Ep. #38 Hacking Conversation Skills with Jon Sinn

[Jon Sinn]: Hey man, thanks for having me.

[Angel Donovan]: No problem. It's good to have you on here. I know you've been around a long time, haven't had a chance to connect, so it's good to finally connect up. Could you tell us just a couple of details about like where you're kind of living, hanging out, what’s your lifestyle right now, how old are you, to give like the guys a bit of perspective on where you're coming from?

[Jon Sinn]: Yeah, absolutely. So I'm 28, I’ll be 29 later this year.

[Angel Donovan]: Cool.

[Jon Sinn]: I live in Hollywood in Los Angeles about a few blocks away from the W Hotel, if people know where that is. What other stuff?

[Angel Donovan]: Cool. Well, how’s your dating lifestyle like these days? You know, everyone kind of has their own idea of what’s good for them. So how has yours kind of evolved over time and where it is at now? Are you in relationships, are you meeting different girls or, you know, what’s kind of where you at right now?

[Jon Sinn]: Yeah, so I'm kind of weird, like I'm not really a girlfriend type of guy.

[Angel Donovan]: Uh-huh.

[Jon Sinn]: So I'm seeing like four girls right now in LA, and I've been in this kind of noncommitted relationship with this girl I met in Florida who actually is like an up and coming porn star now for like five years. So, I mean, I hang out with her probably once a month…

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: And then I see the other four girls maybe like once a week or once every two weeks, and now I meet new girls on a regular basis, mostly through day game. I use some nighttime stuff because I'm fairly well-connected here in Hollywood…

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: …like a decent amount of my friends work in the nightclub industry. So I don’t generally go out so much to do pickup, but I go to parties that my friends like convince me to come to, mostly day parties I've been focusing on lately, like pool parties and like…

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: …there's this thing in LA called Fourteen on Sundays, which is like this kind of fancy day party where people like spray champagne and stuff. So I just kind of go to places like that. I don’t really do a ton of approaches these days outside of daytime.

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: At night, I generally just… there'll be a big table with a bunch of people who are trying to come over and like promoters, because they bring girls over and I just kind of meet girls who are brought over to me when I go to bars and clubs now. But yeah, I mean mostly day game for my approaches, and like I said, I'm seeing a few different girls, but nothing serious. I mean, the girl in Florida, it's been a long time, but we both… Sometimes she'll have a boyfriend, sometimes I’ll be busy, but it's just kind of a longer-term thing because I like her a lot.

[Angel Donovan]: Mm-hmm. Great, great. Yeah, we haven't had someone with that specific kind of relationship. Have you had a girlfriend before, a long-term relationship, or it’s kind of like where you come from…

[Jon Sinn]: I did, yeah, like three… Yeah. No, I've had like three long-term girlfriends in my life.

[Angel Donovan]: Yeah.

[Jon Sinn]: The last one was like a year and a half, and I actually lived with her, and she actually broke up with me and it was really bad, and that was when I like formally went off the girlfriend thing.

[Angel Donovan]: Right.

[Jon Sinn]: Yeah, because, I mean, I’d never really been into the girlfriend thing, like I always kind of wanted to be a player or whatever, and just kind of like… my ideas about atheism and monogamy were like both set when I was like 8 or 9 years old and they just didn't make sense to me, either of them.

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: So yeah, but I mean, there have been three times that I've been in relationships. The first was how I actually got in the pickup community. I was in a relationship with a girl for like two-and-a-half years, and the first nine months of it we didn't have sex because she was a virgin…

[Angel Donovan]: Okay.

[Jon Sinn]: …and she like… We broke up and she had sex with two other guys, and then I took her back and we still didn't have sex for like a year, like it was a really bad relationship. My second relationship was in San Diego with a really awesome girl who I just didn't treat very well because I was kind of learning pickup and being a player.

[Angel Donovan]: Right…

[Jon Sinn]: And then the third one was with a girl who really like I didn't think I was ever going to be in a relationship again till I met her, and then I was like totally in, and it just kind of was bad timing, very passive-aggressive both of us were in that relationship, and that's never good.

[Angel Donovan]: Yeah, I'm sure you learned something from it though. It's always interesting…

[Jon Sinn]: Oh yeah, you always learn some things like for sure.

[Angel Donovan]: Do you think you'll try the girlfriend thing again or you've kind of decided that…

[Jon Sinn]: I'm sure I will. I mean, I'm saying I won't right now, but I'm sure I will at some point.

[Angel Donovan]: Yeah. Cool, cool. Good. So how many women have you slept with so far roughly?

[Jon Sinn]: I stopped counting at 200. That was in 2009. So I don't know.

[Angel Donovan]: Yeah.

[Jon Sinn]: A lot.

[Angel Donovan]: Yeah. People pretty much always stop counting after a number like that. Okay, cool.

[Jon Sinn]: Yeah, I mean, I've had years where I've slept with 50 girls in a year. I mean, there were like… when I was really going out a lot and really especially like around 2009 when I was really working on the same nightly stuff, like yeah, it was a lot.

[Angel Donovan]: Excellent. Alright, cool. So there are a couple of things, like what we're going to talk about today is conversation skills. I know you've got a new program out on that, and just recently reviewed a couple of your programs on that, so wanted to do a deep dive on some of the things that we found that were interesting in those programs.

So, I mean, one of the main things like I pulled out of one of them is you go over… like a lot of guys, they have problems that they're talking to a girl for a while and then they run out of things to say. I think most guys have this problem. They draw a blank at some point. So in one of your products, you talk a bit about why you actually went out of things to say, and I thought that was interesting because like when guys kind of understand where the problem comes from, then it becomes something that they can work to resolve instead of it's kind of like, “I don't know why it happens to me all the time.”

[Jon Sinn]: Yeah, absolutely. I mean, I think running out of things to say is very universal. Everyone’s been there. You're talking to a girl, it's going well, and then, I call it hitting a wall, right? Like you're going, you're going, you're going, and then all of a sudden you hit this wall and you're just stuck, right? You either run out of things to say entirely or you start saying things that are really, really fucking stupid, right? When I used to teach bootcamps, so those were the two things I would see, you know, like especially with guys who were just getting started or guys who weren't very experienced or guys who weren't very good naturally with conversations, you know, and that's a lot of guys who find this stuff and are probably listening.

So what I've realized over years of teaching bootcamps, hundreds and hundreds of bootcamps, was that there are really four reasons guys run out of things to say. The first reason is they're not prepared, right? Now, that's where all the dating products and stuff really help you, because there's a lot of things out there on things to say, when to say this, when to say that, but you need to have some way to remember it when you're out in the real world.

And in addition to that, you need to know what subjects you're good at talking about. Like there are certain subjects that if I get on I can talk to women about and they will be super-interested in. There are other things that if I start talking to girls about they're not going to be that into it.

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: So you have to know what you're good at talking about and what you're not good at talking about.

And the second reason guys run out of things to say is that they get really nervous. And that's normal, like that's normal… it gets a little better when you've approached a lot of women, but there's always going to be some nervousness, especially depending on your level of anxiety as a person, right?

[Angel Donovan]: Mm-hmm. Mm-hmm.

[Jon Sinn]: Like some of us are higher-anxiety. I have probably higher anxiety than most people, so for me, that was my big problem when I started with women, was I would just get really nervous and run out of things to say. So you have to have some ways to deal with that.

The third thing is they get focused on saying the perfect thing. A lot of guys, they get kind of focused on this idea that there's one perfect thing or one perfect routine or one perfect kind of sequence that's going to unlock a door every single time, and that's not how human beings work, you know?

[Angel Donovan]: Yeah.

[Jon Sinn]: And if you're viewing girls as like this puzzle that you have to unlock or some sort of video game, you're missing a lot of chances to actually connect. So I think guys get focused on this idea that there's this perfect one thing that's going to make everything work.

