I (27M) have been looking to build confidence to approach. I have confidence in day to day life (I’m in good shape, get told I’m attractive) but only in the last few years have been able to speak to women. I’m fine with women I know and over text but thought of approaching terrifies me.

Anyway, I ordered Uber eats to my door and started making decent conversation with the driver (probably mid 30’s woman, decently attractive) and as she was leaving I thought to ask for her number and couldn’t get the words out. So my question is: once you make the leap once does it suddenly become 10x easier the following times?