How to Approach Women – Empathy and Boldness

By Marcus Neo | Conversation

Dec 30
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Countless of us walk the streets and have hundreds of girls and women who fit our physical criteria as a potential romantic partner walk by us. Yet, how many of us end up not nothing anything, day after day, months after months, and years. Let’s be honest here, you and I are guilty of letting these opportunities slip by. Have you ever wondered what it’s like to approach an attractive stranger and the realm of potential possibilities that comes after that?

Is there a system one can follow on how to approach a girl in any given social situation? The answer varies, but the underlying principles are similar.

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How to Approach Girls – The Ultimate Guide

  • Your First Impression

Psychological research shows humans base the majority of our perception of people on the first couple of minutes we spend with each other. This initial perception extends and influences our relationship to the person for weeks, and even months. So, assuming you approach a girl you’re attracted to, how can you make a good impressing upon her through your first couple of minutes in your approach?

You’ll need to be dressed minimally well. You’ll need minimally a fitting t-shirt, jeans, and shoes. You’ll also need to be well shaved, with your hair is taken care of. You’ll be surprised how many men don’t invest in their daily appearance.

Secondly, factors such as tonality and body language should be taken note of.

  • Body Language, Eye Contact and Tonality

You want to be going for neutrality and coming from a curious standpoint. You’ll also want to have assertive by soft eye contact. Neutral body language and an assertive tonality will demonstrate that you’re comfortable with starting this conversation, that you’re no threat, and you’re also confident with asserting yourself.

  • Understand Social Norms

When you’re approaching a stranger on the streets and hitting on her directly is something that’s out of the norm, and hence: should be recognized as out of the norm.

Going up to a girl and saying you find her cute is quite an unconventional behaviour. It’s not something that happens daily and should be recognized as that. Because I recognize this and I call it out in my own interactions, I rarely creep girls out. Most women I approach are willing to listen to me at least for 30 seconds.

How to Get Over Approach Anxiety

Even when you made a decision to go up to talk to that beautiful stranger, your stomach churns, your heart beats faster and you’re almost always left dumbfounded, unable to utter a single word, much less move your feet to go up to talk to her?

I’m no stranger this feeling called approach anxiety. Up to this day, I still get that crippling feeling of taking my feet off the floor, pointing it at her direction and walking up to her. I have failed to approach girls in shopping malls, nightclubs, parties and social events.

Approach Girls

Are You Going to Talk to Her?

However, compared to the average person, I’m a lot more competent at it.  So how you actually get over your approach anxiety?

Create an Environment of Inevitable Success

Firstly, you’ll need to create an environment of inevitable success. You need to use your surrounding for leverage. The only reason why I bothered to take action in my dating life back then because my ex-girlfriend broke my heart. I had so much leverage on me, that not taking action wasn’t an option.

In my entrepreneurial career, I feared doing something I hate, getting bossed around by someone that I didn’t respect and serving clients that didn’t enjoy serving. I hated all of that so much that publishing long-form guides, editing and blogging to promote myself as dating coach on a daily basis became effortless to me.

In your dating life, what kind of leverage can you use? For me, some of them include deleting all online dating applications. Today, I don’t use Tinder or any of the online dating applications. I don’t hang out with people I don’t like just so hopefully they can introduce me to their girlfriends. I don’t do any of that. I run this business alone. I do not have colleagues, friends of friends that ‘hopefully’ fall through the cracks so that I get to know them.

This is why I have leverage. I have no alternative and created an environment of inevitable success.

Technical Solution – Progressive Desensitization

You can work your way through your approach anxiety through the progressive desensitization technique. I use this technique on myself and multiple other clients.

Progressive desensitization is a psychologically researched technique that is used to help people overcome their anxieties in a step by step manner. Compare this to the flooding technique where most dating coaches force students to approach 20 hot girls in one night at a go. Firstly, it isn’t sustainable. Secondly, you’re not building a sustainable habit.

Okay, here’s an example on how to use progressive desensitization:

Step 1: Remove Headphones in Public and Being more Socially Connected

Firstly, you can remove your headphones when going about your day. I removed my headphones and was shocked at how much difference it made how connected I felt to the social world. You should try it. This forces you to be much more socially engaged with the outside world.

Step 2: Ask For Time and Directions from Strangers

If you’re crippled by approach anxiety, you can start off with total strangers and then work your way from guys, non-threatening girls and then attractive girls. You can also start off by asking for time or directions, moving up to compliments and then eventually the direct approach. You get the idea.

Step 3: Making Small Observations and Compliments

Small observations and compliments can be stacked on top of asking for time and directions from strangers. When you add a compliment: “that’s a nice shoe, you look great in it” in your conversations with random strangers, you’ll not only make their day, but it’ll put you in a better social mood when you get positive social feedback.

You’ll be surprised how much just stopping strangers to ask for time and directions will help in getting the social juices flowing.

