Nice write up. I think it’s one thing to know what kind of person you are while it’s another to know the variables.

The girl situation is interesting because sometimes that pessimism helps in the sense that when you say “she’d most likely say no” it reduces your expectations and at the end of the day, it can work in your favour. I am not like that, I’m usually over optimistic about things like this which sometimes blows back on my face.

Finding the right balance might be the secret but like you said and I agree, don’t let me pessimism stop you from trying.