And the last reason I think guys run out of things to say is they try to do too much. This is the guy who’s probably read a little too much pickup stuff without going out and actually trying stuff. So you get these guys—and I’ll give an example.

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: This guy came to a bootcamp in Vegas years and years and years ago, and he was a fairly older, you know, probably in his mid-40s, maybe 47, 48, very badly dressed, very socially awkward but bold. He was one of those guys who would do anything…

[Angel Donovan]: Mm-hmm. Yeah.

[Jon Sinn]: …but didn't understand why things were awkward…

[Angel Donovan]: Yeah.

[Jon Sinn]: So he would like walk up to a girl while she was with her boyfriend and go, “Hey, I thought you were beautiful and I wanted to meet you,” while she's holding hands with a guy.

[Angel Donovan]: [Laughs]

[Jon Sinn]: And he would think that that was good and that he was being direct and powerful and stating his intentions, and he didn't understand why the guy wanted to fight him. But there was some group of girls he was going up to and he was talking to them, and he was like asking them how they got to the place they were at like right after his opener. It was like, “Hey, how's it going? How'd you guys get here?” And obviously they were a little weirded out by that, especially from this guy who kind of looked like a serial killer.

And when I came over I was like, “What were you doing? Like why were you asking them how they got there?” And he's like, “Well, I was trying to get logistics for same-night lays for later.” You know, guys who read too much, because they haven't gone out and tried it, they think that they can like jam-pack everything in. It's like, if one technique’s good, if I can pack 50 techniques into 30 seconds of talking, then that's got to be perfect, and then the girl’s going to love me, right?

[Angel Donovan]: Right.

[Jon Sinn]: But again, that's misunderstanding how social interaction works.

[Angel Donovan]: Right. So like when you're trying to do something like that, there's no way you can really come across as normal because if you're packing…

[Jon Sinn]: Yeah, exactly.

[Angel Donovan]: ...even if you're really, really good, it's going to end up looking very strange.

[Jon Sinn]: Yeah, I mean, even for me, I can sometimes come across trying to do too much if I try to get too fancy. Like it's just… you've got to kind of take what the girl’s giving you. That's a big part of conversations in and of itself, is women are not as hard to read as we make it. It's just guys have what’s called the sexual perception bias. It's an actual thing where when guys are talking to girls, they tend to interpret anything the girl does as being a sign of sexual interest.

So girls are generally pretty clear if they're interested or not. It's just that guys want them to be interested. We don’t want to believe that the girl’s not interested, so we want to kind of tell ourselves, “Well, maybe if I do more stuff or I try harder, she'll like me.” But generally, that doesn’t work.

[Angel Donovan]: Cool.

[Jon Sinn]: So, [cough 00:12:09] excuse me…

[Angel Donovan]: Do you smoke?

[Jon Sinn]: But yeah, like basically those four things. Yeah, I do.

[Angel Donovan]: Okay. Noted. [Laughs]

[Jon Sinn]: That's where it comes from.

[Angel Donovan]: So yeah, man, I wanted to talk a bit about your third point, actually. You talked a bit about people being too focused on saying the right things, and I know what you're talking about there, but I think we could highlight that a bit more, like basically you're saying that things don’t have to be so perfect and that normal conversations aren't… It's not all that perfect. So could you give me like a rundown of like, you know, you, when you're out with a girl, like how much… do you think you make errors today or do things go wrong, and like how much stuff do you consider really good comes out of your mouth versus just normal stuff and everyday stuff?

[Jon Sinn]: Okay, so I guess I’ll just take those piece by piece. Right now I don’t use a whole lot of like routines…

[Angel Donovan]: Right.

[Jon Sinn]: …on a first meeting. On dates, I do have set stuff I want to get through, just because I have a very finely honed date routine now, where like if I get a girl on a date, like nine times out of 10 I sleep with the girl on the first date, like literal, like that's statistics…

[Angel Donovan]: Yeah.

[Jon Sinn]: Like I have kept that for the last two years. Like if I go on 10 dates, I sleep with nine of the girls. And so like I have a certain sequence I kind of want to go through. It doesn’t always come out the same way, but there's a certain kind of way I want to talk about my life on the first day.

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: On the first meeting, I'm kind of trying more to kind of fit to what I think she likes.

[Angel Donovan]: Okay.

[Jon Sinn]: So, for me, like I said, I'm 28, almost 29. The girls I tend to date tend to be like 18 to 22 or like 28 to 36.

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: So like I don’t really do good with girls who are like… I do good with girls who are my age and older, and I do good with girls who are significantly younger. I don’t really do as good with…

[Angel Donovan]: There's a gap there. Do you have any idea why that is?

[Jon Sinn]: There's a gap from about 23. Generally, I think that's when girls start to look for like marriage material, and girls realize I'm not marriage material very early on.

[Angel Donovan]: Oh. I guess girls of that age have a lot…

[Jon Sinn]: Yeah. So I mean…

[Angel Donovan]: …a lot going on in their lives, because actually that's a pattern that I would say my life has fitted into. There are a lot of girls like very early 20s for many years or…

[Jon Sinn]: Mm-hmm.

[Angel Donovan]: …it has to be a lot later, but there doesn’t seem to be much in the late 20s. Another reason I think it could be is because they start getting interested in work and they’ve got all this other stuff going on, you know. They're graduating…

[Jon Sinn]: I also think the early 20s, they haven't really met player-type guys yet or they’ve met guys who maybe aren't… don’t have as great game, so when they meet someone with pretty good game, it's like kind of a first. Whereas by the time they're like 22, 23, they’ve met that guy somewhere, you know. Probably wasn’t a pickup artist for most girls, but they’ve met some dude who like basically had them doing whatever he wanted and they're kind of like now weary of that. Whereas once they get over 28, then like they're either out of a broken engagement, divorced, or like you said, they were more focused on work for a long time, so now they're just kind of happy to get back out there and have fun.

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: I generally think that tends to be the pattern for a lot of people.

[Angel Donovan]: Yeah. Interesting, interesting. Okay. So, actually what I was getting at with your point is that like I think a lot of guys think that, you know, when they're talking to a girl, it all has to go like perfectly, but you know…

[Jon Sinn]: Right, yeah. I was going to get to that.

[Angel Donovan]: …if I think about what all the guys I know, you know, and even the really good guys who have been around for a long time doing it, a lot of the conversation is pretty normal, and then there are some things thrown in there…

[Jon Sinn]: Yeah.

[Angel Donovan]: …but a lot of it's just like we're talking right now.

[Jon Sinn]: Yeah, so when I think about kind of first day stuff, like meeting the girl, I kind of think in terms of waypoints, right? So I need some way to start the conversation. So girls browsing in a magazine rack, you know, at Barnes and Noble as I'm like walking in, I need some way to go over there and start the conversation. So I might walk over and pretend like I'm looking at what she's looking at and go, “Excuse me, I need to get to that,” and then when she goes, “Sorry,” which is what 99% of girls do, I go, “It's okay, I'm nicer than most people, so I’ll forgive you.” And now I've got a kind of funny interaction.

[Angel Donovan]: Right.

[Jon Sinn]: She'll laugh and I can now start a conversation. Or I might compliment something she has on. Or, if she's a little hotter, I might insult something she has on, because I find with a little bit hotter girls, if you compliment them, you get put into one category and you don’t get emotional responses, and they're kind of apathetic. So I might say something more ambiguous like, “That's a really weird like crystal thing you have there. Where’d you get that?”

[Angel Donovan]: Okay.

[Jon Sinn]: Or, ”That's kind of interesting.” And then like most hot girls will go, “Oh, thank you,” and I’ll go, “Oh, it wasn’t a compliment. I'm just curious about it.” So those are generally the ways I’ll start conversations during the daytime. [Cough 00:13:35] I just got back from Vegas. I smoked way too many cigarettes over the weekend.

