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- When you approach, you must lead.
When you approach, you must lead.
Common pitfalls in approaching strangers
Hey!👋 Craig here—
I teach shy people how to approach strangers.
Some of of the most common sticking points I’ve been seeing with my clients lately are:
They get stuck in awkward silence after they’ve delivered their openers.
They don’t connect well because they’re directionless in the conversation.
The person they approached loses interest because they are having to carry the conversation with the stranger who started the whole thing.
All these problems arise from the same issue- NOT LEADING in the conversation.
If you’re approaching someone, you are initiating. You’re starting…
YOU ARE THE PERSON THEY LOOK TO FOR GUIDANCE.
They’re not looking to be interrogated.
They’re not interested in putting in all the effort to make a connection with the stranger who supposedly wanted to talk with them.
If you approach, you must lead.
How do you lead?
Start sharing.
Bring up things that you want to talk about.
Qualify— meaning, you should be trying to figure out if this person fits what you want in a new friend or partner.
This means that you should be guiding the conversation to where YOU want it to go.
If you want to connect with someone by leading, here’s 3 simple rules:
Share yourself before expecting others to share with you.
You can learn this skill easily at my free Sunday Zoom classes or from my threading videos on TikTok
Know WHAT KIND OF CONVERSATION you want to have.
What do you want to talk about?
HOW do you want to talk to them? Hint: Treat them like you would treat a really good friend.
Know what you’re looking for.
Knowing what kind of connection you want to make will help you to lead the conversation to those kinds of connections.
Of course these rules need to be put into practice before you start having a 180 on your conversations…
but starting to implement them now will have ripple effects in the conversations you have 3 months from now.
So go practice.
Start one conversation this week where you deliberately take responsibility for leading it.
Share something before asking a question.
Bring up something you actually want to talk about.
And pay attention to whether you actually like the person you're talking to — rather than worrying the whole time about whether they like you.
AND I WANT TO HEAR FROM YOU
Since this past spring, I've been doing a lot more teaching, coaching, and experimenting, and I want to better understand what you're working on socially.
What's difficult right now?
What are you trying to get better at?
What would actually be useful for me to teach?
I made a quick questionnaire. It should only take about 2 minutes:
WANT TO WORK ON IT WITH ME?
I'm also opening up some 1-hour private coaching consultations for $60.
Bring me the actual situation you're dealing with — approaching, conversation, dating, making friends, building a social circle, whatever.
We'll figure out what's getting in the way and spend the hour actually working on it.
Otherwise, try the three rules above.
And let me know what happens.
— Craig
Craig’s Media Curation
Here are some videos I want to share!
Here’s an example of the threading skill being drilled. If you practice this, it’ll be very easy to lead your conversations and never be at a loss for words.
Upcoming Events 📆
Trainings, Streams, & Social Events that I want to share with you.
Live Online Events
FREE 45-minute social skills workshops
Every Sunday, 2:30pm PT / 5:30pm ET
Can We Talk? [LIVE SHOW]

TikTok Live Show where dating/social coaches Craig & Madara answer questions about dating, social dynamics, and whether or not they hooked up.
Thanks for reading—I hope to hear from you soon.
Cheers!