Ep. #18 How to Talk to Women and Not Run Out of Things to Say with Bobby Rio

[Angel Donovan]: Hi, this is Angel from Dating Skills Review and today the topic we’re going to talk about is conversation skills. Now, we get a lot of people asking us questions about what they should say when they first meet a girl or what they should say when they’ve kind of been talking for a while and then they don’t know what to say, or if the topics of conversation that they’re talking about are the right topics or if they’re actually kind of turning the girls off because they’re talking about the wrong things. Now, when I say popular question, it’s just like one of the big ones we get all the time. So today I have Bobby Rio from Make Small Talk Sexy. He has a course named Conversation Escalation, and Bobby has specialized in helping guys with conversation skills, so he was the person I most wanted to talk to about this subject.

Now, a bit of history on Bobby. He first got into this in 1998. So that's kind of when he got into the community through Ross Jeffries, which was pretty much the only guy who was kind of like teaching anything back then. So that's 13 years. Wow, that's a long time. In 2005, he started tsbmag.com. Some of you guys may know that it’s basically a big men’s lifestyle site with dating advice tips, articles, and other stuff related to men. So that's pretty big. And he's based in NYC. So hey, Bobby, how are you doing?

[Bobby Rio]: Good, man. Good. It’s great to talk to you again. It’s been about a year and a half since we chatted, so I’m looking forward to this.

[Angel Donovan]: Yeah, and time flies so fast. So yeah, this is great to have you on the show. Like I said, I know you’ve done all your stuff in conversation skills, so I thought you’d be the best person to talk about this stuff.

[Bobby Rio]: Cool, man. Hopefully, we can give the listeners some good tips to that.

[Angel Donovan]: Yeah. Okay, so yeah, first of all, I just want to get into the general stuff. So one of the questions we get is that guys, they’re just not really sure what to say. Are there any general pointers you would give on that first topic?

[Bobby Rio]: You know, it totally depends on where you are, in my opinion, in terms of if you’re starting a conversation with a woman at a bar for the first time or if you’re out on a date with a girl that you’ve already got to know her a little bit and now you’re out on a date, because guys kind of struggle in both situations. There are guys that email me, you know, who go out on a date and they can’t get a date to just start flowing in that fun kind of flirty way. And then, you know, same thing I guess happens when they first walk up to a woman.

So, I mean, either way, the one thing I like to tell guys, and it’s not so much what you say, it’s how you direct the conversation, which will make everything a lot easier. And the way I like to kind of explain it is imagine that there's like a giant spotlight, and when you go up to talk to a girl your goal is to get the spotlight shining on the two of you as quickly as possible.

Now, what happens is a lot of guys do the opposite. They either go in and they put the spotlight on her by just drilling her with questions, which makes her uncomfortable and it creates sort of an awkward vibe, or they try to do all the talking about, you know, they’re either telling stories or they’re even using one of those, you know, something from like routines or something like that where they’re talking about something else, and now they’re putting the spotlight on them, which kind of is a lot pressure.

And I think that's why a lot of guys quickly run out of things to say, is because it’s almost like if you ever talk in front of a camera, and it’s like you can be totally natural and fun with your friends, but the minute one of your friends like puts a video camera on you, you just kind of freeze up and you just don’t know what to say. I mean, I’ve seen it happen. I used to be a videographer at weddings, and people that really were the most talkative people in the world, when you find a camera on them, they couldn’t talk.

So with girls, I like to say try to get it where the spotlight’s not on her, it’s not solely on you, it’s on the both of you, because it makes the conversation flow a lot easier. And how you do that is you get to discussing the interaction rather than asking her, you know, you tease her about something. You kind of rile her up a little bit about something that she’s opinionated about but she’s directing it towards you. It’s not about the subject in itself.

And the reason I try to stress that is because a lot of guys say, “Well, Bobby, what should I talk about? What’s a good topic?” And the problem is a lot of good topics that make conversation really easy—travel is a topic that makes conversation really easy. I mean, you want a woman that if you start talking about traveling can share travel stories for two hours and the conversation will never ever end. But the problem is that you put the spotlight on travel the whole time and you didn’t develop any sort of connection with her, and then once that subject of travel dies down and now you’re both standing there and there’s no chemistry, there's no spark…

So that's the first sort of thing I want to keep in mind, is that it’s really hard for me to say what to talk about because if I tell you, okay, talk about music or talk about childhood memories, which are great topics, they’re emotional topics, but if you tell somebody to talk about them but they don’t realize how to talk about them, they run the risk of just spending an hour talking about a topic and then the topic kind of dries up and she has no motivation to keep talking to you now that that sort of mutual interest you guys had in common is not there anymore. Does that make sense?

[Angel Donovan]: Okay, just to kind of reiterate, like what I’m getting from you is that you’re saying like, okay, there are good topics like travel, for instance, which are easy topics to start with and everyone can talk of them, but you really have to talk about these subjects in a certain way in order to get both of you involved rather than just to run through the topic and kind of dry it out. Is that where you’re coming from?

[Bobby Rio]: Exactly. So, for instance, like let's stay with the travel thing. So if travel came up as a topic, a lot of guys will make the mistake—and I’m guilty of this. Everything that I’m going to be talking about I learned the hard way. I started off as the absolute shiest, worst conversationalist in the world, so I’m not criticizing anybody. This is all from personal experience, where I know myself or guys, they start talking about travel and they immediately want to talk about their vacation.

So let's say she tells that she just got back from Mexico and you were there last year, you had a really good time, and now all of a sudden you want to just tell her about your time in Mexico. And on one hand it fills up the air, yes, but on the other hand it’s not really doing anything to bring the two of you closer to generate attraction.

[Angel Donovan]: Mm-hmm.

[Bobby Rio]: Whereas if you made a comment to her like, “You know, I can’t see you going to Mexico. You seem like the kind of girl who couldn’t deal with like third world kind of things. You seem like you would need like a fancy hotel.” You start telling her things about herself in relation to travel, of the topic, but you’re getting the focus in on how you see her, because now when she talks back to you, she’s now talking to you rather than talking solely about traveling.

Now she may defend herself and say, “No, I love it. I’ve been to Africa and I had a great time. Why do you think that about me?” And now you say, “Oh, it’s just the impression I got from you, like you have your perfect manicured nails. I just couldn’t imagine you in Africa having to take a shower in a hut,” or just kind of talking about a subject but continually bringing it back to her or to you.

