Tag Archives: Approaching Women

Art of Rapport students get results

At last weekend’s Art of Rapport workshop, I had the pleasure to work with two very motivated and hard working gentlemen. Our Pickup 101 workshops are no easy class. When you take a workshop with us, we will push you to do things that make you nervous, because that is how you grow.

Josh and Simon and the other six men in the workshop spent the morning learning how to walk up to a woman that they don’t know, make her laugh or smile, and convey their natural personalities in a compelling way.

Josh and Simon pushed themselves to approach and meet women in ways they never had before, and it works.

Simon had a natural ease about him, but needed to get a little help sharing that personality with women.

We got to work, and he put our work into action.

He met quite a few women. Man, doesn’t he look great:


After I suggested to Simon that he talk to that woman above, I was actually a little jealous. She was very cute, and I wished that I had talked to her instead.

Of course, Simon applied the lessons from the night before, and ended up talking to this woman for about 15 minutes or so, and had a fantastic conversations. He told me later that he felt like the conversation just flowed. In fact, he told me after he excused himself that the only reason he left was that he wanted to move on and meet more women! He didn’t want to spend all day talking to just one.

So what did he do? Simon walked across the square and met another woman sitting, watching the passers by:


I was proud of Simon, and he was proud of himself. He moved through his nervousness and did something that he hadn’t done before, and he grew from it.

When Josh started the workshop, I think he had some doubts about the workshop, and about himself. I don’t think he was quite sure that the material that we taught in Art of Rapport was going to work for him.

I told Asher and Megan, the two coaches that were leading the workshop, to put Josh with me went we went out to meet some women, and I would make sure he got it :)

Of course, they did put him with me.

The first women or two that Josh met didn’t spark. We were walking through Unions Square on Saturday afternoon, and kept moving around. Eventually, I saw her, and so did Josh. I think he knew he should go meet her, and I gave him some encouragement to do that.


He took a breath, and walked up to her. I don’t know what he said exactly, but I saw her smile in response. They stood in the middle of the square, talking to each other. He was relaxed, and it showed in his body language.

I surreptitiously walked by them and took some photos with my phone, just for fun.

Then something I wasn’t expecting happened. He took off. With her. He just walked off and left Union Square, while walking and talking with her.

Turns out he left with her to go get some coffee at a cafe.

After an hour or so, I called him up and told him he couldn’t be a lover boy all day long. Eventually, he came back to Union Square, and he was different. He wasn’t skeptical, and he had a new found confidence about him.

He learned something from the workshop, and it wasn’t just a line to start a conversation with women, or a few tips. He learned something about himself. He learned that he was the kind of man that can meet a woman in the middle of the day and take her to a cafe on a mini date.

More than that, he is the kind of man that women want to meet, and would be happy to spend their afternoon with. That lesson is far more valuable than any tip that I could teach, and is something that can’t be read on the internet.

How to flirt: Use this opener to start a conversation with women

Here is one of my favorite ways to start a flirtatious conversation with a group of women. This is tons of fun, and always gets a good response from the group.

I’ve used this during the day in a park, or in Union Square, and I’ve used it at night when I am out at bars. It is simple to use, and leaves a great opening to continue the conversation.

This works best with women in groups of 2 or 3, which is pretty common to see when you are out and about.

So what is this amazingly simple line to use?

“Hey guys, you know, I’m actually not sure which of you to flirt with first.”

That’s it. You can add to it, “You’re both so cute, I’m not sure which of you to flirt with first.”

You can change it up: “I’m not sure which of you I should hit on first. This is really a dilemma for me.”

This is a fun, flirtatious way to start the conversation.

You can then ask which of them is the best flirt, if one responds really well, tell the others that you are going to flirt with her, you can accuse them of being bad at flirting, and on and on and on.

A fun attitude makes this work. This is not a very serious way to start a conversation, so there is no reason to be too serious about it. A smile and upbeat attitude goes a long way.

Last weekend I approached a two women in a bar and used this opener, and one of them responded that we should play rock, paper, scissor to see who flirts with who. I’ll be stealing that from her.

Try this out, have some fun, and flirt with some women.

She said, “We don’t like timid men”

Timid men need not apply. Women agree on this.

My interaction with a couple girls on Saturday was very rich and metatextual. A lot happened that was very instructional. I am writing up all of the interesting parts in pieces, to extract the juicy information out of it.

