How To Be Cool

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When I first moved to New York City, I used to read all the time about how women wanted a guy with a good sense of humor. It was in every magazine, every talk showeven my female friends would tell me the exact same thing. Even the Magic Bullets Handbook said so, and Magic Bullets is well-known for contradicting conventional wisdom (and being right).

You'd think that a professional comedian such as myself would have no problem with women then, right? Wrong.

I noticed instantly some things that I was already doing right (thanks to my improv and standup training), but some other things that I had WAY wrong. I want to talk to you guys about one of those things right now.

Going from funny to sexy. Why is it that so many really funny comedians have so much trouble hooking up with high quality women? How to you go from being the funny guy to the guy she wants to take home?

The answer is to use humor to mask your sexual intent. That means bringing up the topic of sex, but in a funny way.


You should always be looking for opportunities to bring up the topic of sex with a woman that you are interested in, even though it can be hard to find a way to make it not creepy. When you talk about sex, you subcommunicate that you are someone who is interested in sex, who has had sex before, who is confident about sex. You start to paint the picture that sex is a normal and important part of your life.

You also start to introduce the idea of sex with the woman you're talking to, which is really important, especially if you want same night lays. She'll have a hard time putting you in the friend zone if you've already brought up the idea of hooking up with her.

Not only that, but if done in the right way, simply talking about sex can be physically exciting to her. It is a huge tool in breaking though levels of intimacy.

So how do we do this without sounding like a total creeper? The answer is above." USE HUMOR! "

One of the things I've noticed from having done hundreds of approaches is that you can get away with a lot if you are funny. If you've read any of my "On The Fly" articles, you'll see exactly how much you can get away when you are joking around with a woman. Knowing this, you should always start your sexual framing in a way that's funny.


There are literally hundreds of ways to work sex into conversation, but for the moment I'll hit you with two that are super easy.

The first is to hide it in a role play. A role play is putting you and the woman in a fake scenario that she can play along with. For example, pretending that you are breaking up even though you just met:

"I'm totally breaking up with you. I'll come over tomorrow to get my CD's and for the breakup sex.

You can even pretend that you've been married and add all sorts of crazy fake details:

"That's it! You and I are getting a divorce. Just as well. You could never handle me in bed anyways."

Once you have the fake scenario out there, you've got free reign over the kind of material you can make up. Why not make up something sexual?

The second technique has to do with one of my Disqualification types. In my Humor, Improv and Attraction seminar I go deep into Disqualification and go over the 10 different types. One of those types is called Raising Your Value, in which you boast about your positive qualities. You talk about how attractive you are, how cool you are, and most importantly, how sure you are that the woman you are talking to you is attracted to you:

"You're such a sexual predator. I can feel you undressing me with your eyes right now!


"I'd appreciate it if you'd get your mind out of the gutter. I know it's hard because I'm so hot, but just do your best and think unsexy thoughts.

In both of the above techniques, even though it's just a joke, it still breaks through those same levels of intimacy. It has the same effect, even though it's just a joke!

The above tools are a good place to start, but it really is just the tip of the iceberg. Using some of the other techniques I teach can jump off comments like those into some super charged sexual framing!

For example, did you know that these sexual jokes are a perfect opportunity to escalate physically? Just throw it into the joke! Why not have the fake breakup conversation with her sitting on your lap? Why not give her a friendly hug then accuse her of copping a feel? The possibilities are limitless if you're looking in the right places.

Of course they have to be in on the joke for this to work, so make sure you get on the same page with them as soon as possible.


Suggested free e-books to read:

Debra Benton - How To Act Like A Ceo
John Alexander - How To Become Alpha Male

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