[Angel Donovan]: So would you say this is like basically putting a little bit of tension in between you in the interaction between you so that she’s got to say something back to you but it’s now about the both of you, like you were saying earlier, right, the spotlight on the both of you instead of just being the topic because you put a bit of pressure on her?

[Bobby Rio]: Oh yeah.

[Angel Donovan]: Then she has to respond back towards you rather than just talk about the topic.

[Bobby Rio]: Yeah. Exactly. You want to try… My personal favorite way to do it is through teasing a girl and kind of—but there are different ways and everybody has their own style.

[Angel Donovan]: Yeah.

[Bobby Rio]: I just happen to feel most comfortable… I like girls that know how to banter, so I like to kind of get into that teasing banter vibe as quickly as possible. It’s what I have fun doing.

[Angel Donovan]: Mm-hmm.

[Bobby Rio]: But you know, in general, it’s any way you can get that spotlight shining on the two of your interactions along with whatever you’re talking about. So if you’re telling her a story about your childhood, you also want to mix in her and getting her to ask you about things or get her to sort of laugh at you. And it could be in like a funny way about how when you were a kid… You want her directing the questions about how she sees you and, “Oh, I couldn’t imagine you doing that when you were a little kid.” It’s always got to be a mixture of the experience you’re having now together along with whatever else you’re talking about.

And I think that mistake is guys get caught up in rapport, and when you’re in a really strong rapport with a girl and you are talking about something like, let's say, a band… Let's say you start talking about a band you both like. You both happen to like the Dave Matthews Band and she starts telling you about the concert she went to and now you’re both talking about your favorite songs and stuff, it’s very hard then to like kind of break away and get into that flirtatious mode. And what happens is a lot of guys don’t know how to and they wind up talking for an hour and a half thinking that, “Hey, this is going really, really, good,” but it didn’t. She just enjoyed talking about her favorite band with you the same way she would like to kind of post on a forum somewhere with an anonymous person. That's about the extent of the attraction she feels towards you.

[Angel Donovan]: Great. So are you saying there's a kind of time limit on this? Like say if the guy starts talking like… Okay, let's take another scenario, right? He's at some kind of business conference and he meets a girl he likes and they start talking about something. Has he got a time limit to start introducing this kind of more flirtatious personal conversation between them or what would you do in that situation?

[Bobby Rio]: I say as quickly as possible, and the reason I say it is… I say you have to establish yourself as a flirt as quickly as possible because there's sort of something that I like to refer to as a theory of expectations, and the sooner she says, “Oh, that's how this guy is,” the minute she’s like, “Oh, he's a flirtatious guy,” you can get away with a whole lot more throughout the rest of the conversation than if her first impression of you is, “Oh, he's a serious guy.” If now 20 minutes in you want to kind of flip the switch, it kind of throws her off a little bit and it makes it a lot more difficult. So the quicker you can get into a flirtatious mode, the better.

So even if you’re at a business conference, generally what I would do is quickly make like a banter line real quick. Let's say she had her nametag on and I would just make a funny joke about her name or make that oddball guess about what her occupation was, just something where right away she says, “Oh, this is like flirty kind of guy. This is a jokester. He's not too serious of a guy.”

And then I would move in and have that normal conversation for a bit, you know, because at a business conference you can do that, but you’ve already established you’re flirty, so now you can start throwing in some more bait, you know, cast your line in there when you see an opportunity and get it back out towards the two of you if that's your goal and your goal isn’t just to connect work-, business-wise.

[Angel Donovan]: Great. I take a few things from that. So, I mean, first of all, if you don’t kind of open this window to this more personal type of conversation and flirty type of conversation early on, then you could get in trouble later when you do try to introduce it because she’s not kind of seen you that way and she might take it badly. And some guys who have kind of had these negative reactions that they’ve seen, like sometimes I think it is where basically they’ve been a normal guy, and then they haven’t said anything crazy or anything but they tried to introduce this more personal flirtatious kind of thing. And maybe they’ve been working with the girl for a year in the office and then one day they learn a line and they take it out and they run it, and she reacts really negatively to it. And what I like about your point is like, yeah, that line would have been great if it was in the first 10 minutes when you first met her, but a year after she sees you as already a serious guy, she’s going to take it in a very different way.

[Bobby Rio]: Yeah. That's exactly true. And there's actually something real quickly a little bit more powerful about it, and it has to do with yourself. And what I mean by this is the way somebody expects you to act, it turns out to make you act that way. You know, I learned this the hard way because, like I said, I was a very shy introverted person. And what I found was that if I started off shy around somebody, I found myself always sort of reenacting the way that I was, the way that they see me. If I know somebody sees me as a shy person, even years later, like I had this difficulty when I went back to meet some people I knew from high school who I knew they saw me as a shy person, so it was very hard for me to kind of go back to that fun, sort of more outgoing person.

And that's why it’s really important also is that, just for yourself, when you establish yourself as being fun and a flirting kind of guy, it actually makes it easier for you because the other person’s almost like waiting for you to say something funny. And if you’ve ever been with like a friend who thinks you’re really funny and they like almost laugh before you sort of say it, it just makes it so much easier to think of things to say and to be funny when the person’s expecting it as opposed to when the person thinks you’re serious or when the person thinks you’re shy or timid or whatnot.

[Angel Donovan]: Yeah. No, man, totally, very, very, very good point. So like I guess we’re getting into a little bit how to become more conversational and what would be an easier way to do it, right? So if we establish a few rules of like this is how you get better conversation skills, this is what you should be doing, so how would you go about learning them in the easiest way possible?

[Bobby Rio]: The first thing I would do, and I recommend it to guys and I find this extremely interesting, and I think that the influx of dating advice on the Internet has good things and has bad things, and one of the sort of bad things that I think is is that I think a lot of guys are really intimidated. I know personally—like I do mentorship. I have a program called the Social Training Lab where guys can email me and deal personally with me.

[Angel Donovan]: Yeah.

[Bobby Rio]: And it amazes me that these guys are very new to it. But you know, they’re on the Internet surfing different sites and they come across different pieces of advice, and some of the advice they’ll come across is like, “You should be doing five day game approaches every single day,” or “You should hit on 10 girls at a nightclub every time you go out.” And the thing with that kind of advice is that in theory it sounds good, but in reality, I mean day game approaching, approaching a random girl on the street or a random girl in the mall is like the hardest possible thing you can do. I mean, even guys I know, like naturals that for their entire life these guys have been getting laid like rock stars, they don’t approach girls on the street.

