Step 1.

You are not to go to any bars or clubs for the next month. At all. You may go to pubs with your friends, but no “sarging.” No bars. Nothing.

What you will do is make changes daily. Here’s how.

Step 2.

For the next month, you will take a 30-minute walk every day. Pick a neighborhood that’s easy to get to from home or work, and go there at about the same time every day. Ideally pick a place you can walk right after work. It can be a street with shops, or a park. But it must be a place where people are about.

When you are on your walk, you nod to yourself and keep repeating under your breath “I’m going to look silly but i’m going to have fun.” Just do it.

Now comes the crucial part. When you walk past a woman, ANY woman, smile, look up at her and say “Hello.” That’s it. Just greet her. She does not have to say anything back. These are the simple steps to get you out of your head.

You have that goal. Now the next thing to look for is a woman, any woman, who is not walking. Do the same thing. Walk up and say “Hello.” Wait until she says “Hello” back, then when she does, introduce yourself. She will then tell you her name, and then you immediately tell her how you take a walk every day and have conversations with friendly-looking people because you’re quite shy, and are learning how to just enjoy small talk and getting to know people.

Do NOT run any routines or anything else. Just have a conversation about how you have trouble having conversations. I want you to be totally honest and sincere. And if she joins the conversation, that’s great. Keep talking. If she has something to do that prevents her from talking, that’s fine as well. Wish her a good day and move on.

In short:

When walking past people, smile and say “Hello” to one person. It does NOT matter if they say Hello back or even look up.
The first woman you see on your walk, stop and greet her with a smile and “Hello.” Then introduce yourself politely and ask her name. When she tells you her name, tell her you like to walk every day and have conversations with friendly-looking people because you are quite shy, and learning how to be social and enjoy small talk.
Once you say that, you are free to go. You do not need to say anything else. But you are also free to stay and talk.
No matter what else happens, make sure you walk for the full 30 minutes.
Get home and keep a checklist of the things you did. One check for walking for 30 minutes. One check for everyone you greeted with a hello. One check for every woman you stopped and chatted with.
When you see you have three checks, celebrate. Go to your favorite pub and watch the game with your buds. Order your favorite food. Give yourself a high-five. Whatever. But make sure you celebrate doing it.
Give me 30 days of this, and you will have a better life. I give you my word.