely and utterly embarrassed, of feeling like you're not cute enough or you're not charming enough or you're not good enough, of in general leaving that reaction with lowered self-esteem. And I think a lot of us have a story or two or seven that have

Josh Felgoise (07:02.804)

created this fear for us or perpetuated this fear for us. We feared we would get rejected and we did and we proved the biggest fear which now holds you back from trying again. Whether it was in middle school or in high school or in college or last week, I think we all as guys have at least one story that we hold in our heads.

of rejection, of putting ourselves out there and feeling like we were rejected, of getting rejected. So I'm gonna start this with one of my stories, one of my many stories, one of the earliest flirting stories that I can remember when I first moved to New York a few years ago, a long, long time ago in a land far, far away, like 10 blocks down from where I am right now, and like not that many years ago.

A time of many times where I felt that way, where I left feeling like shit. Where I left feeling like, shit, here we go again. Of feeling like I read the situation wrong and felt like I laid it on too strong. And I'm not telling you this with the intention of embarrassing myself or airing out my own dirty laundry, but I am telling you this to let you know that somebody else has been here.

and that everybody else has been here. It is just not talked about because it's embarrassing to share this sort of thing. It just is. To set the scene, it is a Friday night in the East Village of New York City. I remember this so vividly. It was a bar called Downtown Social, which is a massive bar and it gets like super rowdy around like 2 to 4 a.m.

I'm with a few friends and one of my friends starts talking to this girl and it seems to be going well so I'm like maybe I should go walk up to her friend who's also with a few other friends and I kind of just led with like hey and she was like hi and I knew right from there like her high was like hi like hi like get out get the fuck away from me and I knew right from there that like she just wasn't that interested and like

Josh Felgoise (09:12.465)

was kind of like, like not again, like not another fucking guy, like ugh. So then she was like, hi, and I was like, how's it going? And she was like, fine. And I was like, ugh, okay, like this is already not going well, but I got out of my head, I decided to put myself out there, I decided to try and give myself like a, you know, like the feeling of when you build up confidence, you're like, I'm gonna go do this, I'm gonna do this. And then you do it you're just like, fuck. So I'm like, all right, I did it, I'm gonna keep it going for like a little longer because I got myself here.

So then I was just like, she was like, fine. And I was just like, okay, cool, cool, cool. So like, do you come here often? Which is like the classic line that I thought you're like supposed to say. And she was like, no. And I was like, cool, cool, cool, cool. Okay, okay, okay. And now I'm like talking to the whole friend group as if I'm like a comedian, like reading the room. I'm like, how does everybody know each other? Like, blah, blah, blah. Like I'm like trying to entertain. And I was just kind of like a dog with a bone at this point. Like I was interested in like, I was just not catching the hint, even though I knew I was, I knew the hint, you know?

And she was like, these are my friends. And I was like, got it, got it. Like school friends, like high school friends, college friends. And she was like, yeah.

And I was like, nice, which one? Like high school, college, school, which one? And she was just like, yeah, like they're my friends. And I was like, yeah, yeah, got it, got it. So like, did you meet them from somewhere? Like, are they new friends from tonight? Old friends, family friends, like street friends? What are they? Like, where'd you find them? And she was just like, college.

And at that point, like I was just like, okay, like, like she couldn't have been less interested if she tried. Like she was giving me like one word answers, like just not interested, not engaged, like body language was not there. And I was just trying, like I was literally, I was just trying and it sucked because I was just like, okay. Like that sounds awesome. Like happy to hear that. Like you made friends in college and you know, like

Josh Felgoise (11:17.46)

At that point I was like, all right, like she's not interested. So then I was just like, it was nice to meet you. And like, she kind of just like turned away. And I feel like that interaction really took a hit on my confidence. Like for the rest of my night, I was like, Oh, well that sucked. And like, she didn't have to be like that. Like she didn't owe me anything and didn't have to respond to me and could have, you know, like she didn't owe me anything in this interaction. And I also could have taken the hint, but it was just like one of those really

really tough interactions and I'm not telling you this to embarrass myself, I'm telling you this because I have done that before, that's happened to me multiple times before and I think that every guy has had a moment like this, whether it's at a party or a pregame or a hangout in high school or in college or last week, like, and I definitely let it get me down and looking back,

What I wish I had done was turned around and been like, all right, like kind of onto the next, like this didn't work, but like I'm gonna, I'm gonna shoot my shot again. Like I'm gonna try and find somebody else to talk to and like keep my confidence up. But instead I turned around and I was like, all right, another drink. Like let me like get super drunk because I am upset. And those experiences can be kind of scarring. Like those experiences of being turned down or like turned around or they turn your back on you like.