But yeah, like basically, if it's at night in a bar, a club, I'm probably just going to say something more direct like, “Hey, my name’s Jon. I thought you were cute. I wanted to meet you.” Or, “Hey, I walked around this entire bar and I think you guys are the only girls cool enough to talk to.”

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: Kind of simple.

[Angel Donovan]: Okay.

[Jon Sinn]: Yeah. So do I make mistakes? Of course. Everybody makes mistakes. To me, cold approach pickup, especially the initial pickup part of it, is really a game of mistake correction, like you're going to make mistakes. There's no such thing as the perfect pickup. There's no such thing as like the million-dollar mouthpiece or whatever these stupid fucking guys who never get laid are talking about. There isn't. Everyone I know who's good with women makes mistakes and makes big mistakes. It's how they correct those mistakes that determines whether or not they get laid. So you're going to make mistakes. It's just how you cover up your mistakes that kind of determines things.

And then as far as how many things do I think are good that come out of my mouth, well, I'm a narcissist, so I think that everything I say is really funny, including jokes that repeatedly people don’t laugh at. Like I have a joke I tell about how the guy who first decided women should have the right to vote really fucked it up for everyone else. No one ever laughs at this joke, and I continue to bring it out in social occasions all the time because I think it's fucking hysterical.

So yeah, I mean, I'm a bad judge because I'm my biggest fan, or second biggest fan to that girl in Florida. But yeah, I mean, how much of it is actually good? Maybe 50%, maybe less. I don't know.

[Angel Donovan]: Good, yeah.

[Jon Sinn]: But I think it's all awesome. [Laughs] Yeah.

[Angel Donovan]: Alright then. Yeah, but it's good to give the guys… you know, shooting for perfect is really not worth doing here. It doesn’t really take any material this is…

[Jon Sinn]: Yeah, I mean like…

[Angel Donovan]: …supersonic special…

[Jon Sinn]: That's the thing I said about not running it, like not worrying about the perfect thing to say. Like I said, like I continually in mixed company, like with girls I'm like sleeping with, tell jokes that I know don’t hit and are kind of offensive, because I don't care because I know it doesn’t matter, you know? Like that's kind of the point. The point isn't that I'm like socially obtuse. Like I do it because it doesn’t matter, because I can say something stupid, I can say 10 stupid things when I'm picking up a girl and still get her into bed that night.

[Angel Donovan]: Right.

[Jon Sinn]: You know? It's all in how I recover it. And yeah, trying to shoot for perfection, trying to be too cool, those are two mistakes I think the pickup community really ruins guys with. Because the guys I know who are really good with women, they don’t try to be cool and aloof. Like Mystery with his whole like nagging shit and this whole like act like a rock star, like now that I actually have really good hookups, like the guys who get a lot of girls are kind of goofy.

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: Like they're goofy, they're party guys, they're fun. They're not really this like, “Oh, hands off the merchandise,” because no one wants to be around that asshole. That only works if you're actually famous and you actually bring some sort of like legitimate value to the interaction. Otherwise, you've got to be fun. And if you're fun, you can make mistakes.

[Angel Donovan]: Totally, totally, because it's not so serious either.

[Jon Sinn]: Right.

[Angel Donovan]: So like when you talked about routines, you referred to it a few times there, you said you may be using routines today still. Like when we're not talking about when we're talking about like improving your conversation skills and not running out of things to say, is it necessary to learn a bunch of routines to do that or is it even a good idea to learn a bunch of routines if you have this problem?

[Jon Sinn]: It's not necessary, definitely not. It's definitely not necessary. It can be helpful though. So I’ll give my little routine spiel here.

[Angel Donovan]: Okay.

[Jon Sinn]: Because I've been on both sides of this argument, like this was like a huge thing for—I don't know if still is. I'm not as on the pickup boards as I once was. But this was like a big thing in like ’07-’08, right? It was like, routines are the best because they get a specific response every time. And then it was like, not routines are the best because then you can really connect with people. And there are pros and cons for both.

So, basically, it kind of comes down to the type of dude you are. If you're the type of dude who finds it really hard to talk to people, you know, like I have a good friend like this. He's just like tough to talk to. For him to go out and start approaching people, it's going to be tough unless he gets some routines, you know?

[Angel Donovan]: Uh-huh.

[Jon Sinn]: If this is you, if you have trouble, if you don’t have that many friends or if the friends you do have like always have to like ask you a bunch of questions and you like… you're not Mr. Talkative, then routines are good because at least give you something to say if you don’t have something you want to say in and of yourself. That wasn’t really my problem. I wasn’t that guy as much as I was like I didn't realize what I could and couldn't say with women.

Now, on the other hand, the problem with routines is they're not magic and they're kind of restrictive. When I say they're not magic, I mean there's nothing that makes… Guys all like say these routines… When I used to teach bootcamps, there’d be dudes who would be running routines like the C versus U smile or like some other routine they read on the Internet, and it would never get a good reaction for them. Horse girl, the Brad P opener, is the worst offender. And I like Brad P’s stuff a lot, but that opener is really hard to use for most guys.

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: And you know, they'd be running this 50, a hundred times, and every single time the girl would have a bad reaction, and I’d be like, “Why are you using that routine?” They'd be like, “Well, I heard it's a good routine.” And I'm like, “Well, dude, how many times have you done it?” And they'd be like, “I don't know, like 300 times.” And I'm like, “Has it ever gotten you a good reaction?” They'd be like, “No.” I'm like, “Well, clearly it's time to stop,” you know?

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: Like that's the thing with routines. Not every routine is going to work for everybody. Some routines are more, you know, towards a guy who's kind of like Mystery, like that threes versus sevens routine. Like if you get like kind of a 19-year-old frat party guy and he's doing that at like some frat or college party, he's going to be weirding, creeping chicks out, right? Whereas when Mystery does it and he's dressed all weird, then it kind of makes sense, and he talks about how he's a magician.

On the other hand, like a routine like best friends test or kind of stuff like that, that's kind of more club funny. Some of the role-plays that are out there, some of the cocky funny stuff, if you're a 48-year-old man talking to a 36-year-old woman in like a hotel lounge, that's going to be weird too.

So these routines are not designed for everybody. They're designed kind of to fit certain people’s personalities, generally the people who came up with them. So a lot of guys are not good at course-correcting with routines, which means they just use them kind of without noticing whether or not they're working.

And they're also kind of restrictive, and they also get boring, you know? Like the big end for me with routines was my routines stopped kind of working for me, because I was just so bored of telling them that I was just like, I’d be like cutting myself off. I’d be like, “This is stupid.” Like I’d like rush through stories and like miss the good parts because I just wanted to get it over with. I’d feel weird like I was some actor reciting cheesy lines. That was kind of the end for me of a lot of routines.

So to me, I mean, you want to kind of move in terms of themes, like there are always going to be themes that I talk about with women, there are always going to be subjects that have come up.

[Angel Donovan]: Right.

[Jon Sinn]: You're always going to talk about your history as a person. You're always going to talk about kind of past relationships, college, work, things you're interested in, [cough 00:25:42] etc., etc.

[Angel Donovan]: Yeah, I like the idea of moving towards themes versus routines. Of course, like some guys are going to find routines helpful to, you know, combat nerves and stuff, or as you say, in cases where it can help a bit. But I'm sure it also contributes to this running out of things to say because they memorize a couple of routines, and then once they’ve done them maybe they remember they’ve heard the routine, you know. It's just this kind of pressure of having memorized stuff in the bag and thinking you're going to have to use more of it, or getting in that mode of kind of recite… I don't know if you've seen this before, but if someone’s kind of reciting their routine, they're kind of in that mode of using their memory, right? Versus just getting in that mode of socializing. And in some ways it can be maybe kind of difficult to make a switch in the middle of the conversation.