Now, I’m not saying that there are amazing pickup artists out there that can’t do it, but I’m saying it’s not a general thing to do. It’s not something that like the best guy that you went to school with in high school who got all the cheerleaders, he doesn’t walk down the street and do day game approaches. It’s hard.

[Angel Donovan]: Right.

[Bobby Rio]: I think that when you’re practicing in that kind of environment in a guy who is just with no conversation skills, he's putting like the absolute most kind of pressures. It would be like learning to ski on a black diamond. When you want to learn to ski, you go to the bunny slopes. You make it as easy on yourself as possible.

[Angel Donovan]: Yup.

[Bobby Rio]: So, for me, I mean, the location of where you’re practicing—and it’s interesting because earlier you brought up business networking meeting, I personally… If somebody is over 25 years old, or even in their mid-20s and over, I tell them find your local young professional networking meetings because they’re an amazing place to practice, because here you’re going to a place where the girls that are there, they want to talk to you. They’re there to network and to socialize.

[Angel Donovan]: Yeah.

[Bobby Rio]: Now, they’re not necessarily there to meet guys, but to practice your skills on them, I mean these girls, they’re going to talk to you. They’re not going to blow you off. They’re not going to look at you like, “Why the hell are you stopping me when I’m walking down the street? I’m late for work.” So that's the first thing. It’s find easy places to practice.

Other easy places, you know, when I learned most of my stuff is back after college I got a part-time job waiting tables at a restaurant with a whole bunch of girls my age. Angel?

[Angel Donovan]: Yup, I’m here, man. I’m following everything you say. It’s all great stuff.

[Bobby Rio]: Oh, I’m sorry. My phone clicked off and I thought that you hung up. Sorry, I’ll just…

[Angel Donovan]: No problem. Hey, tell you what, let's just leave a little gap here so I can identify where this is and I’ll edit it.

[Bobby Rio]: Okay. So yeah, back in college, right, when college ended and I was into the real world, and without having the sort of comfort of my college social circle, I started to lose a little bit of steam and kind of got intimidated to be back out there in the real world sort of dating, and I wanted to practice. And to me, I got a job as a waiter in a restaurant where I worked with about 15 girls who were anywhere from 18 to 30 years old, and the entire day was me just practicing my conversation skills on these girls, whether it was while we were working or when work ended we’d sit around and we’d have a beer together. And that's an easy place to practice. There's no pressure on you. The girls are going to talk to you, and now you can get good at it. You can kind of test things out and see the reaction.

I mean, if a guy goes out and he's like, “You know what? I want to practice my conversation skills,” and he goes to some loud nightclub and he hits on this perfect 10 who’s just been sick of getting hit on all night, she’s not the perfect person to practice on. Like I said, he’s like saying, “I want to learn to ski,” and going, “I’m going to ski down that black diamond today.” You’re going to fall and you’re going to think, “I’m never going to learn this.” So that's definitely my first piece of advice, is practice on girls that are going to be receptive to talking to you.

[Angel Donovan]: Right, and in social situations basically that you’re kind of used to and that you’d expect to be talking in, right? So you gave the example of a restaurant there. Like a personal example I have was I worked in bars and you know, obviously you have to talk with the clients, right?

[Bobby Rio]: Exactly.

[Angel Donovan]: So, you know, I can say that was very easy for me in the day. And then I was learning salsa for a while in my early days learning about dating advice, and the girls naturally want to talk to you then too. So that can be another easy place, as you say. So to pick up on what you said earlier, you said it was like kind of hard to go into an environment where there's an expectation on you that's already set for you to be shy, for example? So what I take from that is that you should kind of aim for a new environment, like aim for an easy environment to talk in where you’re expected to socialize but which is new and different from where you currently kind of operate socially.

[Bobby Rio]: Yeah, and you know what, it’s funny that you mentioned salsa because, like I said, I have a bunch of clients that I personally coach, and just recently the second guy, second guy, and it was only one—I won’t even bring it up, but the second guy who lost his virginity to a girl he met in a salsa class, this 28-year-old, 29-year-old guy, that it’s just a really great place like you said. The girls are friendly. I did salsa but I didn’t like…

[Angel Donovan]: The girls that go there are looking to meet guys, so…

[Bobby Rio]: Yeah, they’re there just to increase their social life. I mean, a lot of people don’t realize and they think, “Oh, a pretty girl has a lot of friends.” But you know what, when you get into like your mid-20s, a lot of these girls get out of college, their friends start getting married, and now you have a lot of really attractive good girls who they don’t want to go out to bars anymore because they’re just kind of tired of it, but they want to meet people. So when you find these kind of sort of secret spots where these girls are hanging out, it just makes the whole game a lot easier for you, especially if you’re not the kind of…

You know, if you’re the kind of person who loves going out to bars and nightclubs, then go for it. But if you’re not the kind of guy that likes that scene, don’t force yourself. Don’t think that because that's what guys in some program you were listening to, they’re talking about bars and clubs, but that doesn’t have to be where you go out and practice. There are a lot of better, easier locations.

[Angel Donovan]: Yeah, exactly. Don’t make it hard on yourself if that's something that you’re not going to find easy. Here’s a situation, right? So if they go on a date, and one of the questions that we often get is, you know, you’re on a date and it seems like a long time to be talking, okay? So most guys, they’ll run out after an hour or so of talking, they kind of run out of subjects, and in particular they have an issue where if the girl stops kind of talking and contributing herself, right? So they’ve been talking for a while but things kind of dry up from the girl’s side, have you got any suggestions there on how to kick the conversation back into alive mode?

[Bobby Rio]: You know what, two things. I’m going to give you a tip and a second. First, I think one of the reasons guys run into that problem is because they spend—you know, I just got an email from a guy who told me he talked to a girl on the phone for an hour and a half before he met her on the date, and this was his first date with her.

[Angel Donovan]: Right.