The Minimum Viable Action

One tool I find helpful when I find myself stuck when approaching is called the minimum viable action. It’s the one action that you can do other than the direct approach itself. That can be approaching her for time and directions. This not only gets you comfortable stopping attractive girl, but it’ll also help you become more desensitized and get in a more social mood.

Blast Through Your Excuses

Through the years getting into this, I realized that success with women boils down to one key factor. That’s integrity. Not your kind of school integrity, but integrity to push through your social fears. It’s a personal badge of honour you wear to push through your fears.

When you’re pushing against your approach anxiety, you’re bound to fight against your own psychological defence system. They are called psychological defence mechanisms. Here are some common excuses you’ll tell yourself.

  • Avoidance and Procrastination

“I am going to start on this girls thing tomorrow. I’m just not feeling it today.”
“I am going to starting hit the clubs next week.”
“I don’t feel like it today.”

There was once I was practising to approach at the mall and tons of excuses and defences popped up. First I told myself I was tired and had to grab a meal first, then a sweet drink…

I didn’t do any approaches for the first half an hour. I spent the time, eating, drinking and waiting around. It was only when I started paying attention to the monologue in my head that was able to start calling myself out on the excuses that popped out.

Here’s the truth: There’s no perfect night and no perfect mood to approach. Just because something feels absolutely terrible in a certain moment does not mean that it is. It’s only when you get your butt off and start approaching that you feel much better. I can’t tell you the number of times I’ve felt horrible and not wanting to get out of the house and then feeling much better after stepping out.

  • Intellectualization

The self-help, dating advice industry is notorious for this. If you consume dating advice and watch videos without taking any action, you’re intellectualizing your problems. I used to do this a lot when I first start out where I would just read, read and read some more. Overloading myself with one theory after another. It’s also a false trap. That’s because reading and watching videos make you feel like you’re doing something. However, it does not.

  • Apathy

‘I genuinely don’t care and it doesn’t bother me.’

If you’re watching porn and telling yourself that you don’t give a fuck about your sex life, you’re running into apathy. You convince yourself that you don’t care about your dating life. I know for sure, I was there. Truth is, I do care about my dating life.  This bled over to my school, life and all other areas in my life. It’s something I’ve had to fight against for the last 3-4 years of my life. It’s a defence mechanism I run even up till today.

  • Helplessness and Surrender

‘I just suck at this.’
‘I’ll never get good at this’.

I found myself running into this defence mechanism sometimes. I get too anxious and then I surrender to the anxiety and just admit that: ‘I suck and have no courage.’

This is the opposite of apathy. Caring too much and acknowledging that you’re powerless to taking action against the anxiety.

  • Blame and Anger

This defence mechanism mostly comes in the form of generalizing and stereotyping chunks of the human population. When I first started out going out to approach girls I told myself this approach thing only works in Westernized cultures. That it’ll never work for Singaporean girls. Singaporean girls are too materialistic, socially retarded, bitchy and emotionally immature.

Your First 5 Minutes

You’ll be expected to lead and initiate 98% of the time, and I mean 98%. I’ve lost tens of interactions because I played it chill and laidback. It’s incongruent to the girl if you approached her and expect her to lead. She’ll be wondering what is up. You just approached and you’re playing in chill?

She’s not going to lead the conversation or add to the conversation. That’s because you’re approaching her in an unconventional manner and she’s going to be quite shy and reserved. You’re going have to make statements, ask questions, tease her, and laugh at yourself to put her at ease. You’re going to have to communicate to her within that 10 minutes that you’re an attractive individual that’s socially aware as well.

  • The Approach

The fundamental principles of old approaching girls in nights clubs or day time situations are similar. 1) You need to present yourself assertively and positively 2) you need to be willing to back off. If she’s taken aback, you need to be able to show that you’re willing to back off through your body language. Secondly, don’t touch her heavily when approaching, use hand signals or a light touch to stop her.

If you’re approaching groups, you should also talk to her friends, both male and female.

I recommend beginners to get comfortable with going direct. Going direct puts you out there and let your intentions get known. It’s also time effective method. It’s genuine and authentic for beginners, this is it can work for you. I personally am a huge fan of going direct, however, as you progress, going indirect can be more effective, less socially awkward for her, especially in a conservative culture like Singapore.

These days, I start off by saying “I know this is random”,  followed by: “I think you look interesting (indirect), and just wanted to say Hi”.

The majority of girls are going to figure out what you’re trying to do anyway. The indirect approach simply subtlety conveys: Hey, I’m officially invested in the prospect of getting to know you better.

She can also mostly tell if you approach her for any other reasons than being attracted to her. You should not approach girls to impress your friends, for ‘practice’, for numbers etc. I have approached girls that I am not genuinely attracted to, for ego reasons to impress my friends and it usually doesn’t work out.

Your motivation behind your behaviour is equally as important as the behaviour itself.

  • Questions and Statements

There’s nothing more boring than getting to know someone by asking a bunch of questions. If you’re only asking her questions after questions, you’re putting all the spotlight on her and you don’t get to share your identity to her. The easiest way to have a two-way conversation is to include ‘I’ and ‘you’ in your conversation.

