Dating Younger Women, How To Be Cocky & Funny


Davie DeAngelo,

I have had your book and newsletters for almost 2 years. Yesterday I sent away for your advanced series. Your material is quality and obviously the way to go (I’m ridiculously cheap and I wouldnt have spent the extra money on the advanced series if i knew it wouldnt work)

My most recent story goes like this: I was working and met some female (9.0 on my scale) exactly the type of face i like. She had a hard-to-get personality. I teased her and had some good conversation for a few minutes. She had to go but returned a while later asking ‘what time it was’ or some stupid question like that that you can ask anyone and still look casual. (typical of girls i have busted on to come back and ask some stupid question) I continued to bust on her and maintain my uninterested/laid back mood.

I told her to write her number down, she did and she told me ‘she liked me’ or some pick up like that, i said “yeah i like me too”

She wanted to do something later, I said ‘like what’ (just seeing where she was coming from). She smiled and didnt really answer, to which i followed up with “whatever, you couldnt handle this”

I had a friend come by who i work with and she started talking to him ‘acting’ interested (i assume to see how i would handle it). So ignored them and went on with my stuff, instead of cock blocking i bragged a little about him.

she said she had to leave and was standing right in front of me for a couple seconds so i just moved in for a kiss and she did also (btw that was after less than a total of 15 minutes of talking). She left and I went back to my work, but not before a little 3-second Conan O’Brien dance behind my desk. earlier she told me to call her that night so i called her the next night.

That night she wanted to get busy and I would keep backing up when she went in to kiss me and didnt act too thrilled about the whole occasion. She took her shirt off right after she got in my house and i told her to put it back on and that she could take it off later. that night she said “Your the only guy who I can’t figure out” and “I’m so lucky to be here with you” and even “How come you picked me, you deserve so much better” This beautiful, hard-to-get girl’s personality changed right in front of me. And i used the beautiful “just say please” line once again.

I love you Dave (but not like that you sicko!)

-D from CA


Great story.

You’ve mentioned a couple of my favorite types of “comebacks” to things women say.

In one situation, she said, “I like you” and you replied, “I like me too”.

In another, she mentioned that she wanted to do something later with you, and you replied “Like what?”… and then said “Whatever, you couldn’t handle this”.

You TOTALLY get the equation:


In your first comeback, you’ve taken something “nice” that she was saying about you, and turned it into a perfect opportunity to dial up the tension in a funny way.

“I like you”… “Yeah, I like me too”. Classic.

In your second comment, you really add one of the “magic ingredients” of ATTRACTION called being a CHALLENGE.

Most women have never had a guy say something like, “You couldn’t handle this” to them.

It’s so surprising to a woman when she hears this kind of thing… and it’s INCREDIBLE when it’s done in a FUNNY way.

Unless you understand the dynamics of how women become attracted to men, this stuff doesn’t make any sense at all.

Remember when you were a kid and you had those little cars that you could wind up by pulling them backwards on the floor… then when you let go they would spin out and fly forward?

You could feel the tension building as you pulled the car backwards… winding it up. And when you let go, it would scream out of your hand. I always thought those were pretty cool.

Well, there was another great lesson in those cool little cars: You need to dial up the tension before you can release the energy inside.

Your story and comments do a GREAT job of this.


David, I, like you, am a slow learner with women and I own nearly every product that you sell (which i am incredibly grateful for). And proof of my learning about women came just the other night. I had been achieving mild success with women but nothing to sneeze at.

Anyhow, I was in a strip club with some friends (fyi…i HATE strip clubs, seriously) just chatting it with some people i hadn’t seen for a long time sittin in sniffler’s row with my back cocked to the side, halfway ignoring the “dancers”. So, I held up $3 for a beer just as the dancer was coming my way and right before she got
in my face i notified the bartender for a Bud Light, then turned away. This, obviously, pissed her off.