[Jon Sinn]: Yeah, I mean, there's definitely that, you know. No one has… No one besides Mystery has seven hours of routines memorized, you know? And the other thing is it's hard to access a lot of that stuff, so a lot of guys who like study routines and the moment they can't remember their routines, like you said…

[Angel Donovan]: Yeah.

[Jon Sinn]: …and then they're screwed anyway because they were so reliant on it. That's what I said. You don’t want to be reliant on them. Like the best attitude towards routines to me is not to like look at them like they're some sort of horrible thing like, “Oh my God, I have to avoid routines,” but you just don’t want to be reliant on them. You can use them if they are appropriate and they fit and they work for you, but you don’t need to, you know?

Like there are some times where something comes up… Like I have a bunch of tattoos, and like I have a bunch of like… I don’t even know if they're routines in the real life anymore at this point, I mean, and they did happen to me but I tell them the exact same way every time. See? Like that's where life blurs, right? Like, are my stories about my tattoos a routine? But they're real. Who knows? But sometimes I just don’t feel like telling the story, so I'm just like, “Oh, I’ll tell you some other time,” or “They don’t have any meaning at all, I just think they're pretty,” you know?

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: So it's kind of one of those things, like you don’t always have to use them even though they're there. But yeah, I mean, you don’t want to be one of those people who’s like, “I never use routines,” either, because there are places where routines are useful. And I mentioned a while back waypoints, basically starting the conversation, that's a good place to have a routine.

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: Breaking social comfort – after you start a conversation you've got to make people socially comfortable. This is one of the big reasons guys who study pickup fail, is because they try to jump from opening to starting attraction, especially with nags, teasers, etc. But you can't tease or break rapport with someone who doesn’t want to talk to you yet. And a lot of the times in real life, when you start a conversation with a girl the first 10 seconds, especially with those openers I shared earlier, which are very short, the girl hasn’t made a decision on whether or not she wants to talk to you yet. So if I start breaking rapport with her right away, unless she's like a very hot specific type of girl who is like a polarity responder, which is like the girls that I would open with those kind of quasi-insults…

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: But you know, I've been doing this for like 10 years, so I can tell which girls those are and which girls they're not. They're not all hot girls. But for the most part you want to build that social comfort before you break it, but you should have a go-to way of breaking social comfort, you know?

[Angel Donovan]: Okay, can we take like a step back to kind of…

[Jon Sinn]: Sure.

[Angel Donovan]: …the beginning of the conversation and just work our way through, and then like I think the guys will kind of get it a bit easier.

[Jon Sinn]: Sure.

[Angel Donovan]: Because you've just brought out a lot of topics.

[Jon Sinn]: Yes.

[Angel Donovan]: So, first of all, like when you want to start a conversation with a girl, what you said, like you said it's useful to have a couple of basically default things to say…

[Jon Sinn]: Yeah.

[Angel Donovan]: …or when you start talking to a girl. So could you give some examples and why you would do something like that?

[Jon Sinn]: You basically want to have two default things. Sure. You basically want to have two default things. You want to have a thing to say when a girl’s by herself and a thing to say when a girl’s in a group.

[Angel Donovan]: Okay. Makes sense.

[Jon Sinn]: Right? So for me, like I said earlier, daytime I like that “excuse me, like make the girl apologize and move, and then tell her I forgive her” opener. I use that a lot. I also just use, “Hey, I really like x item about you,” usually tattoos or fashion sense.

[Jon Sinn]: I don’t really do full direct. I find that the results with full direct are bad. Maybe I'm not good-looking enough, I don't know, but for me, when I go full on “I thought you were really attractive” or “I thought you were beautiful” or “cute,” I get a much worse response than if I go “I like something about you.” So for me that works better.

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: That’s just kind of my own testing, you know?

[Angel Donovan]: Right. So for that, all you have to do is be observational, right? When you see the girl, you notice something about her that you can talk about, and you go in.

[Jon Sinn]: And also like remember how I talk about how I like specific types of girls? Like one of the key things if you want to get really good at pickup is you have to figure out your demographic, right? So like, for me, a lot of the time it’s tattoos, because I really like girls with tattoos. Like I haven't dated a girl who doesn’t have tattoos in a really long time.

[Angel Donovan]: Fortunate to be in LA then.

[Jon Sinn]: Yeah, for sure. For sure. And especially Hollywood. But yeah, so I mean, for me like I’ll generally open with something like, “Hey, excuse me, I know this is really random, I really like your tattoo. Did you get it done in LA?” And then she'll say yes, no, whatever, and from there I'm just going to kind of talk about tattoos. I'm going to wait to see if she asks me about my tattoos, because that's like the big buying signal I look for. If a girl asks me like what my tattoos are, then like she's hundred percent interested and attracted.

So if that doesn’t happen, I'm just kind of trying to kind of talk, be funny, not be too direct or aggressive, and basically let her get comfortable. Because especially in the daytime, women aren't used to being approached, so it takes them a little longer to get comfortable being conversational, you know? When you just instantly approach and make them make a yes or no decision about whether or not they're attracted to you…

[Angel Donovan]: Right.

[Jon Sinn]: …they're literally just going to go on looks.

[Angel Donovan]: Yeah.

[Jon Sinn]: That's it. Like that's what you're forcing them to make. And like, I mean, it's funny because I've been on both sides of the coin now. I've had… in the beginning of my pickup career, everyone was saying I was good-looking and that was why I was getting results, and now on boards people make fun of my looks and say I look Iranian and Jewish. So I don't know if I'm good-looking or not. I know I'm about a… I know when I go direct, the best I do is about 7… like I do the best with around 7’s, which probably means I'm around a 7, because with the direct approach you're basically doing basically… You're basically just playing the numbers game based on looks, which is cool. I mean, that is a way of getting laid. But it's not particularly helpful for guys who aren't that good-looking, and it's not particularly skillful.

So, tattoo talk or whatever. Or, you know, I’ll make some observation… like a lot of times I make observation teases, like I’ll open with teases. Like if a girl is like studying in a bookstore, I’ll say something like, “Excuse me, you're really concentrating hard and it's really distracting to like me sitting here and playing games on my cell phone, so could you like take it down a notch? Thanks.” And then, you know, either the girl will laugh and get it or she'll give me like a death stare or she'll like close her books and leave, you know?

[Angel Donovan]: Okay.

[Jon Sinn]: One way or the other. I'm big on openers that are going to polarize, because I feel like when you're doing cold approach you either want a girl who's kind of instantly in or instantly out.

[Angel Donovan]: Right, that's a not wasting time kind of thing.

[Jon Sinn]: Yeah, but you just don’t want them to make that decision based on looks, right?

[Angel Donovan]: Right, right.

[Jon Sinn]: Like I think a lot of guys equate that to direct approach, and they go, “Well, direct approach, you're like making them make a yes or no decision.” Yeah, you are, but you're making them make that on looks because you're not really giving them any personality.

[Angel Donovan]: Right, right.

[Jon Sinn]: Whereas like saying something funny and kind of quirky, like that gives a girl a chance to go, “Okay, like I’ll give this guy a chance,” as opposed to just, “I thought you were hot and I wanted to talk to you. I'm a dude, I've got a dick.”

[Angel Donovan]: Right, right. Okay, so say she's just like responding normally, nothing special.

[Jon Sinn]: Yeah.

[Angel Donovan]: She's not checking out your tattoos or anything like that.

[Jon Sinn]: Right.

[Angel Donovan]: After your observation she's just like, “Yeah.”

[Jon Sinn]: Yeah. So I'm just going to kind of start leading conversation and grounding talking about myself, you know?

[Angel Donovan]: Okay. How do you transition to that? Like do you just start talking about something new or…?

[Jon Sinn]: Well, there are a lot of ways to transition, right? I could ask a followup question, right? I could say like, “What are you doing at the mall today, shoe shopping?” And then she'll say, “Yeah, just shopping,” or like she's just giving me one-word responses or whatever…

[Angel Donovan]: Yeah.