Stop asking questions and turn them into both statements about her, and yourself. If you only ask monotonous questions, you’re severely limiting yourself. There’s no connection and no rough edges. Through the art of cold reading, you turn questions into statements. You can also find out about her occupation, her hobbies in a way that doesn’t come off as being an interviewer.

  • Tease Her about Something She’s Doing in the Moment

Teasing helps ease the interaction between you and her. Old friends tease each other all the time. You do it with your family, you do it with that childhood friend, most of all, you do it about your most embarrassing personality traits. It also adds a man to woman element to your interaction.

One of the easiest ways do it is to tease her about something is doing, about to do or wearing in the moment. If she says she’s an accountant, you can tease her that she probably lose money for the company rather than account it.

For Eg. I was at a beer pong party and she was telling me how good she was at beer pong. I told her that, that playing beer pong was probably her college major, insinuating that, that’s probably everything she knew about life.

  • Qualify

Lastly, you qualify by finding something unique about her lifestyle, job or occupation and appreciate something about her by saying: that’s really interesting, I’ve never met a girl…’

Imagine if someone took the effort to notice how you put in effort something you care a lot about, perhaps your business. Imagine if someone went on to say: ‘you know, I really like the details of your work, there must be a lot of effort and attention that goes into that, not everyone is willing to go through the pain of building a business’. How will you feel about that? You’ll feel amazing. That’s right! Now, flip that around and find something unique about her and appreciate her for that.

Note, you can’t fake it when you say something, you got to mean it. Take this as an opportunity to cultivate a genuine appreciation for others.

It can be as simple as:

‘You’re really friendly for someone that looks pretty young’ (I use it all the time in Singapore because girls here are usually shy and reserved)

‘You seem like a friendly and interesting person to talk to’.

Make Future Plans on the Spot 

Here’s the deal when attempting to get her number. Only ask for her number after a positive interaction and you can tell that she’s minimally interested. Secondly, get straight to the point by asking her out for coffee or drinks right then and there.

Through making future plans right there, you’ll solidify yourself as someone she’s potentially going to see again. You can also add in a little qualification before asking for her number. Let’s say you found out that she has quite an upbeat personality, you can say:

‘That’s awesome, you seem like a fun and adventurous person, let’s hang out and go bungee jumping together some day.’

Or, if you just find her pleasant to be around with. You can say:

‘You seem like a cool person to be around with, let’s party someday together. Do you have WhatsApp?’ 

Note: If she’s only willing to give you their Facebook, Instagram or Snapchat, then she probably isn’t attracted. I don’t buy that, I’ll just treat it as a rejection and move on.

Bench Mark: Staying in a Cold Interaction Longer than Half a Minute

The rule of thumb is this: IF you are able to hold a conversation and stay a cold social interaction for longer than a minute, you’re approaching correctly. If you are getting blown out interaction after interaction in less than 30 seconds, then you’re not approaching correctly.

You need to look at the basics: your body language, your dress sense, your vocal tonality and your intentions. Girls aren’t stupid, in fact, they are a lot more emotionally intuitive than men. If you are approaching her with the wrong intentions, she’ll figure out.

Note on Crazy Pick Up Moves

There are many pick up artist techniques popularized like spinning girls off the approach and outlandish behaviours from Youtube videos produced other dating advice companies. Here’s my verdict on them: they aren’t sustainable. I’m sure those instructors are good, however, they are only showing the tiny fraction of the interaction. They are also showing these flashy techniques for marketing purposes. It also rarely works when approaching girls in conservative Asian cultures like Singapore. Secondly, if you can’t even get a girl to stop and speaking to you for half a minute, then don’t even bother about all the other techniques.

There were times I ran around the club like a headless chicken approaching girls just for the sake of it. I was relying on ineffective dating theories and not approaching from a place of effectiveness. They are also socially uncalibrated behavior. Needless to say, I got rejected repeatedly.

Ultimately, you can’t really completely objectify or quanitfy social interactions. However, if you aren’t getting results then it’s time to put some metrics into action. How long are you staying in an interaction? Is she smiling at you? What does her body language say?

Results and Success

The majority of your approaches are not going to go anywhere. It’s the name of the game. There are just too many external circumstances that cannot be controlled. EG. She has a boyfriend, the last guy that approaches her on the streets freaked her out etc. The better you get, you’ll be able to point out the interactions that aren’t going to get anywhere and you’re going to spend a lot less time on time sinks.

If you want to get optimized results, you get good at the fundamentals: intentions, relaxed body language, eye contact and conversational skillsets. Lastly, remember that it’s your responsibility to approach her. It’s always your responsibility to move the interaction forward. It’s always your responsibility to spark an interesting interaction between you and her. Cause if you don’t, she’ll never do it for you, ever. 

Spead The Love

About the Author

Marcus Neo is an entrepreneur and coach. Enjoys writing about dating, relationship, business, and psychology. Introvert yet extrovert. Likes martial arts and music, but never got around to the latter.

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