The “Role Playing” Flirting Technique

DatingFlirting > Role Playing
by Jon Sinn • Updated: September 08, 2022

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Jon Sinn here, with another information packed article on conversation and flirting secrets.

Today I’m going to be talking to you about one of my favorite tools for flirting with a woman and getting her to think about you in a romantic context.

The technique is role-playing!

Role plays are really good for flirting because role plays are pure emotional communication.

Reasons Why Role-Playing is a Flirting Tool

  • They’re playful and fun.
  • They assume a relationship because you’re creating this fun fantasy role play relationship.
  • They are familiar
  • They create an “us versus them” dynamic
  • They’re not too deep or serious
  • You can verbally and nonverbally communicate while you do them.

So role plays are awesome for flirting.

When you play around like this and you create these fun, fantasy scenarios you, two, are flirting.

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Two Types of Role-Plays to Flirt With

So I want to talk about two specific types of role plays.

The past and future adventurous projection.

So we are going to start in the past, as we should, with what a past future projection is.

1) The Past Adventure Projection

A past adventure projection is when you make up a fun scenario where you and the girl you’re interested in knew each other in the past.

In my opinion these types of scenarios are a little more fun and flirty because they assume the two of you already had a relationship.


So my favorite one of these is called “I cheated on her with a Spanish milk maid”, so if it’s a group, I’ll say:

“You know girls, there’s something you don’t know, Sarah and I actually dated and I’m not too proud of this but I actually cheated on her, you know. It’s not my fault though because I did the math and statistically like this was my really only one chance to sleep with a Spanish milk maid, so I had to jump on that, but I do feel bad about it, you know, and I promise I’ll never do it again.”

At this point, one of two things is going to happen. The girl is going to play along and be like: yeah, I cheated on you with a pool boy. Or she will mock-cry or something, and now you know she’s flirting.

I like that one a lot because either she’s going to flirt or she’s not, and you know really early on.

2) The Future adventurous projection

Future adventurous projections are situations that haven’t happened yet but take place in the not so distant future.

I like to do, ones that assume relationships that are real. I don’t like to do the ones that are like: I’m going to put you on a spaceship and make you my space princess, or I’m going to put you in a devil suit and walk you down the street, because I guess like at a base, base level, psychologically something is happening there, maybe.

But for me I’d much rather make it more realistic and something that we can kind of play into.


“You know what, you’re going to be my girlfriend for the next five minutes, so we should create a whole relationship including breakup into five minutes, so we had better get started. How do we meet?”

And from there I’ll just go through this whole role play, fun, tongue-in-cheek scenario and I don’t have a specific way it goes down, it depends on the situation.

It could be in the bookstore, and I was making fun of you because you were reading Rush Limbaugh’s book.

Or I was making fun of you because you were reading Spanish Vogue, didn’t really realize it was in Spanish because you were just looking at pictures; and we were on our first date to the mall, and then blah-blah-blah.

But role plays in general, like I said, I like to keep a more serious role plays not like the crazy ones like: I’m going to swim with a shark with you and save you, like that stuff.

The best thing about role-plays like these, are that you can use them right away to start flirting in your conversations with women.

So get out there and start role-playing today!

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