I was on the balcony of Medjool, overlooking the dance floor, talking to a cute girl in a hat, and she talked about the different ways that men approach women. “We [women] don’t like timid men. We can tell when a man is timid, and it kills it.”

She told me that was why she liked me, I didn’t hesitate to come over to her and her friend and see what was going on, meet them, and flirt with them. I knew what I was doing, and I knew how I was going to approach them, how I was going to start the conversation, and felt good about my ability to talk to them and join their group.

It was coincidental that this was in the middle of an Art of Attraction workshop, an entire workshop devoted to making sure men aren’t timid. It sure as hell isn’t the time for me to be timid myself.

It was nice to hear from a woman that what I teach is, you know, right.

Recognizing Timidness

Timidness is the almost the complete opposite of confidence. Confidence is being sure and comfortable with what you are doing, not hesitating, and enjoying yourself.

A timid man is cautious, nervous, hesitant, and waits for permission, or a good reaction, before going on with what he is doing. A timid man doesn’t take risks, and doesn’t do anything to put himself on the spot.

I’ve noticed that the biggest reason that men are timid when approaching a woman is the fact that they are waiting to see how they will react. They are waiting for a good reaction before continuing the interaction.

Timid men want a good reaction before committing to an interaction. They are waiting for permission to join a group of women before they really open up and express them self.

The odd thing about this though, is that by being timid, the chances of being accepted by, and receiving a warm response from a group of women will go down drastically.

“Any woman wants a confident man.”

Women respond to your confidence.

Women always seem to give the same answers when they ask what they are attracted to in a man. They like a man who can just be himself, who can make her laugh, and above all, is confident.

Confidence is one of those things in life that, like all important things, is very simple, yet can be very difficult to put into actual practice.

Here are some of the things that display that a man is confident when he approaches a group.

  • He does not fidget when he walks, and when he stands next to the women
  • He makes eye contact with the women, and does not get nervous and look away when they give eye contact back
  • He talks slowly and calmly
  • He does not seek their approval before proceeding to talk to them
  • He smiles and enjoys the time he is spending with the women
  • He is sure of how he is going to approach, and says what he has to say without hesitation

This is just a partial list, but these are some of the things that women see that indicate if a man is confident about what he is doing or not.

There is no downside to confidence.

As men, we really have very little to lose by approaching some women and starting to talk to them. The worst that can happen is that they turn us down, or aren’t interested in meeting us. It may not exactly feel that way when we aren’t used to approaching women often, but this is true, objectively.

There is nothing to lose by being confident. If you have decided to approach a woman, it will not go worse by approaching more confidently. It can only make things go better, and kick off things with a woman better.

On the flipside, being timid can only make the woman’s reaction worse. Being timid when approaching a woman will not make her like you more, and it will not make a better first impression.

We teach confident behavior and how to confidently approach a woman at the Art of Attraction workshop. The workshop is three days, spending days and evenings in a classroom to learn, and more importantly, practice the skills that make you more confident. We spend two nights out on the town, meeting and talking to women, and working with our coaches to put the new skills into practice.

The workshop is an investment in your future, your relationships, and in the confidence that you feel every day.

Please feel free to click right here and read more about it on the PickUp 101 website.

This workshop will knock the timid right out of you, and women will thank you for that.

Why You Get Nervous Approaching In Bars

I was hanging out in the Marina District one weekend. I ran into my friend Shawn, in addition to a bunch of other folks I knew.
“I still get nervous and full of anxiety when it is time to approach a girl” he told me.

Interlude: Earlier that night I was hanging out with my friend Ben, who was visiting from New York for the weekend. Ben and I decided that we wanted to have one of those nights where we drink a lot and have a good ol’ time together.

We were in the back room of the Matrix with a couple other friends, and two girls walk around the corner.

“There you are, we’ve been waiting all night for you guys,” I say to them as soon as I see them.

Ben doesn’t skip a beat, “Yeah, where have you been?”

He pulls one over to him, and I pull one over to me, and we start bantering and flirting with them. Standard protocol.

Eventually the girls left, we had a half hour of fun with them, then they went off on their merry way. Neither Ben nor I were particularly interested in these girls, we were just having a good ol’ time.

End Interlude.