[Bobby Rio]: They met on an online dating site. And if you talk to a girl for an hour and a half on the phone and then you go out on a date and you spend two, three hours with her, it’s going to get tough to keep it going. So, A, you want to cut down on the phone time with a girl before a date, and then when you’re on a date with a girl, you want to be escalating, because it’s kind of like driving a car in a sense. You have to shift gears, and if you’re in the same gear for so long, it’s going to get boring. There's no magic kind of thing. If you’re sitting there and you’re having the same sort of level of conversation for two-and-a-half hours, no matter what you’re talking about it’s going to start getting boring.

So you want to shift it. You want to slowly… Like you want to start off in like first gear, which is sort of like a little vaguely flirtatious and fun, but at the same time, if this is an early date, it’s still a little bit of the normal get-to-know-you kind of conversation. And then at some point if you’re having a good time and you sense that there's flirting, you want to downshift a little bit, and at that point you begin to express a little bit of sexual aim to her and kind of feel her out on that level, because now you’re sort of opening up a whole other can of worms of things to talk about.

I like to test a girl out in that sense and see how open she is to kind of taking it to like a more R-rated level. So what I’ll do is if I’m out, you know, let's say I’m sitting at dinner, and dinner’s probably like the worst thing you can do as a first date with a girl, but let's just say you went out to dinner with a girl and you start running out of things to say, and let's say there was like a table, like a few tables up and there's like a swanky-looking kind of couple there, you can just make a comment about them, say, “You know, those two over there totally seem like the swanky seventies swinger type.”

And you know, she’ll look at them and she’ll probably laugh and you say, “Do you see it or is it just me?” And then she gives you her opinion, and then you can say, “You know, when I look at you, I kind of get that vibe from you too.” And you just kind of say it joking around and you just see where she takes it. She may go, “What are you talking…? I would never do that,” and then you know, “Oh, I have to go back into the other gear.”

But she may laugh, you know, she may open up a whole new realm of conversation. She may tell you about one of her friends that is a swinger. You may change the subject from swinging and you can something like, “Yeah, it’s always the ones you least expect it, like you look like an innocent girl but it’s always the ones that least expect it that have the kinkiest side. Like so come on, tell me, do you have anything? What don’t I know about you? What is your sort of secret side that I don’t know yet?” And you kind of fish. It’s just a game of fishing. You’re throwing stuff out there and you’re waiting to see where she kind of takes it, what she bites on and whatnot.

So as long as you’re always sort of changing the gears, you’re going to be alright. So if you start off in first gear, that's flirty. Then you downshift to, let's say, where you start talking about things that are a little bit more R-rated, and that I consider things like talking about secret sides and swingers and stuff like that. You’re not talking X-rated at this point. You’re not bringing up sex itself. You’re not talking about fucking or anything like that. You’re just talking about things that have sexual connotations.

[Angel Donovan]: Mm-hmm.

[Bobby Rio]: If she’s still biting and you’re having a good time with her, then you have to downshift again and you have to let her know you find her sexually attractive, and you make a comment to let her know like, “Oh, that thing you just did just drove me crazy,” or “The perfume you’re wearing is really turning me on.” You say something to her that lets her know you find her sexually attractive, because now you’re taking it to another realm. Now she knows, “Okay, this guy finds me sexually attractive.”

And a lot of guys think, “Well, the girl knows that.” The girl doesn’t really know that. An attractive girl might know that a guy likes them or wants to be their boyfriend or whatnot, but not all girls know if they’re sexually attractive to men. So when you let a girl know that, it kind of opens up another sort of spot in their brain where like it excites them in a new way and it kind of recharges the conversation.

And then from there you want to kind of sort of escalate the flirtation, get it a little bit more sexual. You can talk about going back to her place and having a pillow fight, or if she says something you can joke that you’re going to spank her later. You just have to keep on shifting. You don’t want to stay in a plateau because when you stay in a plateau it’s going to get boring. It’s impossible to have three hours of conversation if you’re not continually changing gears.

Now, that doesn’t mean… If she reacts to something in an unfavorable way, you sort of back up a little bit, but you’re always playing the game of, ”Where can I take this?”

[Angel Donovan]: Right, right.

[Bobby Rio]: Yeah.

[Angel Donovan]: And I guess what you’re saying here is, first of all, like I see what happens with guys is they get a bit nervous and then they tighten up. Their reaction is to restrict with they’re talking about and to get more concerned about exactly what they’re saying. Whereas you’re advising basically the exact opposite, right? You’re saying kind of relax, experiment with different types of conversation, pushing the boundaries here and there. And like a thing you point to is like it’s not a big deal if you kind of like step out into one direction and she’s not biting, because you can step back and then try and go another direction, and she’ll get back engaged when you’ve gone in a direction which she’s comfortable with.

[Bobby Rio]: Yeah. And the worst thing guys could do is try to predict what a girl’s going to be comfortable with, because I can tell you from experience, you never know. I mean, my current girlfriend, she’s on the conservative side when you look at her. She’s a Colombian girl, very raised sort of Catholic.

[Angel Donovan]: Yup.

[Bobby Rio]: And you know, she’s all around good girls. She doesn’t even curse, never tried drugs. And if you knew that about her going in, you’d probably restrict how you were to her.

[Angel Donovan]: Yeah.

[Bobby Rio]: But at the same time, on the first night we went out, we got to talk, we were talking and we had a mutual friend who had a sister and I was like—this was later on after we had been in New York together, in a couple of different locations, and now we had gone to a bar to kind of have a late-night drink.

[Angel Donovan]: Yeah.

[Bobby Rio]: And we’re talking about our mutual friend’s sister and I said, “Yeah, you know, one time I walked in on her kissing another girl,” and she said, “Oh…” We got into talking about the idea of girls kissing, and then she’s like, “Well, have you ever had a threesome?” And I started telling her a story about how I was at a wedding and the girl that I was with offered it to me but it got broken up, and she says, “Well, would you have done it?”

And so that question right there, “Would you have done it?” right? It kind of separates how a lot of guys think. A lot of guys—and I used to be this way, too—would have said, “No, I wouldn’t,” because they think that that's going to make them sound more gentlemanly or the girl’s going to find that noble. And I just looked at her and I go, “Fuck, yeah, I would’ve. You don’t turn down an opportunity…”

And she still to this day, you know, she said, “That's the moment I knew I liked you because every other guy I went out with on the first date, he would never have thought about saying that he had a threesome or that he was disappointed. He would have sat there telling me how he wouldn’t have done it.”

[Angel Donovan]: Yeah. Boring. [Laughs]

[Bobby Rio]: Yeah. And it’s true, you think you’re playing it safe but you’re playing it boring.