[Jon Sinn]: And I’ll go, “That's cool. I actually live right across the street, so when people aren't willing to come meet me like at my house, I'm willing to compromise by going two blocks,” right? I'm just doing things to kind of be funny, not displaying interest, but talking about myself. And then I’ll go, “Yeah, it's really cool that I work for myself, so I thought I’d get out of the house. It's a really nice day.”

And now I'm going to start to kind of do a little bit of kind of slight cold reading about her, not cold reading like, “You're lonely and you meet guys who aren't into you,” but kind of things like… You know, like I live in LA. So, most people aren't from LA. So at some point after I've talked about myself a little, because I'm always going to ground myself first, right?

[Angel Donovan]: Okay. So wait, wait, wait… So going back, so what you did when you transitioned there is you asked her a question about what you were going to talk about?

[Jon Sinn]: Right, exactly. Yeah.

[Angel Donovan]: And then you went on talking about it, which is some subject that actually you're interested in talking about, right?

[Jon Sinn]: Yeah, I mean, also just basic information. Like the thing about grounding… grounding is a topic I talk about a lot.

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: When you talk about persuasion, there's a principle that's really interesting called reciprocity.

[Angel Donovan]: Right.

[Jon Sinn]: And Robert Cialdini talks about it a lot. And the idea of reciprocity is that people are more willing to do things or give you things if you give them things first. Well, the same thing occurs with exchanging information. If I ask a girl what she's doing and she's kind of giving me mediocre responses, she's going to give me a one-word response. But when I give her more information, the next time I ask her a question, she's going to now feel that reciprocity and she's going to want to give me more information on the next question.

That's one of the reasons that just asking girls questions and giving one-word responses doesn’t work. Like the way most guys ask questions is they don’t use it to lead a conversation like I do. They go, “Oh, so what are you doing here?” And she goes, “Shopping.” And they go, “Cool. Where are you from?” And then they just ask another question and another question, but the girl’s not getting any information back. She's just getting asked for information. And it violates that role of reciprocity, and the girl eventually is just like, “This is annoying. Go away.”

[Angel Donovan]: Right, right.

[Jon Sinn]: So I want to always use my questions to either lead, tease or to kind of tell a story, you know? So I’ll say, “What are you up to today?” “Shoe shopping.” And then I’ll go on about what I'm doing and kind of ground myself a little bit, you know?

[Angel Donovan]: Right.

[Jon Sinn]: I’ll go, “Yeah, you know, I have my own business. I get to set my own hours. It's really cool.” And then I’ll talk about like who I'm meeting, because I'm usually meeting people. Like I’ll be like, “Yeah, my friend Chanel, she works over at such and such,” and I’ll just kind of talk about my friend. I'm just kind of grounding myself as a person, right? I'm making myself more of a real person, giving her information about me without kind of trying to brag, without trying to “DHV,” without giving her like a lot of interest on her. I'm just kind of talking… It's more just like I'm a social, talkative person.

[Angel Donovan]: Yeah.

[Jon Sinn]: And then I want to eventually start testing to see if she's interested, and what'll is she'll start kind of talking back more once you do that, usually in like three to five minutes.

[Angel Donovan]: Okay, great. So basically you said that questions, I mean, normally like you hear a lot of advice that says don’t use questions, but…

[Jon Sinn]: Yeah.

[Angel Donovan]: …you said that in a few specific areas, if you use them properly, questions can be pretty useful, right?

[Jon Sinn]: Absolutely.

[Angel Donovan]: So it's leading into a new topic as you did when you said…

[Jon Sinn]: Yup.

[Angel Donovan]: …you know, “Are you shopping?” You asked her a question and you start talking about that. So it's kind of like an intro. It's like getting her to perk her ears and listen up.

[Jon Sinn]: Yeah.

[Angel Donovan]: And you said tease and telling a story. So those are kind of… using a question, you're setting up the tease?

[Jon Sinn]: Yeah.

[Angel Donovan]: Like that?

[Jon Sinn]: No, so I mean, like if I go like, “What are you doing here today?” and she says, “Oh, I'm just shopping,” I can go, “Let me guess. You need to get a new outfit for your new nighttime job as a naughty nurse,” right?

[Angel Donovan]: Right, right.

[Jon Sinn]: That's what it is.

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: I figure it out, right? Or I’ll go, “Let me guess. You're down to like five Justin Bieber CDs in your car and you want to make sure you have at least…” right?

[Angel Donovan]: Yeah.

[Jon Sinn]: Then I'm just going to tease her about whatever she's shopping for, you know.

[Angel Donovan]: Cool. So you know, basically, the rule is kind of like… it sounded like to me, is like as long as you're using a question with other content, you're saying other things, then it's fine.

[Jon Sinn]: Yeah. Yeah. The problem is just what most guys do is they rapid-fire questions without using them for any reason. They're just asking questions to kind of tread water and keep the conversation going.

[Angel Donovan]: Right. Cool. So once you've got her talking to you, like you consider you've got to some kind of waypoint or something, and then you start changing the subject?

[Jon Sinn]: Right. I mean, subjects change throughout social comfort.

[Angel Donovan]: Yeah.

[Jon Sinn]: Like subjects are like kind of a constantly changing thing. I mean, I always thought it was funny when guys would kind of be like, “Then I talk about this, then I talk about this.” I mean, conversation’s kind of ping-pong, you know?

[Angel Donovan]: Right.

[Jon Sinn]: You've got to be able to kind of go with the flow in terms of conversation. But basically, I'm definitely trying to keep the conversation mostly on the topic of me. That's like a big mistake a lot of guys make, is they feel like they shouldn't talk about themselves, but they should like ask the girl about herself. Like you approached her. She didn't approach you. So the burden of keeping the conversation interesting and fun is on me, and the burden of showing this girl that I'm cool enough for her is also on me. So I have to do that.

But I don’t need to do it super-hard. I don’t need to really start DHVing and kind of bragging. I just call DHVing bragging, for those of you who like DHVing. Just consider every time I say bragging, consider that DHVing. I don’t like to do that until I've got some interest, because if you brag too early it can turn girls off, or it can make you seem like you're kind of overly arrogant or you're just kind of lame.

So, basically, let's say she starts kind of warming up, you know, I do a little bit of cold reading. Like I was saying earlier, like I live in LA, so like most girls aren't from here, so I’ll go, “Alright, you're not an LA girl. Where are you originally from?” right?

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: That's like I'm asking where are you from but I don’t even have to add the “where are you from” part. I just go, “You're not an LA girl.” And they go, “How do you know?” And that's like a little cold read.

I could also say, “You're like an East Coast girl,” or “You're like a Southern girl,” you know. Wherever you're at in the country or the world, you can use whatever the other part of a country is to kind of cold read that. And that's a good thing to do because if you get it right, the girl will think you're like really cool, and if you don’t get it right she'll want to know why you thought that about her, and that gives you an opportunity to tease, it gives you an opportunity to tell a story about a girl from there, it gives you an opportunity to talk about traveling. I mean, there's just a lot of good that comes out of stuff like that.

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: But once she's kind of engaged, once she's asking me questions, and again, like all this stuff is not rocket science, you know? Like it's just dudes don’t want to believe that girls aren't into them. If you're not getting any signals after five to 10 minutes of conversation, that girl’s not into you, just point-blank period, and you should bail.

[Angel Donovan]: Okay.

[Jon Sinn]: But, you know, if she's asking you questions, she at least asks what your name is, she giggles at some of your jokes… and you should be mixing touching in with this too, because touching is the ultimate way to see how she's reacting. Like if the girl’s kind of giving me one-word answers but she's like letting me touch her and she's like letting me get close to her, then I don’t give a fuck what she's saying because nonverbally she's telling me she likes me, you know?