That fucking sucks! Like those experiences suck and there's no other way around that. And it's the same feeling of being rejected or being ghosted or any of that stuff. those experiences can be really scarring and they can take a real big hit on your confidence and your mindset and your ability to put yourself out there or try again. And I sincerely wish I didn't let that get to me for as long as I did. And here's how I would have done that differently.

I should have just taken the hint earlier from one of the times where she was just like yeah and Been like alright like have a good one and just kind of moved right along and I'm not gonna talk you through all the different things I wish I had said the things I had done differently because I'm not a big believer in picking apart interactions either because I could sit here all day and say like I wish I had asked this question earlier or

Josh Felgoise (13:32.816)

not let it linger for so long or not just said, hey, or not said, do you come here often with or who are these people or like all the weird things that I did say in those moments. Like I could pick that apart. Like I'm doing right this second for so long. I really could do that for a while. And I'm just not a big believer in that anymore because I don't think it gets you anywhere. Like I used to be that type of person where I would sit, I would leave that night and be like, fuck, I should have done this differently. I should have done that differently. I wish I said this. I wish I said that. Like I should have asked a question more. I should have smiled more. I should have nodded more. I should have like, no, like.

The more you pick apart the interactions, the more you just drive yourself insane. The more you stay in that moment and overanalyze and over like index this moment for yourself, like the worse it gets because you just feel worse and worse about yourself. So I'm now a big believer in just moving on to the next, accepting that that is what you did in the moment. It didn't work out.

And now you kind of have that information about that interaction and you can now go try something different or change your way in or your confidence toward that moment. Had I been less awkward, maybe it would have gone differently. Sure. Had I done this thing, maybe it would have gone differently. Had I done this or that or whatever, like there are so many different things you can spin yourself into a cycle about. And my advice here is to stop putting your interactions under a microscope.

especially when you're putting yourself out there and trying to be confident and trying to like believe in yourself for a little bit. Stop thinking so deeply and intensely about every interaction you've had. As I recall, an extreme and excruciating detail interaction that I had from three years ago. I never said I wasn't a hypocrite, but like I seriously do mean that like.

The only reason I have that so deeply ingrained inside my brain is because I spent so much time thinking and overthinking about that specific interaction. I spent so much time analyzing the way I was weird or uncool or kind of like beating myself up for what was otherwise a pretty harmless and awkward interaction, which everybody has. Like there's really no harm in that. That's why I say it was harmless. So stop beating yourself up for being awkward. We're all awkward.

Josh Felgoise (15:46.706)

We all say the wrong thing or wish we could have said something differently instead of beating yourself up for it. Use it as information or like Intel about, okay, I did that last time. I want to change that up. I don't want to do that again. I want to do something a little bit differently. Like, okay, now that I did that, I'm going to try something different. I'm going to use a different tactic or a different pickup line or say something a little bit differently or smile or like

Like, now that I did that, I'm going to try something else. Maybe I will stand up a little taller, or be a little bit more confident in myself, or ask a question that I'm actually curious about, or give a compliment that I actually mean, instead of saying the thing that I think I'm supposed to say. And I think that is the first and most important role when going into flirting. Let it all go. To the best of your ability, try not to overthink and analyze everything you say and every move you make.

Go into each interaction with a clear headspace, forgetting about the past interactions you've had, because those are over. This person is not the last person. This girl that you're talking to is not the last girl that you fumbled. This is a completely new opportunity, so do not bring your baggage from the last one to this one. This is an entirely new flight with new passengers and new flight attendants, and you are the pilot.

You can choose to take off in an entirely new direction and get to 10,000 feet again, like you don't have to just not take off again. You can try and land the plane well. may be a little rocky. There may be some turbulence, but you don't have to crash just because you crashed last time. This flight has the potential to be your smoothest yet. So don't act like it's the last flight.