[Angel Donovan]: Yeah.

[Bobby Rio]: When you’re just honest with girls, it’s so refreshing for them. It’s like a breath of fresh air when they get a guy who is not trying to censor himself and trying to play that he's like the perfect gentleman.

[Angel Donovan]: Yeah, yeah. Exactly. And you’ve got to see that no matter where the girls come from or what their background is, you know, you gave the example of a Colombian with a Catholic background and stuff, they will be watching the same TV, right?

[Bobby Rio]: Yeah.

[Angel Donovan]: And the media these days is pretty sexualized, so it’s impossible to avoid all of these topics, and I think it would be difficult for a girl these days to not feel comfortable with talking about them because she’s seen it for the last 10 years on TV, right?

[Bobby Rio]: Yeah. Yeah, definitely. And so back in college, just if anybody’s like doubting that girls really think this way, back in college I dated a girl who was in a sorority. And she lived in a sorority house with about 15 girls, and I used to stay there quite often. I’d just sleep over. It got to the point where like they didn’t even know I was around. I was with my girl and they would just talk openly like I wasn’t even there.

[Angel Donovan]: Yeah.

[Bobby Rio]: And that experience probably was one of the best things that ever happened to me because I got to see just how raunchy and stuff girls actually are, like it was probably worse than being in a frat house listening to these girls talk about what guys they wanted to fuck, how much a guy was a pussy for not making a move. It was just nonstop.

[Angel Donovan]: Yeah.

[Bobby Rio]: So I just don’t like to imagine that, and if you saw any of these girls on campus, you’d look at them and you’d think, “Oh, she’s a cute little cheerleader,” but back in the sorority house when nobody was watching, the stuff she’s talking about is just amazing. And you have to keep that in mind because it really expands… When you don’t have that self-censorship of what can I not say, what’s going to offend her, it makes it a lot easier, this whole kind of question that we started with at the very beginning of what to talk about.

And it’s when you stop sort of limiting what’s okay to talk about and you just take some chances and see where it goes, that's where it starts to flow and you get in the zone and it’s just a spontaneous, natural conversation rather than if I had said to you, “Well, you should talk about these four topics. Because then, you know, if a guy’s trying to force those four topics, it’s going to sound forced and it probably won’t go anywhere anyway.

[Angel Donovan]: Yup, yup. Exactly. Alright, so while we’re on the subject, guys will often ask, are there any conversation topics you should avoid, a danger zone or anything like that?

[Bobby Rio]: You know, it depends. It depends on you. And I know that's probably an answer guys aren’t going to like, but if you’re the kind of guy who winds up in the friend zone a lot, it’s probably not a good idea for you to get a girl talking about her ex-boyfriend because if you don’t know how to handle that, you could wind up turning into her therapist and it could kind of kill the momentum or the attraction of the conversation.

[Angel Donovan]: Yeah. Mm-hmm.

[Bobby Rio]: If you are a little bit more skilled, it doesn’t really matter what you talk about. People say don’t talk about politics. You do run a risk with stuff like that, religion or politics, only because… You know, normally I love to be on the opposite side of argument with a girl, like I’d 10 times rather a girl say something and me have an opposing view because that's where the tension and the flirtation is, but politics and religion, if a girl’s really like worked up about it, it could just turn into like a preaching sort of conversation that it’s just not going to lead to anywhere. So those two topics.

Other than that, I mean, there's really not anything that pops in my mind of like, “Don’t talk about it.” People say interview mode like asking lots of questions and stuff, but if you know how to talk about anything, there's really no topic that is that bad.

[Angel Donovan]: Yup, totally agree, man. Alright, so that's the bad side of it. So you’ve been talking a lot about kind of sexual topics. Are these topics you should be moving towards? Like are there any kind of like targets that guys could have in their line of sight like, “Oh, I should introduce that topic at some time. These are the kinds of things I want to talk about while I’m with her.”

[Bobby Rio]: Well, observations about her is a good one.

[Angel Donovan]: Yeah.

[Bobby Rio]: You know, at some point you’ve got to be making observations about her. Not in a row. You don’t want her to sit there and bombard her with five of them in a row, but sprinkling in observations about her throughout the conversation is killer. Those are sort of… They get the spotlight going, that I talked about earlier. They get her looking at you, thinking about you, and the spotlight’s on the two of you and how you’re sort of seeing each other. So that's a good topic.

You know, childhood memories I love personally. It’s just a fun topic. What I like about it is that, especially if you’re at like a bar and the girl’s sort of looking at you like, “Oh, he's just another guy hitting on me,” then you start to kind of bring it up like, you know, you talk about some TV show you both liked when you were like 6 years old. It kind of makes her think, “Oh, this guy, there's more to him. He's three-dimensional. He's not just some drunk guy at a bar. We actually have a shared sort of history together.”

So I do like that. I mean, as far as sexual things, if that was what you’re asking, I like to use stories, and that's what I kind of talked about earlier, how, with your job, let's say, I can turn my job into a sexual story. And I’m not talking about my job recently running PSB Magazine and dating advice. I used to be a painter for a while.

[Angel Donovan]: You’ve done some interesting stuff, man. [Laughs] You’ve done some interesting work.

[Bobby Rio]: Yeah, I don’t mean painter. No, I don’t mean painter like painter painting pictures. I mean, like a house painter.

[Angel Donovan]: Oh, okay. Well, it’s still interesting, right? You’ve got variety in there.

[Bobby Rio]: Yeah. But you know, and for all general purposes, if you’re at a bar you’d think, if a girl asks you what you do for a living, house painter is probably not a job that's going to get her sort of attracted. It’s not like sort of a high-status job. It’s not a sexual job.

[Angel Donovan]: Yup.

[Bobby Rio]: But I learned through the use of stories that I can quickly get into a sexual realm by simply—and I’ll use examples. The girl said, “Do you like your job?” “Yeah, you know, it’s alright. The more interesting thing though is like what you find in people’s closets.” I’m like, “When you’re painting a house, you’d think people would hide stuff. And it’s always the innocent, old lady that you open up a closet and you find like a big box of sex toys or something.” I’m like, “It’s always the ones you don’t expect.” And like right there you just went from talking about painting houses to kind of bringing up finding a box of sex toys in an old lady’s…

So it’s kind of funny enough where it’s not like, “Oh, this guy’s a pervert talking about it.” You’re like kind of telling her a story, but at the same time you just introduced sex stories into the conversation and now you can see where she’s going to take it. Is she going to back off and say, “Oh my God, that's horrible?” Or is she going to laugh and say something like, “Well, you know, every girl has them,” like you don’t know and it’s your job to find out, it’s your job to throw this stuff out there and see where it goes.

