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I'm Bobby Rio, one of the founders of TSB. I tend to write about what is on my mind so you'll find a mix of self development, social dynamics and dating articles/experiences. I am fascinated with improving our general well-being. It can be done. It must be done. Find me on Facebook, lets talk more.

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What have we done here? We’ve conveyed the exact same information, but we’ve texturized it with some personality. We’ve made a little game of getting it out of you. There’s a whole mess of other things going on in here - subtle frame control, screening and qualifying - but most importantly, its made the conversation, and the process of sharing information, a lot more FUN.

These exact conversation fragments happened with a bootcamp client not long ago; needless to say, after coaching him on how to rock the second one, he was doing a lot better wit dem ladiez.

I want to add too – you don’t have to be a dancing ape with your delivery on this one. Too often, our models of fun behavior and delivery are guys who are way over the top, act gay, or have some other presentation style that just smacks of “seduction community.” You can be totally chill, and as long as your delivery includes some warmth and a smile, you’ll be golden. Think Happy Californian Stoner/Surfer.

Ok, so let’s consider another example… a girl asks you what you do. This is literally the first question out of the mouth of every girl you meet here in NYC; there must be a book that girls receive when they move here, about how to tell if the guy they’re talking to is going to treat them to Per Se dinners and weekends in the Hamptons.

I used to answer this question in one of two ways. One option was to say “Are you qualifying me already?” which girls usually take as offensive and which, 95% of the time, shuts down the conversation. That line works with certain girls, but there’s no algorithm for knowing which – you just need to practice and develop a feel for it. The other thing I’d say was something like “I’m a garbage man,” which is obviously a lie and which, because I’m not being truthful, punished them for asking me about myself. So what’s a fun way to stand out when a girl asks you this question?

F: So what do you do?

M: Hmmm, I’m a…. guess what I do. (she’s going to have to work harder than her lame ‘How to Separate the Duds from the Studs in NYC’ guidebook told her she would)

F: I don’t know. It could be anything. (and she’s not pleased about it!)

M: Ok, tell you what… (thinking)… I’ll give you three options. (I wouldn’t play a “reward/punishment” game here if its early in the conversation, as you’re getting away from the question at that point).

F: Ok, that sounds good.

M: Ok, option 1… I run a beverage company that produces and markets caffeinated gelatin shots in little one ounce packets. (lots of detail, fun, interesting)

F: Ahhh, ok…

M: Option 2: I consult with men on their lifestyles and communications skills – kind of like Hitch – to help them meet cooler women and have better social lives (too ridiculous to be true – or is it?)

F: hahahaha, right…

M: Option 3: I run a software company that builds security software for biotech firms who want to protect sensitive data from being stolen by insiders (sounds legit, too complicated to be a lie)

F: Okkkkkk… that’s tough.

M: I know, right? But you’ve got the power of your copious intellect.

F: Haha, so I’m going to guess option 3.

M: Wow, you’re like… kind of right! You get partial credit! That deserves a hug, but no kiss on the cheek yet. (give her a little hug)

F: Wait what do you mean partial credit?

M: Well… I’ve actually done all three.

F: So you’re an entrepreneur!

M: Yeah, exactly. Damn, you’re wicked smart.

And so on. This is a conversation I have, frequently almost verbatim, and helps me avoid talking about the coaching stuff because I’ll steer it into talking about jello shots or software. Of course, the way that you present something like this may vary; one way you might want to present it is to throw in your job, described very interestingly, along with two hobbies, described as if they were jobs (i.e. if you play guitar you could say “I’m a musician working to get his first breakthrough demo track laid down).

Now, its time to ask the girl what she does. Here’s the flat, boring version:

M: So what do you do?

F: I’m a technical designer for Jill Sanders.

M: Ok, uh… what’s that?

I meet girls every day and they tell me they do something that I’ve never heard of. More often than not, I just don’t have anything good to relate, immediately, to what a girl does. So what can you do with that?! Well…

M: So what do you do?

F: I’m a technical designer for Jill Sanders

M: Wait a minute, no you’re NOT. Get, OutOfHere. (smiling as if she just made your day when she told you that)

F: Wait, why (she’s probably smiling now too)….?

M: Actually, I have no idea what a technical designer is (both laugh). But it sounds exciting. Tell me about it.

Same information, more texture, more playfulness. Let’s consider another example, but with a more common job:

M: So what do you do?

F: I’m a sales representative for [insert big faceless company here]

M: Wait a minute, no you’re NOT. Get, OutOfHere. (smiling as if she just made your day when she told you that)

F: Wait, why (she’s probably smiling now too)….?

M: Ah, I’m just messing with ya. How’d you get into sales?

See? Creating this playful tension, this texture, makes a girl feel much better about sharing information with you. She has FUN telling it to you because the conversation itself is a little series of surprises.

And ultimately, this is what flirting is all about. We’ve barely scratched the surface in terms of all the techniques you can use to flirt. But if the attitude you take with you into your interactions is “what would give this conversation some texture, some fun?” then you’ll find yourself flirting pretty effortlessly.

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