How to Approach Women On the Street – Being Different and Interesting

Written by Carlos Xuma.

These are strategies in getting to meet women in different circumstances. The approaches will break down each situation into the essential ingredients.

This isn't your usual "be confident and just ask her" advice.

I'm going to give you specific goals, opportunities, dangers, approaches, and analytical details of each situation. Consider this an intensive class in meeting women and getting to the first - and most critical - step in the dating game.

Let's continue...

Situation: On the Street


You spot a woman on the street that you'd like to meet.


Get her phone number and/or email.

A progression to complete seduction is very unlikely.

However, you can try to bridge the opportunity to meet her later that evening of the same day.

This way you don't have to worry about her forgetting, and you get to build on the intrigue of the first meeting right away.


Women are all around you.

Half the people you meet (unless you work in a men's prison or live with monks in a retreat) are women.

You just have to start being more active about targeting and approaching them.


This situation is about as cold a contact as you can come up with.

You don't know her; she doesn't know you.

You have to establish trust quickly and move to getting her into an open attitude. Of course, you are also subject to more rejection, but that is part of the game.


This approach will help you immensely in any "cold contact" situation. It's called "Tease Her to Please Her".

We've all heard about being "cocky and funny," or "confident and funny," or variations thereof.

This technique uses a self-confident posture, along with humor, to disarm a woman's natural defenses so you can meet more women.

If you meet more women, you get more experience, you get more confidence, you get laid more, and more options open up to you.

If you date only a few women, you tend to cling on to each as if she was your saving grace.

This is a method of understanding how to meet women any time and any place.

All you need to do is open your eyes and set aside about 4 minutes (or less) to talk to her, (if that long).

This approach will work anywhere you see a woman, and it doesn't require you to memorize a bunch of secret handshakes or hypnotic trance words.

Tease to Please works because it short-circuits her usual defense mechanisms to meeting 'strange' men.

You see, every woman comes with her factory-installed defense mechanism against meeting new guys.

When a guy approaches her, for any reason, she assumes you're picking up on her.

It's what she's gotten used to.

All women are by now, and they all have a standard routine of being a little stand-offish to you until you bust past this barrier.

You have 3 seconds from spotting a woman to when you approach her and say something to engage her interest.

If you wait longer, your opportunity window closes faster than Ticketmaster can sell out Britney Spears tickets.

In that 3 seconds, you do this:

Look her over, and spot something about her appearance that you can comment on.

Start with her shoes, and work your way up.

Do not choose a physical body trait (like big earlobes, bubble-butt, giant breasts) to comment on.

Especially not her overall attractiveness.

You find one thing that you can key off of and say something about that will give you an inroad. This is your Anchor. Once you've found it, you comment on it to her and smile at her, making strong eye contact.


She's got bright red shoes on - "Wow, those are ... interesting shoes. My sister might like a pair like that. Where'd you get them...?"


She's got a black denim dress on - "My sister likes dresses like that. Where'd you get it...?"

(If you don't have a sister, use 'Aunt' or 'Cousin.' You shouldn't have to lie.)

She'll say something like,

"Oh, I got it at Macy's" or something along those lines.

You then nod your head and look at it for a second, as if you can't make up your mind about whether you like it or not.

At no time do you ever throw out the usual nauseating male flattery approaches, like

"Oh, that dress goes so perfectly with your cheekbones."

(There is a time and a place for flattery, and it's not in an improvised meeting like this.)

Flattery is the scream for approval of the desperate guy.

It's like cotton candy - sweet for a split second, but disappears almost immediately. You want to dangle the promise in front of her first.

You almost convey a look of inconvenience that you went out of your way to comment on her alligator-skin shoes, or her denim skirt. The less she thinks you approached her out of sexual interest, the lower her guard is. (And the better off you are.)

Be careful here:

Don't be insulting! Just be mysterious and ambiguous.

Her next mental question is:

"Gee, I wonder if he likes my dress...? He didn't say..."

From here, you will bridge into the Tease portion of the conversation, and we'll cover that in the next section.

All there really is left to do is to keep her engaged in the conversation for just a minute or two, show some confidence, and walk away with her phone number.