[Angel Donovan]: Yeah. Yeah. Sure. Sure. Hey, so you made me think of something. In terms of like, you know, we’ve had ex-girlfriends and stuff and we’ve had experiences with them, and we’ll be out with a girl and we’ll be doing something, and often, for some reason, whatever you’re doing, one of these past experiences will pop into your head. Is that the kind of thing you want to talk about? Because I think a lot of guys, what they do is they kind of avoid talking about ex-girlfriends and their experiences and stuff.

[Bobby Rio]: Yeah, I don’t mind talking about them. I don’t dwell on any particular girl, but if I have a story, like earlier, that I went to a wedding with a girl that I had dated and her friend got drunk and wanted to kind of talk me into having a threesome and you know…

[Angel Donovan]: Yup.

[Bobby Rio]: It was actually a funny story. A story like that, if the situation came up, I would have no problem telling. I wouldn’t get into like a story like, “Me and my ex-girlfriend, we went on this vacation, it was so good and romantic.” If it’s a story that's like kind of romanticizing one of your past relationships, it’s really… No.

[Angel Donovan]: Okay, yeah, especially when it's a danger area, if you feel like you’re still into one of your ex-girlfriends and you start to talk about her, maybe that's something you should stop talking about pretty quickly because you’re more likely than not giving some kind of emotional vibe off about that that's going to give bad signals.

[Bobby Rio]: Exactly, so yeah. If you’re telling a story and you're romanticizing it, it’s not… But if you’re just telling the story because it’s funny and it contributes to like the topic at hand, then go for it.

[Angel Donovan]: Exactly. Exactly. Alright, man, you’ve kind of brought up, you’ve danced around the issue of humor a lot, right, for teasing and banter. Like some guys might not have a good feel for what teasing and banter is and humor. Are there ways to learn about this? This is kind of like a conversation style, so what would you advice guys who are thinking, “Okay, so I’ve got to be a bit more funny and make fun of her?” How should they learn about that?

[Bobby Rio]: I’d say—and this also comes from experience because I learned this the hard way—there's a very fine between teasing a girl and being an asshole, and the way that it is is when you’re commenting on something that she can’t change or something that's very personal to her or her looks, you really run the risk of being an asshole. So no matter how funny you think a joke about her nose is or her weight, or even the way she has her hair that night because a lot of girls put a lot of effort into it, and for you to say that, I know some pickup artists would recommend that kind of stuff, but you run the risk of coming off like an asshole.

[Angel Donovan]: Yeah.

[Bobby Rio]: Making fun of a tattoo she has.

[Angel Donovan]: That's bad. I’ve done that accidentally once before. [Laughs]

[Bobby Rio]: Yeah. [Laughs] Me too, man.

[Angel Donovan]: That doesn’t come off, unfortunately. [Laughs]

[Bobby Rio]: Yeah. But the best thing to find humor and when you’re practicing is her, is the way she’s acting. So if she says something and it comes across as bossy, you can make fun of her bossy side. A lot of times I’ll be telling a girl a story and I’ll throw in like a totally made up like exaggerated lie, and then when she believes me I’ll make fun of her, I’ll tease her about being gullible, and I’ll start talking about how… You know, I’ll use that sort of as a piece that I can use throughout the rest of the conversation. I’ll continually tease her that, oh, she’s naïve, she’s gullible. Because things like that, you make it like, “Oh, it’s so cute, you’re so naïve,” or “You’ve got a bossy side.” Or even if she’s being a little bitchy, you can make fun of her for being cranky.

[Angel Donovan]: Right, right. Man, I just want to say something there, because like, I mean, the way I kind of look at it, you’re talking about behaviors, right, rather than aspects of themselves, is like things they do. So it’s nothing permanent, and I don’t think I’ve ever come across a girl who got really offended about that.

[Bobby Rio]: Exactly, yeah. Yeah. You want to—exactly—tease her about her behavior rather than her looks or any that's like… You don’t even want to tease her about her job because, you know…

[Angel Donovan]: Yeah.

[Bobby Rio]: Like I’ve done this. Like I met a girl out at a bar, they were an accountant, and I started like making fun of them like being boring because, “Oh, you’re an accountant. You must be really boring.” But, you know what? Like they went to school, they wanted to be an accountant, and here I am sort of belittling what they do for a living, and they may really like it.

[Angel Donovan]: Yeah. Or worse, man, she might actually be bored and she might be insecure about where she’s going in life.

[Bobby Rio]: Yeah, yeah.

[Angel Donovan]: And you know, you’re not going to make her happier by bringing up the whole topic.

[Bobby Rio]: Yeah, exactly. So yeah, so I think you hit it on the head with target behaviors as your source of humor. And practice, you know. Practice spotting things, like try to find things that you can twist.

[Angel Donovan]: Mm-hmm.

[Bobby Rio]: Look for a girl to say something that sounds a little bossy or sounds a little like cranky or just try to find things she’s saying that you can twist and exaggerate them to be a little more of the behavior you want to make fun of than it actually was. So she doesn’t have to be completely bossy, but if she’s getting a drink and she takes the drink too fast from the bartender and doesn’t say thank you, you know, you can kind of use that behavior to tease her a little bit. Just things that she does. When you have your eyes open and you practice, it starts to become a lot more natural to you.

[Angel Donovan]: Yeah, yeah. And I’ll say, like I think one of the keys to this conversation stuff, now you’re talking about it, it’s like observation skills, right?

[Bobby Rio]: Yeah.

[Angel Donovan]: Because that's what develops the interaction, and I don’t know if it’s been the same for you, but over the years as I guess I was becoming more observant, I started getting the girl saying, “Wow, no one’s ever noticed that about me before,” right?

[Bobby Rio]: Yeah.

[Angel Donovan]: And today this happens all the time, right? But observation is a skill, and it’s part of the conversation, really, right?