So here is how I would go into a new interaction of flirting. A couple things that I think you are completely in control of are making good eye contact, not looking up at the ceiling or behind her or at her feet or at her boobs, like look nowhere else beside her eyes and make good eye contact. Like not like, like you're not like staring into her soul, but like you're making eye contact. That means that you're there, that you're present, that you're genuinely interested.

Josh Felgoise (18:07.036)

Your body language also matters here, like you're not crossing your arms, you're nodding, you're staying engaged in the conversation. I also think your posture is really important here, like you're not slouching, you're not crossing your legs or your arms or whatever, like you're standing up tall, not to like a super tall, like super insane point where you're like eyes are open and you're nodding and you're smiling. Like you don't want to do that. Like you don't want to look crazy, but I think

All of these things do make you look more confident when you're standing up tall, when you're present, when your arms aren't crossed, when your hands aren't in your pockets, when you're not holding your phone, when you're making eye contact, when you're nodding, when you're smiling, when you're present. All of the things that you think a present person would do, do that. And I think your body language says a lot about you before you even say anything.

You're smiling, you're nodding, you're standing up tall, and you have like a normal energy, a normal, calm, and relaxed energy where you're paying attention to these things. Like you're not super insane or intense about them, but you're paying attention and trying to look as confident as you want to. Something else you can do to like seem present is to laugh when she's saying something. If like you can tell that it's a joke or she's like saying something kind of silly, you can be like, not like,

Don't be crazy, but like just be normal, be relaxed, be calm, and be excited to be there. This is an entirely new opportunity that you have in front of you. These are all of the things you can do before you even say anything. When you go to walk up to somebody, think about these things and be super relaxed. Another thing I would say is don't go up to a big group of girls when you're on a solo mission. None of us are ready to take on an entire galaxy as a solo astronaut like

Do not walk up to everybody at once and just be like, hey, like you, and she's like with a group of eight friends and she's just like, what? Like, no, I would say walk up to like one or two girls at most and just be like, hey, how's it going? Or like, hey, I think you're really cute or whatever you want to say. Like you don't have to have some premeditated pickup line. Like is this seat taken? Like you can, if you want, like they might think that's funny. Like if that's you, by all means do that.

Josh Felgoise (20:25.65)

Just say whatever you are most comfortable with. I'm not going to give you a line that you have to say because I do think every interaction is different and every person is different. whatever you are most comfortable with saying is what you should say. Like, hey, hi, it's nice to meet you. Or not, hey, hi, not, not, hey, hi, but like, hi, I'm Josh. Nice to meet you. I think that works. Like I do. I think just introducing yourself to somebody is a, is a very fine thing to do or just like, Hey, I'm Josh. I think you're really cute. It's nice to meet you. A compliment.

Compliment goes as goes such a long way. Like everybody loves a compliment. I love a compliment. You love a compliment. Give them a compliment. That's a great way in I think saying hi, how are you? Like, um, who are you here with? Like have you, I don't think like the, do you come here in line? Do you come here often line? Like isn't bad. Like have you been here before? Like what's your favorite? Like what do you like to drink? Like if she's drinking, like give her a compliment on what she's wearing or her hair or her eyes. Like

People love a compliment. If you don't know what to say, like, I think it always works to compliment somebody on their eyes. Be like, I think your eyes are so pretty. And she'd be like, thank you so much. Or I think your hair is really pretty. Or like, whatever. Like, just compliment them on something that you actually genuinely want to compliment them on. And then from there, ask questions and be genuinely interested in her answers.

This isn't about like getting answers. This isn't about like getting to really know her. It's about following up on what she's saying and like actually kind of starting some sort of a conversation here. Like whatever you can do to continue the conversation by asking follow up questions. That is what you should be doing. You don't have to know her last name or her who where she lives or what she does in this interaction. You just want to keep a conversation going and like be interested.

Also, depending on your level of comfortability here, like you can be touchy because I think that is a very big signal that you are in fact flirting if there was any confusion around this, but not too touchy. Like, please, by all means, do not be too touchy. Like, do not be creepy. Like, you know, obviously, like a little arm touch is like the best thing to do here. And I think that is a signal or a sign from both sides that the person is interested. But like only if you're comfortable doing this, if that's something that you do or you want to do.