So I told Shawn about what happened earlier when I was hanging out with Ben. There was no anxiety or nervousness because there was no actual approach. We were having fun, and they were there. Of course I said something to them.

When you are out in a bar or a club, there are always women around you to talk to and flirt with.

The way to not get anxious and nervous when you approach is to not approach in the traditional sense at all. Don’t stand there, think about how you want to approach her, then approach her. This is going to make you nervous as can be.

Approaching should be a lot more spontaneous when you are out at a bar or a club. If you are having fun yourself, this is going to make your interactions go all the more better. When you approach spontaneously, there won’t be a chance for your fun to turn into nervousness.

If you’re gonna go to bars and clubs to meet women, make sure you are having fun first.

Now go meet some women!

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If you are wondering what to say, or how to start interactions like this with women, check out the Art of Attraction workshop. We spend two and a half days learning exactly this, part of which is spent out in bars and clubs. In fact, if you take the workshop in San Francisco, chances are you will go to the very bar that all of the above took place at, and talk to some gorgeous women too..

CLICK HERE to find out more info.

Overdoing It

Talk to the HAND!

So you see some girls in the bar. You walk up to flirt with them.  They ask some question… “Oh my god! You guys are like inquisitive little investigators! You are like ninja investigators that strike out to find the answers you want! I am totally gonna hire you as my ninja assassin strike team and you will be sent into old ladies houses for me to steal their fresh-baked cookies! You are gonna be blue ninja, and you are gonna be pink ninja… but YOU… YOU get to be the argyle ninja because you are the deadliest. Yeah, your outfit is going to be one giant argyle sock with a little slit cut in it for your eyes.”

Wait, where are they going?



“I didn’t… overgame you… did I?”

Overgaming is when you do (or overdo) something and it is kind of weird.

Take the above example. That was a WHOLE lot of playful banter. Say, for the sake of argument, that I unloaded that clip of banter, machine gun style, into a group of women. I would hope they would start laughing and giggling and pawing at me, but if I kept it up they might start to think “well, this is fun and silly, and it makes me laugh, but this guy is kind of weird because all he does is stand there and say all these goofy things to us without stopping”.

What is really going on here is that I am bantering AT them, rather than bantering WITH them, and that is why they give me the “overgamed” response in this hypothetical little situation. You can banter AT a girl for a second, but you better get into a conversation WITH her right after that. A conversation with a girl goes by many names, but we usually refer to it as “vibing” or “rapport”. It can also be banter, but it better be banter with a girl, rather than at her.

I have had banter conversations that go on for a good half hour. The reason that these conversations didn’t end up as overgaming was that we were bantering together. We ended up playing a game that everyone was joining in on. Remember, when banter is really working, it is a two way street. If you are out at a party or something like that it is OK to banter with people a lot. You DON’T want to just hose them down with banter though, because then they will be all soggy. You want to kind of bat the birdie back and forth with banter.

NOTE: This post is a modified version to a response to a question on the PickUp Lounge, the PickUp 101 VIP discussion board.

Your Resolution for the New Year: Start Walking

Start Walking!It is the time of year for resolutions. A lot of guys who want to improve their lives (especially their LOVE lives) make resolutions around this time. A lot of men look back on their year and see that they want something to change. They are finally going to do the work to make the changes happen.

Now, New Year’s resolutions are notoriously hard to keep. I know it, you know it, and the 1,600 page copy of “War and Peace” that I read the first two pages of (after resolving to read that novel a few years ago) knows it.

I spent this New Year’s with my girl. We talked a bit about resolutions, and I told her I don’t really make any, because I can NEVER keep them. She said that the reason that people often don’t follow through on their resolutions is that they set the bar too high. She told me about a friend who always resolved to “run more”, but never did. Finally, this friend made the resolution that every day, she would put on her running shoes and step outside. This goal is easily achievable, I mean, all you have to do is step outside, right? What happened is that this friend ended up running more that year because the goal was easy to achieve, but more often than not it led to a nice jog.

Here it is, January 2nd, and I started thinking about this idea. I also have thought about one thing that I have noticed. The hardest part of any approach is taking that first step of walking towards a girl you want to hit on. Once you start walking, you don’t think about the nervousness as much, and your mind starts to think about what you are actually going to say.