I continued to sit relaxed, just chillin, ya know. Ten minutes later she comes out in somewhat normal attire and sits right next to me and starts in with how I am an a**hole and she hated me. I just smile demurely and say, “Well i’m glad you could determine that in the first 5 minutes rather than waste your time” and did NOT look away until she did. Then, not 5 minutes of conversation later, she confessed to me that she hated me yet was “so attracted to me” she couldn’t explain it.

At this time i am like “wow, this sh** is like magic”. Next i am making out with her in front of the ENTIRE bar after she had bought me 2 beers and 2 shots. Meanwhile, this tool of a man that had tipped her in excess of $200 that night was groping her while we were playing volley-lime with our tongues. Holy sh** were all the dudes in the club impressed and needless to say she left with me to finish the deal. I went from nobody in a club of perverts spending big money to the stud that left with free alcohol and the hottest stripper there.

I always was a believer in you, David, and the other night just reaffirmed my beliefs. Talk to you again soon…… D the Cunnilingualist SoDak


What can I say?

I’ve already thought of a few things…

1) Use protection. Lots of it.

2) Don’t marry her, no matter how good the sex happens to be.

3) Wipe that DAMN Sh**-Eating-Grin off of your face already. It’s bad enough that every guy hates you… lol.

So, when you’re finished playing with fire, do yourself a favor and test out your skills in a bookstore, art show, or other place where you might meet more “quality” women.

Oh, and shut up.



Your material is great! I went to this library in town where this very beautiful woman works. There are about 6 women that work there (no men). This woman has had very wealthy men date her and policemen and a body builder etc. I’m 49 and bald and don’t make a lot of money but she has fallen for me!

Every time I’d go in there I’d get cocky and funny with all of them and this woman wants to date ME! So we’ve been dating for a couple weeks now and she’s really falling in love with me.

Her birthday was about 5 days after we first met and I didn’t buy her anything. She obviously finds this very attractive that I feel confident enough in myself that I would do that.

Last night she said she loved me for the first time. I held my ground and refused to be intimidated into saying I love her too. She was flabberghasted when she asked: “Don’t you love me?” I said I need to know her more.

This morning she went to town and got me a pop and pop corn and wouldn’t allow me to pay her back and she brought it to me.

I’ve never been able to do this before. I was always the very nice and shy guy.




Well, it’s OK to be a nice guy. Just do it in a way that doesn’t make women use the WORD “nice” to describe you.

The fact is that when you’re being Cocky & Funny, you’re actually being VERY nice… and women know it.

They love the fact that you’re paying attention to them in a way that’s INTERESTING, entertaining, funny, and unpredictable.

Good for you. Sounds like you’ve met a great gal.



I have emailed you before with a success story but this email is more of a reply to the guy who felt his age of 37 was an issue with girls in their 20′s.

My thought on this is age is only a barrier if you choose to make it one. Sure there are girls out there where they have a problem with an age difference. To me these girls are looking for someone to settle down with, bring to her parents for Sunday dinner and have the approval of her friends and not someone to date for sake of dating.

I met this Latin girl at my gym who on a scale of 1 – 10 is about a 9. After an aerobic boxing class we went out for a cup of tea. We talked and I did a little C&F and she said to me before I leave remind me to give you my phone #. I didn’t even get to ask for it but that’s OK.

The other day we were at a Wendy’s for lunch when she told me I was incredible. She went on to say I don’t crowd her I give her, her space. Keeping the C&F going I told her I agree I am incredible. I told her if it wasn’t for the fact I like girls so much I would give myself a hug and kiss.

Well, Dave, we have been dating a few months now and about the age thing she is 27 and I am 56. It was on our second date when she asked how old I was and without any hesitation I just said 56. Just being honest and straight with her. Now, granted I do not look nor act my age for she thought I was 36 or so, I am into Hip Hop & Techno music and started taking Salsa dance lessons, there are a number of Latin clubs here in Miami.

So age is only a number to me and a lot of the girls I have gone out with. When a girl I date tells her girl friend how old I am the girl friend thinks her friend is dating this old man until I meet her and she doesn’t see an age difference any more.

N. Miami Beach


Great points.

I know many men who date women that are 10 or even 20 years or more younger.