Josh Felgoise (22:48.244)

And that's like a little bit into the conversation. Like you're like laughing, you're like ha ha ha, like arm touch. You know what mean? Like just like when it's normal, when it naturally flows, you're not gonna like run up to him and be like, hi, I'm Josh, nice to meet you. And like smile, nod, like ha ha ha. Like don't do all the things like too much. Everything has to be at a level that's like normal. If you think it's not normal, it is not normal. Do it at a calm, collected, like excited, but like cool guy level. Like just, you have to a little bit fake it till you make it here.

And I think nobody really has all of this down when it comes to flirting. I don't think anybody is like a master expert flirter. Some people are much better at better at it than others. Like I have some friends who were just like naturally gifted at going up to somebody and saying hi, like naturally gifted when we're at a bar to like walk up to a girl and be like, hey, how do they just do that? Like what? And I'm sure you have that friend too. And you're like, how the fuck are they so good at that? And why am I such a fucking loser? Like it just comes more naturally to some. But I still think everybody is a little awkward in it. But like some people just have

more confidence. Also, some people just have more experience with it. Some people have just done it more and have built up the reps to have the confidence in themselves. The people that have built up the reps, by the way, have also been rejected a ton of times. They just don't let it get to them as much as I did or as much as somebody who like let to get to them does. You know what I mean? Like the person who is really confident in going up to somebody, I guarantee you they've been rejected more times than all of us. They just don't let it bog them down.

They just kind of have that mindset that I wish I had earlier where I was just like, okay, like she wasn't interested. She doesn't have to be not everybody's going to like you and not, I don't like everybody. So it doesn't make any sense for everyone to like me. So onto the next. And that is the mindset that they have. It's a confidence. It's like an air to them that they have. And that's what I say, like fake it till you make it a little bit. Like you have to put the reps in, order to gain that confidence and that mindset around flirting. So you have to put yourself out there to get that confidence, to develop that mindset.

And then finally, you do not know this person, but I'm sure you want to. So that is why it is all about the clothes. You want to ask for their number, not their Instagram, not their Snapchat. We're too old for that now. Their phone number, because you want to text them. You want this interaction, this flirting to result in texting them and then being able to text them later to be like, hey, it's Josh from the bar.

Josh Felgoise (25:11.792)

I'd love to see you again or hey, it's Josh from the bar. Like I loved meeting you or I loved talking to you about this thing. Hey, it's Josh from the bar. I'd love to grab drinks. Are you free sometime Thursday or hey, it's Josh from the bar and the meaning like you put in the bar. I think this is a good thing to do by the way. Like after you meet somebody, I gave this advice recently as well in one of the dear guy set episodes. After you meet somebody and when you go to text them first, say your name and then say where you met them.

just to like have it clear for them. Like, okay, that was that person that I met. So I would say, hey, it's Josh from X-Bar, wherever you were. And then I would either give them some sort of compliment. Like, I really loved meeting you or I loved talking to you about this thing. If there was something that was super memorable from the conversation. And if not, you can just say like, hey, it's Josh from this bar. Like, I'd love to grab a drink sometime next week. When are you free?

Or if you want to be like a little bit more assertive, which I think a lot of girls like, you could just say, Hey, it's Josh from this bar. are you free this Thursday at 7pm to grab drinks or are you free Wednesday at 7 30 to grab drinks and then see from there. And if you don't want to be that forward, you can just say, Hey, it's Josh from the bar. Like loved meeting you tonight. And like, I'd love to see you again. And I'm sure she'll give it a little heart, a double tap heart and say like love meeting you too.

And then from there you can ask about the drinks. Like it might be a better second text sometimes too. Totally up to you, totally situational, and depending upon your level of comfort in texting and assertiveness and all of that. And if you're nervous, I honestly think having a friend with you is always a great idea. Like wingmaning is a good thing. Having a friend that will walk up with you and start a conversation alongside you or talk to the friend while you talk to the other friend.

is always great. Like that is always a good tactic here, especially if you're nervous, especially if you're just starting this and you don't know how to go in first. Like going up with a friend is a great idea. Flirting is so much more simple than we all make it. Like it seems like this huge mountain that we have to scale and we make it out to be this huge thing in our heads. But at the end of the day, it's just walking up to somebody and introducing yourself. It's just walking up to somebody saying hi, asking for their number.