But let's say she's accepting the touching but she's not super into it, maybe as I grabbed her arm, which is something I like to do early on in day game, she like took a step backwards, but she's still talking to me and flirting, now I'm going to start to tease her, and that's to break the social comfort. Because like I said earlier, you can't tease someone who doesn’t want to talk to you, but once someone does want to talk to you, then teasing them becomes very effective, because now you've got a little bit of rapport and comfort, and when you break it it's going to be more powerful.

So I may say something like, “Oh my God, you're such a pain in the ass. Your last boyfriend, like he must be up for sainthood.” Or I’ll say something like, “You know, your last boyfriend clearly doesn’t spank you enough.” I like saying something about a boyfriend/other ex-boyfriend because I want her to say, “I don’t have a boyfriend.” Like especially during day game, I want her to tell me if she has a boyfriend or not really early on because I think girls will waste a lot more of your time during the day and then tell you they have a boyfriend like 20 minutes in, than at night where boyfriends generally don’t exist as much. So it's important that you like kind of get that out of the way early.

But otherwise I’ll just go, “You're such a pain in the ass. God,” like any tease, just something that breaks the social comfort. Now I've switched to teasing her a little bit, she's going to react to that, and what’s going to happen is she's going to now get emotionally invested. That's just a way to kind of spike her emotions and get what I like to call emotional fluidity. Because the opposite of love is not hate, it's apathy, and apathy is really the enemy of the approach. That's the only reason you need to tease, nag, etc. If the girl’s already into you and like emotionally fluid, she's laughing, she's like going through different emotions with you, then the tease is kind of irrelevant. But it's just a very consistent way to ping a girl and get an emotional reaction. But that's the only reason it exists. There's no magic in teasing or insulting girls. It's just one of many ways to get an emotional reaction. It's just a very consistent way of doing it.

[Angel Donovan]: Okay, okay. Well, so say it was going all well, right?

[Jon Sinn]: Right.

[Angel Donovan]: So she's getting engaged with you and everything, but then you just kind of draw a blank, right?

[Jon Sinn]: Mm-hmm.

[Angel Donovan]: For maybe one of the reasons that we talked about earlier. What are ways to get out of that quickly? What kind of tools do you have?

[Jon Sinn]: Okay, so I’ll give you my best tool for this. There are a lot of different ways to get out of it, but the best way is through creating an acronym, and it's really, really simple. You're basically going to create an acronym of your good conversational subject. So, basically, like I said before, guys have to be prepared. So you have to know what you're good at talking about. For me, it's psychology, traveling, relationships, TV and movies, and I'm missing one… and yoga. There you go. So PT and Y, whatever, PTTY. I basically have an acronym. So whenever I've run out of things to say, I just think of those letters, and those give me my good conversational subjects, right? And that's really the best way for guys to not run out of things to say.

But there are a couple of other things you can do. You can use your environment. Try to focus on like people, things, like settings that you can use to talk about in the environment. One thing I do a lot is people watching. I’ll say, “You know, I'm such a people watcher.” Like if I run out of things to say, I’ll go, “I'm a really big people watcher, but I always make really mean comments in my head,” and then I’ll just make fun of someone in the immediate area. That's a good kind of way to use your environment.

[Angel Donovan]: Okay, yeah.

[Jon Sinn]: And you can also kind of just talk about things you care about, you know, or whatever comes into your head at that moment, you know? It may not be the best subject, but sometimes if it's all you've got, go with it.

[Angel Donovan]: Right. Saying something is nearly always better than…

[Jon Sinn]: Always better than saying nothing.

[Angel Donovan]: Right, right.

[Jon Sinn]: We know a hundred percent of the time that standing there in silence does not get you laid. So anything you can do besides that has a better chance.

[Angel Donovan]: Right. So going back to those topics you chose, like I guess these are topics you know pretty well, right? And you're interested in.

[Jon Sinn]: Yes.

[Angel Donovan]: But how would you… Like once you've got that like acronym, so you know what they are, how do you pick something out of your brain? Do you just kind of think like, so you said relationships, for example, do I think, “Okay, relationships…”

[Jon Sinn]: Right. So if I say relationships, then I just start thinking about relationships and looking for ways to tie it in. So I may say something like, “You know, you really remind me of my friend Kim,” and then I’ll talk about my friend Kim and my relationship with her or her relationship with like her boyfriend.

[Angel Donovan]: Actually…

[Jon Sinn]: Or, if I think like psychology…

[Angel Donovan]: Right. So, I mean, really there are probably simple ways you can integrate like any topic, you know, three or four ways, whatever, like you just did, you said, “You remind me of my friend Kim,” right? So you just said, “Oh, you remind me of…”

[Jon Sinn]: Yeah, I mean, that's just transition, right? Like that just comes down to the skill of transitioning, which is useful in two places. It's useful for getting off your opener. That's where most people use it, right?

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: But it's also useful for just switching conversations anytime, you know? Like sometimes you hit conversations that are like bombs, right? Like there was a time I was talking to this girl and I was like, “Oh, you picked an interesting finger to wear your ring on. That's cool.” And she's like, “Oh yeah, my brother gave me that ring before he went to Iraq. We just found out he died two weeks ago.” And I was like holy shit, I just opened up a terrible can of worms.

[Angel Donovan]: Right.

[Jon Sinn]: [Cough 00:48:02] So I had to transition to something else, you know? So transitioning, there are a lot of ways to transition. You can…

[Angel Donovan]: Well, that goes back to, you know, earlier you were talking about how a lot of meeting women and things going well with them is recovering from mistakes.

[Jon Sinn]: Yeah.

[Angel Donovan]: So a transition, like these transitions are really useful because it's basically this kind of default phrase, you start to go into another subject whenever something goes wrong.

[Jon Sinn]: Yeah. I wouldn't say a default phrase, more like a default set of skills, right?

[Angel Donovan]: Okay.

[Jon Sinn]: Because there are some times like with the dead fucking brother ring, I couldn't just go, “Anyway…” you know?

[Angel Donovan]: [Laughs]

[Jon Sinn]: Or, “That reminds me of…”

[Angel Donovan]: Right.

[Jon Sinn]: That wasn’t going to help me, you know? There I had to kind of back out gracefully, and then change the subject, you know?

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: But yeah, like transitioning is great because it kind of always allows you a way to kind of get off of one topic onto another as well as to move the conversation forward. Sometimes you get stuck talking on things, and while it's a good conversation and you're like building rapport and the girl likes you a lot, it's not really moving things in a sexual direction.

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: So yeah, I mean there are a lot of ways to transition. You can transition with a phrase like “that reminds me,” “that's just like when,” “you remind me of,” “check this out,” “I gotta to tell you about,” “oh my God, this is crazy,” stuff like that. You can transition with an observation. I do that a lot. You can transition with a role-play. You can transition with a question provided you follow it up with something. Early on, you can transition with an introduction. And there are probably seven or eight more in the effortless conversation system, but those are kind of good starting points right there for how to kind of move from subject to subject.

[Angel Donovan]: Great. And so you were talking about this acronym with subjects. For you personally, I mean when you're advising students, do you kind of advise them to think of like five topics they're going to talk about in each of those subjects so they can probably remember them or do you just tell them to focus on those subjects and kind of run with it?

[Jon Sinn]: I tell them to focus on the subjects and run with it.

[Angel Donovan]: Okay.

[Jon Sinn]: I tend to find, for myself and my students, the best material gets made up in-field. So if a guy wants to talk about psychology, go out talk about psychology, the thing that works best when you say something that a girl responds to, you know, make a mental note to try to say that again and see if it works again. And that's kind of how you build your conversational repertoire, you know, so to speak…

[Angel Donovan]: Right.

[Jon Sinn]: …is these little anecdotes. Like most of my things are like little anecdotes I said once that someone laughed at that then I just kept saying.

[Angel Donovan]: Yeah.