Everyday, start walking towards a woman that you want to flirt with

Here’s the resolution I suggest for anybody who wants to talk to more women: Everyday, start walking towards a woman that you want to flirt with. That’s it. Resolve that EVERY DAY of this year, you will start walking towards a woman to hit on her. What you do after you start walking isn’t part of this resolution. All you have to do is start walking towards a woman every day. You just might surprise yourself.

The beauty of this resolution is that of and by itself, it is incredibly simple to succeed at. This very simple step, on the other hand, is also the very hardest step to make when looking at it as part of an “attempted pickup”. By looking at it as part of a simple goal to be achieved, you remove it from the context that makes it so nerve-racking.

I know I have to start walking towards some woman I want to flirt with on my way home from work today so I can meet this goal. Now, I know once I start walking I am gonna jump on the chance to flirt with her, and have some fun with it. I hope some of you will join in on this.

Oh, I have one other resolution, to watch all 21 James Bond movies and write up my reviews of them for my web site. I used the gift cards that my sister gave me for Christmas to buy the first two volumes of the complete James Bond collections. I don’t think this resolution will be a problem though :)

I Bet On My Students

Last night I was at a favorite Wednesday hotspot with K and fellow instructor Walter. K works in the Pickup 101 office, and he has been through our workshops. In fact, he was my student on the second night of his Art of Attraction workshop. This was the night that he got lap dances from a group of 10 women. Suffice to say, the boy knows what he is doing.

So we were having a hang out night, just chatting and flirting with the occasional group of girls. We all go out so that K and I can smoke a cigarette, and he asks me and Walter, “so what do you do when a girl is on her phone?” We look over, and there is a cute asian girl on the phone 10 or 15 feet away from us. So we tell him.

He is reluctant to proceed with the directions we gave him. She gets off the phone, and his opportunity is presenting itself. Still he doesn’t go. This is when I grabbed him, and literally pushed him into a conversation with her. She looks up, alarmed, staring at us. I tell her, “I’m sorry… I didn’t mean to alarm you”, and I left to hang with Walter, leaving K to start a conversation. I leave as he is saying, “My friend wanted me to come tell you that…”

I found out after the fact that what he said was, “My friend wanted me to come tell you that you are really cute. Actually… it was ME that wanted to tell you that.” I imagine that this was just about the time that she erupted in smiles and giggles. They were talking for a few minutes when I saw the hands. You can tell a lot about how two people feel about each other by the way their hands touch. She high fived him, and their hands stayed together, and their fingers lingered across each others as their hands parted.

It was on.

At this time, Walter said something along the lines that he didn’t think it was going anywhere. I called BS, so we made a friendly bet. I bet Walter that he would get her phone number. Loser had to buy the other a drink next Wednesday. I’ll take that bet. I know what I saw. Besides, he was MY student. I believed in him.

After a few minutes of flirting, he came back. Without her number. I told him to get his @ss over there and GET HER NUMBER. He walked back over, flirted a little more, his phone is out…

He walks back to us five minutes later, and he is saying, “OK, I’ll call you…” as he is leaving. He got the number.

I got my drink.

Life is good.

As for me, yes, I flirted with the two cutest blondes I saw that night. Good wholesome fun :)

Flirt Everywhere

(This one is for you, V)

It is important to be ready to flirt with anyone, anytime, anywhere. When I know that I am ready to flirt with a girl at a moments notice, I feel on top of the world. Electrified.

This is a little anecdote from last week. I was talking to one of my coaching clients, and I challenged him to approach a girl everyday with with the simple as syrup, “you’re cute”. I told him I would do it the next day too, so I headed out on my lunch break ready to flirt with some lucky woman.

After walking around, getting lunch, then walking around some more, I was getting disappointing, because I was really just not seeing any really cute women to flirt with.

Then I saw this adorable blonde in the Metreon. She was working at one of those little booths, selling a nail polish device or something. I walk up to her, she says, “Come here, I have something to show you”.

Immediately I replied, “You are way too cute to be selling me this. How about we just flirt together for the next few minutes?”

She giggled, I kept bantering, I vibed for a few minutes, but then she had to get back to work.

This interaction didn’t end up in a number, or a date, but that is OK. Flirting like that gets the blood flowing, gets your endorphins pumped, and makes you feel great.

Go out and flirt! Now!