Josh Felgoise (27:30.542)

and being excited about seeing them sometime soon. And then leaving feeling excited and giddy and hopeful about what this relationship could be. Don't rush it and don't force it. And you'll know if it's right. Like if your kind of experience looks similar to the story I gave you earlier, it's not right. And if it looks something along those lines, like you don't have to force this. You don't have to make it happen.

Like in my story of early flirting, like I knew it wasn't right, but I decided to just kind of keep on keeping on anyway, for some reason or another. And it won't always be as blatant as that, but you will know if it's coming naturally. And if the person is interested and excited to talk to you, like you will know, like a big question or that in this and like the one of the biggest kind of intimidation factors is like, what if they don't like me or what if they don't want to be talking to me? Like you will know you will.

Genuinely know if the person is interested if they're nodding along if they're laughing if they touch your arm if they're asking you questions back if They're smiling like all of the things that I'm saying if their body language isn't like slouched or crossed arms They're looking at their friend looking at their phone like every piece of advice that I gave you to go into flirting if they are also giving that energy back you will know that they are interested

And like when the feeling is not like trying to open a bottle that won't open and you keep trying and you're like squeezing and you put it between your legs and you're like, I want this open like, know that feeling. If that is what the flirting feels like, then you need to go on to the next one. Like this is not the person for you. You're not the person for them. It's probably their loss at end of the day. But like you will find something better for you. You don't have to keep trying to open that bottle.

And you can expect to get it right on the first time. Like you can expect this to just come so easily and be smooth sailing the first time you go up to somebody. Like you do have to kind of experience these trial and error periods or experience these times that on surface like are embarrassing of getting rejected or feeling like you got rejected. That is part of what it takes to kind of like develop the armor around this or develop the mindset and the confidence that like

Josh Felgoise (29:44.89)

You are comfortable going up to somebody and saying hi and introducing yourself and flirting in general. And when it doesn't go right, you can't let it take you off your course so much that you feel like it is completely on you and you let it take you down so hard. Try your best to not do that when you get rejected or when it doesn't work out.

Because you don't know this person at end of the day. They don't owe you anything, you don't owe them anything. Because not everybody is going to like you and not everybody is going to be interested in you and that is perfectly alright. Because at the same time, you don't like everybody and you're not interested in everybody, so how can you expect them to be, you know? Flirting is exciting. It's thrilling. It's goosebumps. It's something that we chase, that we don't always get to experience.

Think about it that way, reframe it in that way. Try to make this an exciting thing, an opportunity, a new thing that you get to go do, something that you are looking forward to and excited about. There's no mountain to climb, there's no hill to traverse. This is something that we get to do, that we want to ultimately do. Take the immense amount of pressure that we put upon ourselves off yourself.

Put the weight of making every interaction work down. They're not all going to work. And your expectation that they will all work is holding you back from finding the right one. Well, that was good. Let yourself try. Let yourself fail and let yourself flirt. It's fun. It's supposed to be fun. It is an experience. It's an opportunity.

It's not a trauma or a tragedy if it doesn't work out because eventually it will. Eventually you will find the right one. Eventually you will find the flight attendant to your pilot and she'll come up to the cockpit. No, but in all seriousness, like we we try to make every interaction work and when it's not, let it go.

Josh Felgoise (31:55.76)

Not every interaction is gonna be perfect. You're gonna be awkward. You're gonna stumble. You're gonna feel like you fell on your face. And it is important that you don't stay flat on the floor. It's important that you get back up and you go talk to somebody else and you put yourself back out there and you try again. That is the only way to develop confidence around this and that is the only way to get better at flirting.

That is the episode. you so much listening to Guy's Set, a guy's guide to what should be talked about. I'm Josh, I'm 25 years old and I'm here every single week, every single Tuesday to talk about what should be talked about for guys. If you liked this episode, I really hope you did. Please like, subscribe to this podcast. Five stars, maybe that's one, two, three, four, five stars, not four, not three, not two, not one, it's five stars. Thank you so much, I really, really appreciate that.

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