[Jon Sinn]: Like a good example is like anytime a girl gets up or is like, “I’ll be right back,” I’ll be like, “I’ll be here. I’ll be the guy who looks like me.” I said that one time, the girl laughed, and like now I say it every time and girls and people always laugh when I say it, like in any context.

[Angel Donovan]: Right, right.

[Jon Sinn]: So that's like a little thing that just came up because I was making a joke one time and people thought it was funny.

[Angel Donovan]: Right, right, right. And what you just said is what everyone I know who’s good does, right?

[Jon Sinn]: Yeah.

[Angel Donovan]: If they’ve been in this for a while, you can't help but just build up these natural… I mean, this is what we did for other areas like business or whatever else, you know. Other facets of our life, we do the same thing, right? We have set stories and phrases and ideas or whatever that come up and we repeat them, and when they work with repeat them again. So you're saying that basically we do that a lot in dating. So it really puts it down to experience is really, really important, getting out there and getting more experience, because material when you need it will just come to you because you picked up so much all the time.

[Jon Sinn]: Yeah, I mean there's no substitute for experience in this. Like you have to get out there and take action and you have to start approaching, and you have to do it a lot.

[Angel Donovan]: Right, right.

[Jon Sinn]: And you know, it's not good enough to do it once a week or do 20 approaches in one night.

[Angel Donovan]: Right.

[Jon Sinn]: Like you have to kind of do it on a regular basis so that you become more of a social person and more of a kind of open person, because I think a lot of the guys who have dating problems, a lot of it's because they're very closed off and defensive. I know that was a big problem for me, and I didn't really… Like I got success with women before I fixed that, but I didn't really get total social success until I fixed that.

[Angel Donovan]: Yeah.

[Jon Sinn]: So yeah, I mean, I think…

[Angel Donovan]: Well, yeah, I think it's interesting, you know, the whole subject thing is you're telling them to choose subjects that they know well that they feel comfortable with, and in a way they’ve probably built up a bunch of things that they say in those subjects, right? They're really things that they like talking about, and there's a bunch of stuff that they can already basically grab.

[Jon Sinn]: Yeah.

[Angel Donovan]: And also I think maybe, I don't know if you've thought about this before, but when we like something, you know, or when there's something that we're into at the moment, maybe it's a particular diet or whatever it is, right? We have a habit of like thinking about it more and linking it into conversations.

[Jon Sinn]: Yeah.

[Angel Donovan]: So I’ll be talking to a friend about whatever, TV, whatever, and the paleo diet comes into our head and we link it to the paleo diet, and that's something I think people do naturally.

[Jon Sinn]: For sure.

[Angel Donovan]: So you giving them these four subjects that they know well, it's something a lot easier for them to branch out and run with because it's something that you naturally do anyway.

[Jon Sinn]: Yeah, for sure. And I also think another part of it is it's also teaching them to fish rather than giving them a fish, right? Like if I just gave them like five routines they could use whenever there was a dead silence, then they just become dependent on those routines. But if you give them four subjects, they have to actually actively engage and actively think, “Okay, how am I going to get this conversation back to the subject here?” you know?

[Angel Donovan]: Yeah.

[Jon Sinn]: And it forces them to kind of problem-solve in real time, and I think that's a lot of socializing. Like I'm really into sneaking in places.

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: Like now that I have friends in Hollywood, like I basically made those friends because I kept getting into their parties through like backdoors and shit like that, and they were like, “You're never on list. How are you always in here?” And I was like, “Don’t worry about it.” But like to me, that gives me a kick, right? So that's like real-time problem-solving, you know?

Like a couple of weekends ago we were trying to sneak into the Roosevelt Pool Party, and the way we normally go, the door was locked, but I saw the maids on the other side, so I just knocked and like told them we had locked ourselves out of the room, and they let us back in, you know? Like that to me was like the apex of like my pickup and my social skills, is like we basically were caught in a situation we weren't supposed to be in, and I was able to talk someone into helping us when they shouldn't have.

[Angel Donovan]: Right.

[Jon Sinn]: And I think pickup is very much like that in that you're going to have to… It's not an autopilot sport, right? Like it's not something where you just kind of, like it's not driving. Like they always make the driving metaphor, and like it's not driving, because I can zone the fuck out when I'm driving and end up somewhere and not know how I got there, you know? You can't zone out with pickup. Like you have to be pretty quick in paying attention to what’s happening because otherwise you're going to just eventually… you just accumulate mistakes otherwise, right? And you can get away with some mistakes, but if you're just sitting there in silence or like you just are boring—because that's the real thing, right? Is like when you approach someone and you're boring, you're going to lose every time, because there's no point in talking to you. You're boring. You're making their night worse.

So in movies and shit, it's like fun because movies are basically just these nerd writers’ like wet dreams of reality. So in movies the nerd can like stumble up to the girl and go, “[Stammers] I think you're cute,” and she'll go, “Oh my God, I like you too. I've liked you all year.” But that shit don’t happen in reality. In reality, you've got to be able to talk and you've got to be able to keep the conversation fun and interesting. Otherwise, the girls are not going to want to talk to you, because they have better things to do. They're there with their friends, you know? And they weren't interested in you because they didn't approach you, you approached them.

So it's like I think guys are, like they have a little bit of like an entitlement complex in terms of like, “Well, I don’t want to entertain,” or “I don’t want to like have to do work to like talk to girls.” Well, you have to a little bit, because you have to show them that you're cool when they don't know you because you're a stranger, you know? And strangers have bad reputations.

[Angel Donovan]: Right. That makes total sense. Okay, man, like I ask this question of everyone who comes on the podcasts, so I'm going to ask you too. What would you tell a newbie to dating, you know, tell him to focus on to get as good at this as fast as possible, like your top three recommendations?

[Jon Sinn]: Number one top recommendation, join a gym before everything else.

[Jon Sinn]: Like get in better physical shape, for sure.

[Angel Donovan]: Yeah, alright. I like that.

[Jon Sinn]: That will determine more of your success than any routine, any f,,,ing… like basically take care of the basics. Let me expand to go to the gym to like take care of your basics first.

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: Like don’t have a lazy eye. We get students with ridiculous shit like, “I'm 200 pounds overweight and I want to date 10s.” Well, guess what, fatty, you're not dating 10s till you lose 200 pounds.

[Angel Donovan]: Right.

[Jon Sinn]: You know? So like get all your shit that makes you below average out of the way first. “I have a lazy eye.” Okay, go get the surgery. Like, “I have a really bad accent.” Fix your accent with two years of vocal training first, then come talk to me about pickup. “I'm balding, but I like have the horseshoe haircut because I don’t want to let my hair go.” Shave your head. All these things. Like, “I have really bad acne.” Go to the fucking doctor. That's a medical problem. A lot of dudes, like the reason they're undesirable is within their control and they're not fixing it, you know?

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: Like when I first started coaching, I had a student who had a girlfriend who he always used to say she would be a 10 if she just like got her nose fixed, but she literally had the worst nose I've ever seen in my life. Like it was like big and fat and like Roman and broken, and like it literally made her like four points less good-looking. Like she had the sickest body, like the rest of her face was okay, but that nose was just so incredibly terrible that it like cost her four points. And I always used to tell him, like if I was a girl and there was something that was costing me four points, that shit would be fixed tomorrow.

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: You know? And a lot of dudes don’t fix that. So like especially if you want to get hot girls, especially if you want to get attractive girls, especially if you want to get girls who have options, you know, like this isn't a Disneyland fucking lie where like I'm going to sit here until you, “Oh, the hottest girls are the most lonely because everyone’s too scared to approach them.” That's bullshit. The hottest girls have the most offers. The hottest girls have the most dudes hitting them up. The hottest girls have the most guys offering to buy them shit. Like that's how the world works. You can spout your hippie fucking shit somewhere else.