[Bobby Rio]: Yeah. Yeah, because, you know… And like you’re saying, it’s not only what you’re observing about her, which like you said, when a girl notices that you’re observing, it’s attractive to her because she feels like, “Oh, this guy gets it. He sees what’s going on, he knows it,” but it’s also good because you get to observe… When you get a little bit more aware of what’s going on within a conversation, like I talked about earlier, when you’re able to say, “She just kind of gave me a weird reaction there. Let me steer it this way and let's go in a different direction with this…”

[Angel Donovan]: Yeah. Yeah.

[Bobby Rio]: You know, you’re able to just kind of tune in to reactions you’re getting and sort of the subtle things she’s saying. It allows you to take it in different directions.

[Angel Donovan]: Yeah. Yeah. Observation is key. But it’s not something that comes, I mean, didn’t come naturally for me at all. I think it’s something that was learned over time from kind of paying attention to watching and listening. I don’t know how it turned out for you.

[Bobby Rio]: Yeah, very similar. I’ve always been a sort of a shy person growing up. I was always like an observer but I never knew how to vocalize my observations.

[Angel Donovan]: Mm-hmm.

[Bobby Rio]: Like I would sit and observe things about people and think of things to say, but I didn’t know how to kind of bring it into a conversation without it sounding weird. And going back to the whole idea of when somebody sees you as a shy person and out of nowhere you like make an observation about them, like, “Oh, you’re pretty bossy,” it’s not going to go over well because they feel like, “Why is the shy, weird guy telling me I’m bossy?” But if you establish yourself as a fun guy right off the bat, and then you make a little joke about her being bossy, it’s a lot easier. But yeah, that same thing, as you said, you know, it took practice of how to implement it and how to get it to sound natural and not really like…

You know, I think that's probably the hardest thing learning this, is when you’re studying material, is to not feel like you have to use the exact material. So I gave a handful of examples through this interview where I talked about, let's say, my story of when I used to paint houses and I found a box of sex toys and it kind of would lead to a sexual conversation. I know, myself personally, when I used to listen to these years back and I heard people talking about what they said, I would go out and try to use that same story or try to force a story like that into my conversation and it just wouldn’t come out naturally. It would feel forced and it wouldn’t have the same effect. Whereas when you sort of learn how to, I don’t know if calibrate’s the right word, but you just learn to observe when…

Everybody has their own stories, first of all. I mean, that's a whole other topic, is finding the interesting things in your own life and finding ways to take aspects of your own life and twist them into something a little bit more interesting. Right there, that you should be doing. But it’s really not about copying word for word what works for somebody else. It’s about taking the principle of why it works and then introducing that into your conversations.

[Angel Donovan]: Yeah. Yeah. And so this can take a little while. It can take a long time depending on how much effort you put into it. Alright, before we move on to the next topic, I just want to hear one thing. Like say I’m desperate and I really am having a hard time kind of learning just to converse with women and feel comfortable with it and stop the dreaded silences that come up all the time, like I’m ready to do anything, what should I do? Like some of the ideas I’ve got in my head is like, okay, go and get a job in sales or force yourself into social situations so you can break out of it. What would you suggest?

[Bobby Rio]: I’m sorry, so are you asking for a technique to get out of awkward silence…

[Angel Donovan]: Yeah, not a technique, like an approach to get myself out of this, to start learning about this stuff and become more conversational and social if I’m having a hard time kind of getting skills…

[Bobby Rio]: Oh, pushing yourself to do it?

[Angel Donovan]: Yeah, yeah, kind of pushing yourself to do it and become more conversational and just get this fixed.

[Bobby Rio]: Okay. The thing I would recommend to somebody who’s dealing with that is to set a condition in place that makes it inevitable that it happens in a sense.

[Angel Donovan]: Yeah.

[Bobby Rio]: Like I gave you the example earlier where I was pretty anti… I don’t want to say antisocial. I mean, college is when I first discovered pickup material, back in ’98. And my college years were great, but then when college ended and I lost my huge social circle that I had developed, I went back into like a mode where I felt like a fish out of water and I had to learn. And what I did back then, like I mentioned earlier, was I got a job waiting tables because I knew it would force me every single day to interact with people my own age, girls…

[Angel Donovan]: Yeah.

[Bobby Rio]: I was crazy back then. I went to like 10 different restaurants in the area and I worked out the one that had the best girls. I was like, “I’m going to find a place that I want to work at.” I sent applications in to 10 places on Friday nights just to see what the staff was like, and I picked the one I liked the best and that worked. You mentioned salsa, joining a club… Make it so you have to do it.

[Angel Donovan]: Yeah, you’re like, I mean, we talked about two areas I guess, like you talked about work, get a job, which is social, or take a class, which is social, right?

[Bobby Rio]: Yeah.

[Angel Donovan]: Education. Those are two pretty good scenarios, very straightforward, and you can’t go back, right? You’ve got a job, you don't quit and you don't cut your class, you can quit your class, you can quit your job, but really, the easier thing is just stick with it and become social naturally.

[Bobby Rio]: Yeah, it’s a lot easier than saying, “You know what? I’m going to go out and stop five girls on a street today,” because they’re probably not going to do it. I hate to be pessimistic but if you’re antisocial or you’re a shy guy, you might go out on the street and stop one girl and practice, but you’re not going to do it for a week strait. Whereas if you get a job or you take a class every Wednesday night, every Friday night, whatever night it is, you’re going to have to be there, and over the course…

It might not happen overnight, but what you’re going to find is that six months down the road, especially if you’re learning it, you know, like you’re going through a conversation program and you’re actually… Now you have an environment to practice in. So now you take the material out, every Friday night you’re at work with these girls, and you just practice. You’re going to find that six months down the road, this stuff’s going to be coming natural to you. It’s going to be real. It’s going to be happening very quickly.

Like the thing with it is, and I think it’s just that most things in life whether it’s working out or making money or improving any area of your life, it happens exponentially. It’s like you struggle, struggle, struggle, and then all of a sudden you don’t even remember what it was like to be struggling. You’re like, “Holy shit, this is just easy now.”

[Angel Donovan]: Yeah.

[Bobby Rio]: And you look back and you’re like you can’t even really remember where the change happened because it just happened naturally.

[Angel Donovan]: Mm-hmm.

[Bobby Rio]: And yeah, by putting yourself in a position like that, I mean, that's the best thing I could recommend guys listening.