Now, the typical question I get is

"What if there's nothing out of the ordinary about her?"

Simple - You make something up.

There is always something you can find when you look, and if it's not readily apparent, you make it up.

If she's got clothes on (and even here in San Francisco, they still wear clothes) you can find something to pick out.

I recommend looking for jewelry, because every woman takes a lot of thought in selecting her jewelry.

For especially attractive women, you need to come on a bit differently, and it pays to use a combination of the negative-hit with this.

I even recommend that when you get used to this technique, you use it exclusively on the hotties. When you're comfortable with it, it makes more impact.

You say just one thing, and it's so easy you'll have a tough time forgetting it:

"Your dress/shoes/blouse/jacket/purse (whatever) caught my eye. I like the style, but I think you should try it in black, instead. You'd look better with it in black instead of gray."  (Choose the color accordingly.)

You nod your head, again meeting her eyes full-on.

Her head will suddenly spin. She'll think (or say):

"But ... but ... all the other guys said I look like a fashion model with this on... what do you mean??"

By using these approaches, you've just flipped her trust switch in her head.

You see, she starts out needing to find a reason to be interested and trust you - or she quickly categorizes you as a friend (FRIEND = non-lover, a woman you won't be able to sleep with).

If you just start talking to her neutrally, without sexually exciting her, she's wondering, "Is he safe?" For all she knows, you're a nut-case looking to pull her into a multi-level marketing scheme.

Now, all of a sudden, she is suddenly told (by your words and actions) that you might not be so interested.

You're different - i.e., interesting to her.

For the first week or so, if you're feeling a bit nervous about approaching women, work your way into this slowly.

Just use the intro line I gave you, and take it wherever you need.

Hell, I'd even recommend you only ask her the first part ("Where'd you get that ring, my sister might like one like that ..."), then say "thanks" and walk away.

Get used to just chatting up anyone and everyone you meet. Take the pressure off for the first week or two, until you get used to the fact that women aren't going to reject you like you think they will.

You don't need anything fancy or clever.

You don't need anything special to comment on.

You just take whatever she is wearing or holding and comment on it as if it were different or interesting.

Then, by virtue of following it up with a quick tease, you get her mind off her initial worries (Is he safe?) and defensive behavior and on to validating herself a little to you.

This is the primary psychological underpinning of the whole "Tease to Please" or acting cocky and funny method.

What most guys will do is to spend all their energy trying to climb over her initial trust hurdle, when they really need to focus on getting her to flip that switch in her head by making her the one to present herself to you.

Just remember to keep things light and humorous, and never to insult.

Now, on to the second half of the technique.

We've learned that the Tease to Please approach works because it short-circuits her usual defense mechanisms to meeting 'strange' men.

You see, every woman comes with her factory-installed defense mechanism against meeting new guys.

When a guy approaches her, for any reason, she assumes you're picking up on her.

It's what she's gotten used to.

All women are by now, and they all have a standard routine of being a little stand-offish to you until you bust past this barrier.

They act a little quiet and put out by the fact that here's another guy trying to chat them up for a phone number to get a date, to get some sex... They get a little insulated.

So now we'll break on through to the other side.

Remember when you were just an eight-year-old kid on the playground?

There were all these 'strange' creatures playing around the sandbox. T

hey were called girls, and they seemed so bizarre and alien to you. They were delicate and soft, yet interesting in a way that you couldn't quite explain, and you knew that they were Different.

How do kids treat those that are Different? They tease them.

"Mary, Mary, she's so hairy!"

"Where'd you get that backpack? Looks like a hunchback!"

"Jenny's got a carrot top!"

Boys teased girls.

Girls teased boys.

Everyone made fun of everyone else.

It was sandlot politics at its best, and you learned very quickly that you had to develop a callus to the teasing, or you'd get bruised pretty badly.

(Some kids never adjusted, and grew up with their sandbox issues haunting them for life.)

I'll be willing to bet you that you teased more girls because you liked them than you did because of any genuine weirdness.

Sure, there's some cruelty, but the first social interaction most boys have with girls is when they teased them mercilessly.

And what happened?