I read an interesting statistic that men who get divorced wind up marrying women that are an average of 10 years younger the second time, and that one in five men marries a women 20 years younger the second time.

Thanks for the email.


Dear Dave,

Your stuff is right on target…It took me a week to buy your ebook which is well worth it!! I don’t even think a genie could have given me better luck with women than the things you teach in ~THAT~ book. Anyway onto my SUCCESS STORY…

I’m 5’9″ weigh 140 pounds normal teenage acne problems nothing too big. The thing that got me down is I have kind of a big nose which brought my self-esteem sky rocketing downwards and kept it there for the 18 years I have been alive. Your newsletters alone gave me the confidence I needed to approach a woman.

Well make a long juicy story short. HOT woman bumps into me at gym. I ask did you grab my ass and really crank up the ball busting and C&f routine …a week later I (had sex) for the first time before I even got my first kiss. LOL. And to all you idiots who ask dumb questions before you read the book…well…you’re idiots…Thanks Man!


Hey, good job.

And I appreciate your plug for my book.

I also wish that more guys would invest in themselves and get my book before asking questions.

The questions would be so much better, and the answers would as well.


Hi Dave.

Im not gonna say that you’re a god or anything, but you are a good guy who seems to know his stuff. I’d be a 21 year old virgin right now if it wasn’t for you. I began reading your emails about 9 months ago, while trying to figure out why my last girl left me before we even got into bed together. Your book made the answer painfully obvious. I was just too nice to her. I did everything to please her, and in the process ended up tuckin my balls between my thighs.

After downloading your book, my success has come about gradually. I’ve just been gradually being more open with women, less worried about offending them, and saying even rude or controversial things to them just for laughs. Like I said it takes time to get use to doing this, but I really put it to use well with a girl I met this summer, and wow. I was amazed at how easy it was to get a reasonably attractive woman to sleep with you. Well that one didn’t work out, but I don’t care cause I’ve had more success with others since. Rock on Dave.

B from Michigan


This is some good stuff.

It’s important to test these ideas out until you become comfortable with them… and for some guys it’s VERY unusual or uncomfortable to say “rude or controversial things just for laughs” when it comes to women they’re attracted to.

Most guys fear that if they say the wrong thing, a woman won’t “like” them.

The problem with this kind of reasoning is that women don’t like men who PUSSYFOOT around looking for approval.

So by winning, you lose.

And yes, women like sex too.

They tend to enjoy it more with men who act like MEN, and not men who act like WOMEN.

Thanks for your email, and Rock On yourself, dude.



I have been receiving your emails and bought your book, and I think I’m starting to get it. I am practicing to learn a new skill now, so that I can remain “in character” as cocky and funny, while I work to assimilate the approach into my personality. A recent newsletter helped me overcome my fear of being direct with women. I always was afraid to make a move because I figured the attractive ones were already married, hooked up, or lesbians.

I thought I would be embarrassed and feel stupid if I made a move on someone who isn’t available. You said simply ask “Are you single?” I agree that it does say all the right things. So last week I tried it, and the woman was married. But I could see she was complimented, and I felt good about the exchange. The next time, a woman said she was dating. Again, it was a positive experience.

Then yesterday, a hot woman came into my office, and she seemed to be getting into me. So I asked her if she was single, and she bent over backwards to assure me that she was. Then I shocked myself when I took it a step further, blurting out “Well, but are you straight?” This knocked her for a loop — and as she insisted just how straight she really is, I noticed an immediate increase in her feminine behaviors. So I busted her again, “Well, I just couldn’t be sure.”

Thanks, Dave. I do think I’m starting to get it… T.



Yes, you are demonstrating that you’re starting to get it. By the way, once you get a woman on the defensive (in a fun way, like you did) it’s always fun to keep going… and accuse her of all kinds of crazy things.

After she said that she was straight, you could have said, “OK, that’s good. But can you cook?”.

Once you’re on a roll, stay with it. These first moments present an amazing opportunity to turn up the heat and really amplify the ATTRACTION.


