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The Mastery Program

Day 18

Flirting skill #2: Situational Flirting

What is Situational flirting? Situational flirting is being silly with a woman about a misinterpreted situation or thing. Situational flirting uses humorous misinterpretations as a basis for verbal play.

When you are interacting with women you should be:
  1. looking for the thing in the environment you can flirt about/make jokes about

  2. looking for the silly interpretation of the situation to flirt about

These examples are not prescriptions--don't bother memorizing them. They are just to give you an idea of what situational flirting can be like. You should adapt situational flirting to whatever environment or situation you are in with a woman. Notice how all these examples are silly, and show a woman your playful side.

At St. Louis Arch, to girl selling tickets:

You: Do you get to party after-hours up in the arch?

At Gap, buying clothes, to a girl working there who has a headset on:

You: "Can you launch the shuttle with that?"


You: Are they feeling you pro-gap propaganda through that?

Her: Oh no--I love the Gap!

You: Oh, so it's working!

Her: (Laughs)

At the bookstore:

You: Can you review the book for me? What, you mean you haven't read them all?


You: So, do you get to keep a percentage of the money that comes in--you know, as tips?

Her: I wish! (Smiles)

You: Oh, then you might have to pay out a percentage on what goes out, too! That would be bad!

Her: (Laughs)


You go up to the teller, and right by her there's a glass jar with a bow on it, which is full of tootsie rolls.

You: Oh wow, a thing of tootsie rolls! Is this for me?

Her: Well, it depends, have you been good?

You: Well, I think I've been really good, but in some ways, you know, I think I've been bad.

Her: (laughs)

Restaurant that has a contest--drop in your business card and get free bread for a year

You: So, do they deliver it all at once? Are you going to come to my house with a big truck and dump a years' worth of bread on my lawn?

Her: (laughs)

To waitress, who is going to wrap up leftover food "to go"

You: I'm going to keep this forever, as a momento of our time together

Her: (laughs)

To the receptionist at the dentist's office

You: So, you are the guardian of this ba-a-ad, evil place, eh?

Her: Oh yes, I'm the guardian, all right.

You: How could I persuade you to put a spell on me to keep me from harm here? In fact, I think I can feel you putting a spell on me already. You are bewitching me. Now I feel like I can go in there, protected by the spell you have me under. I'll just say to the dentist, ‘the beautiful and charming Natalie put me under a protective spell.' How do you think that will work?

Her: You can try it, but I'd still take the novocaine.

You: Oh, I don't need painkiller after seeing you. Have you ever had the feeling of meeting someone, and it's like you heart can only feel good feelings, can feel no pain? After meeting you, I'm sure I won't need anything else.

Her: Well, thank you! (laughs)

Other topics covered in day 18 of the CD series
  • Much more general information about situational flirting

  • Places where you can use situational flirting

  • Asking for the phone number/email address: different approaches

  • Getting a card made to give to women; results you can expect

  • When to call a woman for a date

  • Rules and regulations for talking with women on the phone

  • Specifics of how to ask a woman out and how to set up the date

  • Specific homework to ease you into using situational flirting

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Mastery CD set