The girls stuck up for themselves.

They teased back.

And they didn't realize it at the time, but this set in motion a whole pattern of behavior that led to them being very interested and attracted when they are challenged.

That's right, boys. Teasing is all about raising the stakes of challenge to her, and letting her know that you don't get all mushy inside when you get near a girl.

No confidence = no attraction from her.

Tease to Please is a simple strategy.

By teasing, you emulate a lot of the self-confidence you need to demonstrate with a woman.

That's really the secret in a nutshell. Call it what you want, you are simply showing her you have the balls to not roll over and pant like a whipped dog every time a woman comes near you.

Here's how it's done:

You've just delivered your introduction.

Now you are in a position to continue the conversation as you see fit.

You've disarmed her natural defenses and opened up your opportunity to engage her attraction mechanism. You do this through Teasing.

From the example we used last time: She's got bright red shoes on.

YOU: "Wow, those are ... interesting shoes. My sister might like a pair like that. Where'd you get them...?"

HER: "Oh, these? Uhm, I got them at Macy's. They're really old. I was looking to get a new pair."

YOU: "Well, my sister is pretty young, but she'd like that style. For an old lady ... (pause) ... you're a pretty sharp dresser." You give her a slight smile that says "That was a joke."

Remember, "sister" can be changed to aunt, or cousin, or whatever.

You can use that standard response I just gave you for now, but you'll do better if you learn how to think on your feet and come up with more personal and customized versions.

There are a whole ton of teasing responses.

Here are some others you can use, delivered with that sly smile:

"Well, with heels that high, you better watch out for awnings. And low-flying planes."

"How many feet have you crushed with those things? I'm wearing steel-toes, so don't try it on me, lady."

Let's say you want to tease her about a ring she's wearing:

"Well, my sister likes those 'groovy' rings, too. Do you have a mood ring? I bet you were the kind of girl to wear one of those. Was it blue all the time? You look like you have cold hands."

"My sister likes toe rings like that. Do you wear them on your toes, too? Just don't tell me you have a weird piercing, like your butt-cheek. That would just be too freaky."

"Wow, that ring is huge. I bet you have to leave it off when you go swimming, huh? Otherwise you'd sink right to the bottom."

It goes on and on.

In fact, you could sit down and just think up a handful of these for a few different parts of clothing (shoes, purse, jacket) and/or jewelry and be prepared for almost any encounter.

Once again: Don't be insulting. Be teasing. Teasing is done with a tongue-in-cheek sense of humor.

You kid with her.

If you make fun of her in a mean or malicious way, you're out.

If you don't let her know you're kidding, you're out.

The point of this exercise is to:

  • Get her laughing
  • Challenge her (by demonstrating Self-confidence and that you're different.)

After you joke with her a little, make a decision if this is a woman you might be interested in for your seduction. If so, you smile and start to walk away. Then, turn right back and tell her (don't ask):

"Hey, you know, we might like to continue this conversation sometime. Write down your number for me." (Memorize this phrasing to use exactly.)

An alternate approach:

"Hey, you know, we might like to continue this conversation sometime. Write down your email address for me."

If she says she doesn't have a pen, you hand her yours. If she says she doesn't have email, tease her some more: "No email? You didn't just get back from a UFO abduction did you?" Smile.

"Here, just give me your home phone." (As she starts writing): "Uhm, your real number, please. I'm just going to call you as soon as I get home and leave a dozen annoying messages on your answering machine."

Smile. Take her number and leave. Don't tell her you'll call her. Leave her wondering.

That's it. You disarm her defenses by keeping a sense of humor. You show self-confidence and challenge her by teasing a little.

Then you ask for what you want, and then you leave. You're a busy guy, with too many women to meet to waste any time here.


That should give you more than enough detail on how to work this approach for any cold contact.

Be simple and direct, and most importantly, be confident with your words and manner.

This technique is used in almost every one of these approaches.

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Carlos brings to the table a variety of life experiences, including a background in relationship skills, life-coaching, motivational psychology, sales, management, Martial Arts, teaching and instruction, technology and engineering, Eastern philosophy, the psychology of achievement, and music.

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