How Long Should I Talk To A Woman Before I Ask For Her Phone Number? Should I Be Direct And To The Point Or Should I Flirt With Her For A While First?
This is a GREAT question. And the answer depends on the situation.

If you're in a bar, and the girl standing next to you starts up a conversation, then it makes sense to move right into the flirting and the Cocky & Funny attitude.

But if you want to approach women and get numbers or e-mails quickly, especially if she’s busy doing something else (like shopping), then you need something a little different.

I personally think that you need to convey the direct, matter-of-fact air of "this is the most NATURAL thing in the world."

If YOU act like it's normal and natural, then SHE will too. If you act uncomfortable and nervous, then she will do that too.

Most guys are very nervous about approaching women and starting conversations with them. They get all uptight and start acting sketchy at just the THOUGHT of walking up to a woman and asking her for her number.

Realize that women WANT to meet men, they WANT men to approach them… and they want guys who aren't acting nervous and insecure. Right?

So be direct.

If you'd like, you can use the One Compliment approach: Give her a compliment to start the conversation (but don't give her any more for a LOOOOOONG time).

Pause to create an air of mystery.

Try: "Hi, you are... beautiful and I had to take a moment to meet you."

The pause is priceless. Look directly into her eyes as you talk and as you… pause. This communicates that you're NOT AFRAID of her.

Then make small talk for a minute. Ask her name, ask her if she's from the area, etc. Then use the Three-Minute E-mail/Number technique.

The objective is to get her information, not to start a long dialogue.

Now, if you want to ask her to coffee right on the spot, then you might want to be Cocky & Funny right off the bat.

Remember: There's always time to show off your Cocky & Funny charm the next time you see her.
What Advice Do You Have For Guys Who Feel “Unnatural” Using Your Material? How Can They Overcome This And Get Started?
Well, the first thing I want to point out is that at some point in your life EVERYTHING felt unnatural to you.

This is just another skill that you're going to need to learn.

Don't let the idea that you've been shy up until now lead to a mental block about the issue. Just get out there and practice and work with the materials.

Next, it's probably a good idea for you to start ONLINE.

The dangers of a lunch date and what happens to a reader when he lets his guard down…Finally, make friends with a couple of guys who are good with women, and WATCH what they do in person. You'll learn a lot by combining what you've learned with the real-world experience of watching guys in person who are skilled at attracting women. This combination should help you get up to speed much faster.
Is It OK For A Guy To Ask A Woman Out On A Lunch Date?
When you "ask a woman out on a date," you're basically saying: "Hi, I'm interested in you in a romantic way and I'd like to buy you some food so you'll think of me as a wonderful provider. Then maybe we can go out on some more dates that I'll pay for and then we'll get into a relationship... if I'm lucky, you'll accept me."

Duh.

Instead of asking a woman out to lunch, tell her: "Hey, I'm going to get a cup of tea. Come along and entertain me. And I don't mean with that usual boring stuff that you talk about."

It sounds to me like you're probably LEANING into women and putting STRANGE EMOTIONAL PRESSURE on them in a very subtle way when you're "asking them out."

Stop that!

Lean back, and use what you're learning here from me.
Reader’s Question
Your advice has helped get this thirtysomething guy back into the game after
a long marriage and a painful divorce, and I really can't tell you how much I appreciate it. My interactions with women have moved slowly from awkward and self-conscious to more fluid and fun. I actually look forward to meeting new women instead of being afraid.

Your recent newsletter really made me think about a mistake that I made and wasn't able to identify until I read it from you.

I was getting boring! Now, you have to cut me a break because I was basking in the sweaty afterglow of some of the best afternoon sex I ever had in my life with
this hot and wild vixen, and the blood had not yet fully returned to my brain. But she really caught me with my pants down (literally and figuratively). While we are laying around naked on the hotel bed (which she paid for), she started to really grill me without me being aware of it.

I got all the questions that I had previously been good at putting off in a funny way. Within minutes, it seemed she had me talking about my ex-wife, my kids, my job, my family... all the stuff I had been avoiding with humor, to some extent, to keep the mystery alive.

When I got back to work and read your newsletter, I realized that all the hard work that I had done was messed up and now she got all that info in a flash. I feel I kind of blew it with her. She is out of town for a week now and I am not sure how to react. I told her I would see her when she gets back, but now I wonder if I should do some damage control and call her.

Is it OK to just go back to being Cocky & Funny and act like I didn't notice my slip? Or should I give her a hard time about grilling me when my defenses were down?

Believe me, I am happy to have been in the position I was, but not happy to have lost my "game" in the afterglow. Is this moment of weakness common? Any help is appreciated.

E.J., Chicago
My Comments
You're cracking me up over here.

I know that I'm laughing at your expense... but hey, it's better than laughing at MY expense.

I'm actually not laughing at YOU, I'm laughing at your situation. Very typical, actually.

Women test men. We all know that. But it's so easy to FORGET this fact, and not realize that it's happening when it is.

Remember: A woman wants to feel secure that you're not just "pretending" to be a cool, calm, cocky, funny, in-control guy. This is why you'll get tested in many, many ways... at many different times.

You will probably be fine.

Just go back to being a MAN, and stop asking questions like: "Should I give her a hard time about grilling me when my defenses were down?"

That's wuss talk.

If you've done enough of the RIGHT things, you can slip a few times and do a few wrong things. Just don't make a habit of it because she'll be gone in a flash.

And by the way, DON'T BE BORING! It is one of the biggest mistakes you can make.