[Angel Donovan]: Totally. Excellent advice. And for anyone listening who’s in that kind of position, just take that first step. That's all you’ve got to do. It’s the hardest thing you’ll do but it’s really that easy. You just book the course, you get the job, go looking for the job, and you’re path to success has already started.

Okay, so what I wanted to do now is like talk a bit about Bobby Rio’s lifestyle, like dating lifestyle, because we’ll get into this studying and learning, but we’re headed in some kind of direction and that's different for each of us. So let's find out what kind of direction Bobby took himself in. So dude, what is your dating lifestyle today? How is it?

[Bobby Rio]: At the moment, I’m in a very happy relationship, the Colombian girl that I had spoken of earlier, generally just living the lifestyle that I sort of imagined. Back in college, I was an English major. I wanted to be a writer back in college. And sort of what I imagined my life to be like was sort of like a romanticized vision of Ernest Hemingway’s life. We’re just traveling and writing and just being free and being with the girl that I want to spend time with. And that's generally, I mean, knock on the wood, that's pretty much the life I’m living right now, traveling with my girlfriend, and just things are going really well.

[Angel Donovan]: Excellent. Excellent. So did you kind of go through phases along the way? Now, we’ve been seeing you’ve been kind of studying this stuff since 1998, which is a hell of a long time. So did you kind of go through different phases? How did it kind of go over the 13 years or so?

[Bobby Rio]: Yeah. Yeah, it definitely went through phases, and I guess I can do a quick sort of breakdown for the guys listening of how it worked out for me. I got to college a virgin who had never even kissed a girl. Well I should say that I kissed one girl who was extremely ugly in a garage of somebody’s house in high school and it was like the most humiliating thing. I had to like listen to my friends make fun of me for years or months about it. But the worst part about it was that I was actually happy it because it was the only girl I had kissed.

[Angel Donovan]: Yeah.

[Bobby Rio]: So even though I was getting made fun of because she was ugly, at the same time like I enjoyed it and it was the only girl… I think that was the end of junior year, and then that was it. Up until I got to college, where in college I met a girl and got into a relationship with the first girl that I kind of hooked up with in college, because I was just aching, you know, just to kind of have that affection from a girl, and it was a horrible relationship for about a year and a half. I shouldn’t have been with her but I was just scared to be single again.

And then when I did finally end it with her, that's when I discovered Ross Jeffries and the whole Speed Seduction thing, and I got a couple of my friends involved and we got into it pretty hardcore for a while. And now—we really tore it up for about a year. To be honest, not to kind of discredit… I personally didn’t find the NLP sort of stuff that I was studying… It just wasn’t my style.

[Angel Donovan]: Mm-hmm.

[Bobby Rio]: But a lot of the attitude stuff that I got from the newsletters of his that I was reading really changed my mentality about women and sort of seeing myself as more of the prize and not being the nice guy and all those kinds of things that we take for granted when you’ve been in a community for a while. When you’re hearing it for the first time, it’s really mind-blowing.

[Angel Donovan]: Yeah.

[Bobby Rio]: And for the next year I really just tore it up in college, and I wound up, again, now meeting a girl who I did really, you know, the homecoming queen of Montclair, a girl I had a huge crush on, and wound up dating her and then kind of got into a relationship with her. Stayed with her for a couple of years, and then college ended, and that's the point where college ended where I talked about how now I was sort of a fish out of water again, and that kind of brought me not back into the community per se, but it got me back into that mindset of, “I have to go out and learn this all over again.” And between getting a job as a waiter and just getting back out there, I’d say most of my 20s, it’s just a blur of drinking and partying and meeting girls until recently, when I met my current girlfriend. I mean, in between there I’d say I dated a handful of girls. Probably three to four months max were most of the relationships, before my current girlfriend, who I’ve been with for a couple of years now.

[Angel Donovan]: Okay, great. How many girls have you slept with over that time? Is it a lot or…?

[Bobby Rio]: Yeah, I mean, to be honest, I don’t have a number. I would say between 60 and 100 maybe. I don’t really know. I stopped counting in fact towards the end of college.

[Angel Donovan]: Yeah, yeah. And just for guys listening, that's pretty normal. Guys stop counting after a while. So like about your situation today, or actually like about the two situations, you know, where you’re dating, just kind of seeing lots of girls and your situation today, is there anything you liked about it and didn’t like about it, and would change or have aspirations to change for the future?

[Bobby Rio]: I mean, I don’t know how old you are or… I mean, I’m 33 years old and…

[Angel Donovan]: Yeah.

[Bobby Rio]: You know, I’m at a point in my life where—don’t get me wrong, there is the hunger and the drive and the human nature of wanting new girls and the hunt, the thrill of the hunt and the thrill of the chase. It’s always there, you know. It’s hard to suppress it when you’ve reveled in it for so long. But I’m very happy and content with where I’ve been. I mean, I’ve lived quite a bit and, I mean I guess to answer your question, are there things that I would change? Not really. I mean, I would have loved to not have had a girlfriend towards the end of college as much as I was happy with her at the time.

[Angel Donovan]: Yeah.

[Bobby Rio]: You know, I do think that college is not the time for a serious girlfriend because there's just such… I mean, maybe just now that I’m a little older and seeing going by a college campus and just wishing I was back there with the 19-year-old, 20-year-old girls.

[Angel Donovan]: [Laughs]

[Bobby Rio]: But to think about that, that would probably be the only thing, you know, happy as I was at the time with the girl, I was just hitting my peak.

[Angel Donovan]: Yeah.

[Bobby Rio]: You know, after I started studying that stuff and I was sort of on a tear, and then to kind of get into a relationship, you know, I had unsettled business of girls back then that I would have liked to have conquered. But other than that, after college, I mean I had to settle down because if not, careerwise, my nights were like Tuesday nights out partying till all hours of the night. And back then I was a realtor for a while and I’d come in… It just got difficult. My point is that, no, I don’t regret anything. I’m extremely happy with my situation.

[Angel Donovan]: That's great to hear, man. And thanks for this call. It’s been really instructional. We’ve covered a lot of topics. I’m not sure how long we’ve been talking for. I’d estimate about 50 minutes of interesting, if that's pretty close to the mark. So yeah, it’s been great talking to you, man, and having you on the call. Thanks for letting us know a bit about your personal lifestyle as well, which isn’t always easy for guys.

[Bobby Rio]: No problem, man. It’s good talking to you again.