In short, I have trouble approaching with intent.

I used to have approach anxiety for just going up to strangers and asking for the time or directions. I tried gradual desensitization and it worked till when I tried to show intent.

I think I have some sort of mental block when it comes to initiating a man to woman conversation. I grew up in a very conservative Christian family where showing intent to the opposite sex was considered as a taboo.

I can overcome the fear of going up and talking to strangers, that's not a problem. But I think the root issue with me is showing intent

Yesterday I was talking to a female friend and we started to talk about relationships in general and I just lost all the knowledge I have about Game. It was going well up unto that point. Light-teasing (not flirty) and all. I just cracked.

I can show intent through text though. I have done it a few times. But when I have to do it face to face, I chicken out. How do I get over this?

TL;DR - Tried everything to get over approaching with intent. Trouble holding a man-to-woman conversation. Solutions?