I noticed a lot of people spend their whole day alone. Especially after C19. At work. Or at home. Talking to the same people day in and day out. And this is where all this approach anxiety stuff comes from right now. I noticed I too was struggling and needed to be more outgoing. Despite being in a relationship, I still try and talk to as many strangers as possible on the street, just to keep my brain going. (Though no longer women in a flirty way, I have written below what I used to do when I was single).

One technique I use to overcome this is I just ask strangers for directions in the middle of the city. Start with everyone, to warm yourself up. The old man. The business person. The grandma. The mom. The cyclist. The dude having a cigarette. The person waiting for a bus.

Once you are warmed up, then start to talk to people that would normally ‘intimidate’ you. (This is where most guys struggle). They see a beautiful woman and don’t know what to say. I mean the girls who you would never normally approach. This whole thing is for boosting confidence. Here is how simple it can be;

Ask them this question after approaching them. Relax your posture and make eye contact; “Excuse me, Is there a Starbucks on this block?”. If they say yes it is down ‘that street over there’. start to elaborate a bit and practice your on the spot thinking. “That’s great, have you tried their winter menu yet? What’s your go to?”. She will most likely give a simple answer. Even if it is just “oh, I don’t drink coffee” or “I’m a latte drinker”. At that point you either chose to leave the conversation there. (You are warmed up and can choose to move onto someone new.)“Thanks so much, you have a good day”. Or you can be more spontaneous; “Lattes are my favourite!” Back to the directions say “I’m not sure where that is? If you walk me to it, I’ll get you a takeout of XYZ?” You then get a yes or no answer very quickly ion the spot or a “sorry I’m busy”. Which is fine. Your only goal is to talk to people on this ‘assignment’. Any other progress you make is a bonus.

If she says yes, then follow up and go on as normal. If no then just leave it and say “I understand and appreciate your help. I wish you a good day”. At this point you move on and look for a new person to interact with.

If she does end up coming with you, be as open as possible. Tell her you are a tourist or make something up.

As for the coffee, opt for takeout cups. This gives her the freedoms to move around and does not trap her into sitting down with you.

After this and a chat you can then ask for a number and it shows you are not going straight in for a number. But also let’s her know your personality type.

I think conversation is a beautiful thing.