Hi Dave,

Love your stuff and these e-mails. Really informative.

I’ve a couple of points about the last set.

1) NLP can work in some cases but usually as a back-up to your stuff. Women love it AT THE RIGHT TIME but use it too much and you sound wussy. DON’T give up the cocky-funny approach EVER in a relationship. Keep the woman guessing, unsure and bust other women while she’s around you. You don’t have to be trying to pick up women while she’s there, just teasing shop assistants, waitresses, her friends, etc. shows her you’re in control and attractive to other women; they won’t want rid of you then……. ever. They love it and it keeps them on their toes. It makes you unpredictable, confident, assertive (in a positive way) and not needy and wussy.

2) One 37 year old guy in a previous e-mail said he felt he couldn’t approach younger women. He didn’t want to be thought of as a creepy old guy. Well, I’m 48, split 3 years ago (I’ve 3 kids!), thought my world had ended and I’d no future. I could’ve retreated to a lonely cocoon-like existence but decided, “What the hell it’s my turn now!” This really pissed off my ex-wife who wanted to split! I began to study everything I could find on women, how they thought (or didn’t think), what made them tick (or didn’t), why – to us guys – they were so irrational, the “let’s just be friends” thing, etc.

The only thing I’ve found that REALLY works is your stuff (I’ve had the book for ages). I have had loads of success with younger women (20s and 30s). My current girl is 34, attractive and I feel like a million dollars when I walk into a club or bar with my piece of arm candy (other women never stop looking and you know they’re attracted to a guy who can pull younger women, they’re curious, it’s amazing). She says this is the best relationship she’s ever had. So, my advice to older men is ignore everyone, go have some fun, approach who the hell you like, just use the cocky and funny routine and you WILL succeed more than you’ll fail. Life’s too short so get out there and enjoy. I wouldn’t have believed it could be like this.

Thanks for everything and helping me get a life back.

J. Edinburgh, Scotland


You’ve made some great points here…

Let me comment on one or two of them.

One thing you mentioned is demonstrating how you can control situations with women… so that the woman you’re with KNOWS IT.

It’s always interesting to me how COMPETITIVE women are.

And there’s nothing quite like a woman knowing that her man can meet other women whenever he wants.

In fact, I’ll bet that a large percentage of women who stay in bad situations with men are only there because they know that their man can go meet other women anytime he wants, and they just can’t deal with the jealousy that it triggers… so they stay.

I know this doesn’t make much logical sense, but hey, it’s reality.

Now, as you know, I really don’t like the idea of “manipulating” women by lying and playing with their emotions for your enjoyment.

But if you naturally like to have fun with other people, and your girl just happens to be there when you’re joking around with the girl behind the counter at the coffee shop, then you’ll probably get some big benefits from it.

You also mentioned that when you decided to start learning about how to be more successful with women it pissed off your ex.

That’s pretty typical.

I mean, let’s face it… just between us guys… you probably allowed yourself to become a pretty boring, predictable husband… lol. So now that you’re getting your game together she’s thinking to herself “That JACKASS! Why didn’t he act like this before?! Now other women get to enjoy the part of my man that I always wanted more of!”.

A lot of guys write me to ask how they can get their ex-girlfriend back. The reality is that the reason she probably left you is because you had NO GAME. You were about as sexually interesting to her as Homer Simpson. If you want to get her back, go learn how to make women feel ATTRACTION, and then date other women. And if it’s possible to fix your relationship, that combination usually does the trick pretty nicely.

Finally, I agree with you about approaching the women you find attractive.

Look, no one is going to live your life for you.

No one is going to go meet attractive women for you.

You need to take control of your own life, and meet the kinds of women you want to meet.

Thanks for the reminder.

…and if you’re reading this right now and you’re thinking “Yea, that’s what I need… to take control of my life and my success with women”, then guess what?


You do.

And if you’d prefer to save yourself a few YEARS of trial and error (or more), and a lot of MONEY and TIME, then I suggest you check out my online eBook Double Your Dating.

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I’ll talk to you again soon.

Your Friend,

David DeAngelo