I live in Hollywood. Like come live where I live, and then tell me that hot girls don’t have options and that I'm not competing with literal celebrities for girls, right? I get very into it when I read shit like that on the boards. They're like, “Oh, these girls are not like screening their calls on a Tuesday night.” I'm like, “Maybe in like Iowa they're not or wherever the fuck you live, but girls in LA damn sure are screening their calls on a Tuesday night and seeing which party they want to go.”

So yeah, so you've got to kind of fix the stuff that's within your control first. So lose and/or gain weight, right? Like the other thing about cold approach, especially if you're going to bars or clubs, is there are bullies in the world, right? Like I have had a lot of students who are like 6-foot-1, like 145 pounds, who when they go out they can't approach groups with dudes in them because dudes look at them and see someone that they can beat up really easily, and they like fuck with them.

[Angel Donovan]: Right.

[Jon Sinn]: You know? That's like a real thing that happens as well, especially if you're like a really skinny, younger-looking dude who’s approaching dudes with girls. So you have to fix all of that shit first. That's how I started. I started going to the gym. That was like the first thing when I was like really young and was like, “I get no girls.”

The second thing I would say is you have to start approaching. Like don’t read a ton of stuff, you know. Check out some basic system, and then just follow that and get out and start approaching. When I started approaching, I had an opinion opener and I went to the mall and I used that opinion opener seven times a day for seven days a week to do 50 approaches a week. You don’t need to do that many, but if you're not doing at least like 20 to 30 approaches a week, you're not really progressing with this skill set. That's just kind of the bare minimum we've seen in teaching guys over the years and having a really, really high success rate with private coaching students, getting success and achieving their goals.

And the third thing I would say is you have to learn to course-correct. So if you're out there and you're doing something… Like I’ll tell you a story.

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: I have other friends who teach guys and maybe are not the best teachers, but they had a student who did 477 approaches, got four dates and one lay.

[Angel Donovan]: Wow.

[Jon Sinn]: And then they started changing up the way that he was doing his approaches, like his openers and stuff, and he was opening directly on all those. And like my first thought would be, in a hundred direct approaches, if the guy didn't get 10 phone numbers and one or two dates, I would throw direct out, because if you're not getting a 10% success rate for getting phone numbers with it, then it's not worth using, right? But a lot of these guys, they don’t kind of look at things scientifically and by the percentages and use data. Like I'm big on data. You have to track what you're doing so that you can course-correct. For me… Like I've had a lot of sticking points over the years. Like every sticking point that someone listening to this has, I've had. I had not being loud enough. I had running out of things to say as a major problem, which clearly like now I won't shut the fuck up, so that ain't a problem anymore. I had problems with attraction. I had problems with qualification. I had problems with comfort. I had major problems with last-minute resistance.

I had problems all over the board, and I think the only difference between me and a lot of guys who came into pickup at the same time as me, and even kind of became instructors but just never actually broke through to that like dream level that you like think about when you get into this stuff, as opposed to like, “Oh, I can fuck like two 6’s a month if I go out and do a lot of approaches,” which is what most instructors do, is that I was always trying to course-correct. Like I was always trying to figure out what I could fix.

[Angel Donovan]: Right.

[Jon Sinn]: You know? And any time I got something, like I wouldn't just get dogmatically attached to something. Like some guys, and this will even happen with students, like I’ll have a student who’s like, “I really like direct,” or “I really don’t like routines,” and I'm like, “Okay, that's cool, but let's see what the data says first before we start making these big proclamations because you might be a guy who needs routines and you might be a guy that direct doesn’t work for.

So it's not a one-science-fits-all process. Like that's why I've kind of brought up demographics a few times here, I've brought up this idea of like having subjects you're into, because pickup is very personalized, you know? There's no way that everyone…

[Angel Donovan]: Yeah.

[Jon Sinn]: …is going to be able to get the same girls. We're all going to be good with some girls and not good with others. You look at every guru, and if you look at the girls they’ve dated, they all kind of—besides me, and I'm not saying that because like I'm so cool, just I really don’t have a type. Like I like black girls sometimes for a couple of months, then I'm like really into like professional girls, like I'm just kind of all over. I was really into redheads for a while. Like I think besides me, every pickup guy you'll look at has a very specific type, not only because that’s what they like but also because that's what they're good with, you know?

Like not to name names and snitch, but there are a quite a few gurus who date very-new-to-the-US Asian women in the United States, which to me is a little bit like cheating. But, you know, to each his own. Maybe they just really like women who can barely speak English, I don't know.

[Angel Donovan]: Good, man. That's certainly a lot. Just on the last point, I just want to say, like course-correct is a really big deal. It's kind of a touchy subject.

[Jon Sinn]: For sure. Absolutely.

[Angel Donovan]: You have some guys that constantly jump into new topics. That's kind of their thing, right?

[Jon Sinn]: Yes.

[Angel Donovan]: I think you mentioned this earlier in the interview.

[Jon Sinn]: Yes.

[Angel Donovan]: So you have to keep a balance there. You have to course-correct but you don’t want to just keep saying, “That doesn’t work. That doesn’t work. That doesn’t work. That doesn’t work. I need something new. I need something new. I need something new. I need something new,” all the time, right? You have to kind of stick with something and make sure that it works as well.

[Jon Sinn]: Yeah, like when I'm saying course-correct, I don’t mean like you need to a hundred percent switch what you're doing, but I mean you need to try something else. And like, basically, everything comes down to kind of baselines and variations in the baseline, right? Like if everyone out there went out and approached a hundred women and just like went direct and asked girls out to dinner, you'd get a certain amount of phone numbers, a certain amount of dates, a certain amount of lays, whatever, and that would kind of be your baseline doing the most basic of approaches, sorting by looks with like very little like personality, right?

[Angel Donovan]: Yeah.

[Jon Sinn]: So for a pickup technique to be successful for you, it has to be more successful than that. And that's kind of, when I say course-correct, I don’t mean like throw everything away. I mean subtly shift things based on kind of what’s not working for you, you know? Like if you're opening really well, but then your game falls apart afterwards, you don’t need to course-correct the opener and go to a whole new guru and like change everything. You just need to try to pinpoint where it's falling apart, and then try three or four different things in that part, you know? It's not a whole method course-correction, it's tactical course-correction.

[Angel Donovan]: Mm-hmm.

[Jon Sinn]: It's doing different things rather than like throwing away a whole methodology that I really espouse, you know? Like let's say a guy can open and talk to a girl for more than 15 minutes consistently, but he just never gets attraction.

[Angel Donovan]: Right, right.

[Jon Sinn]: I would say, “Okay, there are things we can try here. Let's have you try teasing, see how that goes. Let's have you try some role-playing, see how that goes.”

[Angel Donovan]: Right.

[Jon Sinn]: “Let's have you try some storytelling, see how that goes.”

[Angel Donovan]: Yeah.

[Jon Sinn]: Right? Now we’ll see if any those fix it. Maybe they do, maybe they don’t, but now we've done something different, and now we can see if there's a variance from the original kind of baseline of “I can't get attraction.”

[Angel Donovan]: Right, right. Well, this is a good way to look at it: It's like problem-solving. So like you say…

[Jon Sinn]: Exactly, yeah.

[Angel Donovan]: …like we’re talking today about one problem, like I run out of things to say, right?

[Jon Sinn]: Yup.

[Angel Donovan]: So it's pretty easy to spot if you have that problem, for example…

[Jon Sinn]: For sure.

[Angel Donovan]: …and then you focus on finding some information that will help you with that, and then you go and practice a hell of a lot to find out what works for you, testing it, right? Rather than, as you say, jumping to new methods, which is where people really run into problems, when they start jumping around looking for completely new paradigms of how they're going to approach this thing, and then they end up going around in circles.

Well, Jon, thank you for the talk today. It's been a great session, had a lot covered there, and really looking forward to put this up. Thank you.

[Jon Sinn]: Awesome, man. Thanks for having me.