July 25, 2016


Approaching - The First Frustration

This article is lesson 1 of 6 in our Six Frustrations series.

Approaching Women - The First Frustration

The worst thing about approach anxiety is the regret.

You’re out with friends, and you see someone you like. Maybe it’s her glasses or her smile or her hair, but you think, “she’s my type, I bet we would get along.” She looks at you, and smiles. Maybe she sees it too.

She wants you to talk to her.

But you don’t know what to say.

So you wait. And wait. And then you’ve waited to long and she’s gone.

Of all sad words of tongue or pen, the saddest are these, ‘It might have been’.

– J.G. Whittier

Of all the frustrations that men shared with us in our survey, this was by far the biggest.

They wrote in saying:

My mind goes blank once I decide to talk to a woman

I just never know what to say, so I hesitate and get all self-conscious

I feel like when I like a woman, I automatically assume she’s not interested in talking to me or she must be busy. So I never approach

When we did our survey, we expected breaking the ice and approach anxiety to be at the top of the list. But we had no idea how much it affected the lives of the guys who suffered from it.

The rest of this lesson is going to be about approach anxiety, and how to start a conversation. But it’s also about killing regret and fear, and living life to the fullest.



Approach Anxiety

The best advice I’ve ever heard about approach anxiety is something I overheard Dave Vox tell his students at a bootcamp a while back.

“You can’t solve your approach anxiety by thinking about your approach anxiety”.

It’s simple, but powerfully true.

Everyone gets approach anxiety at some point. We all feel a bit nervous starting a conversation with someone we like. It’s natural.

But some guys see approach anxiety as a problem and they try to think of a solution to it.

Other guys accept it and act anyways (even though they feel a bit uncomfortable).

The guys who try to think of a solution to approach anxiety wind up getting caught up in their own thoughts. Instead of finding an answer, they only focus their own mind on the fact that they are anxious. So their anxiety just gets worse.

Intellectual types are the worst for this – after all, they’re used to reasoning their way through their problems. But you can’t use reason to change a mind-state that wasn’t caused by reason in the first place. To put it another way, an irrational fear isn’t going to respond to a rational argument.

So stop trying.

You need to short-circuit your brain.

Forget about reason. Forget about your neo-cortex and your inner monologue, your higher cognitive functions, your years of education and training. Forget about the teachers who told you to sit still and think carefully before speaking. Forget your cowardly amygdala ringing like a warning bell inside your head.

The change you are looking for won’t come from your mind. It will come from your body. It will come from taking ACTION.

So you warm up. Stand tall. Hit the dance floor a bit. Smile. Make eye contact. Give someone (even a friend) a high five. Ask someone a simple question. Give someone a casual compliment. Sing along with the music. Distract yourself.

You know what’s a good way to distract yourself from your inner monologue?

Chatting up a girl.

So, what do I say?

Guys always ask me what to say. They’re obsessed with that opening line, as if the right opening line will make everything easy for them.

I’ll share a secret.

The opening line doesn’t matter.

You can open with almost anything.

The second thing you say, on the other hand, can be important, and the third.

But do NOT get fixated on that first line. It doesn’t matter. Just approach.

So open with “Hey, I’m Chris”, “You guys look like fun”, “You are absolutely gorgeous, I had to come over and say hi”.

All these work. And when you’re in the right mental state, they work really well.

I’ll share another secret.

My first conversation of the night always sucks. I say “Hi, I’m Chris”, I ask a few boring questions and fumble over my words. Then I awkwardly excuse myself.

Every single night I go out. And I have to do this in front of students.

The good news is that my second and third conversations work WAY better. That’s because I’ve pushed though my approach anxiety and told my amygdala who’s boss. My mind gets clearer, and more confident. My mojo returns.

But the longer I push off that first, awkward set, the worse it gets for me.

So, just do it, now.

Say hi, introduce yourself. Tell her you like her glasses. Say something that is imperfect and don’t be afraid to screw it up a bit. There’s nothing embarrassing about being outgoing and friendly.

Your Homework This Week

Reading is pointless unless you take action, so I want to give you some homework for this week.

  1. Go out, somewhere social. Somewhere that is just a little bit outside your comfort zone. That might be a club, or a friend’s party.
  2. Don’t THINK about being social or having fun, if you must, focus on your body and moving in a way that is fun.
  3. Don’t THINK about what to say. Just say something. Do that at least three times.
  4. Feel yourself get into a social mood. Now try being a bit more clever with the things you say, but don’t over think it.

And remember, failure weighs ounces, but regret weighs tons.


-Chris Shepherd


P.S. There are five more lessons coming over the next few weeks, if you found this lesson useful, please tell your friends! Send them to the Three Question Survey to sign up, or share the Six Frustrations blog post with them so they can sign up themselves. Also, let me know what you thought of this week’s lesson!

Related Posts

Chris Shepherd
Chris Shepherd


Leave a comment

Comments will be approved before showing up.