A) So its not about courage. Its about logic. It takes some work to get logic to beat emotion but with practice you can. Took me about 3 weeks to psyche up to this tbh. Anyway, simple answer is Nothing Bad Will Happen If You Look Stupid. No matter how cringey you might be, you can always just walk away after. Most of the time other adults will be happy to pretend nothing ever happened too.
B) I work on a college campus so I'm there in the normal day to day of things. I have no idea how people meet women socially outside of school/work. I do go out drinking etc occasionally but never to hit on women. In fact I get hit ON way more than I hit on other people (mostly by thirsty gay dudes if we're being honest. Apparently I'm like the epitome of bear). That said, all three are girls I know from work and one of them could ruin me if she wanted (the first one). Eventually logic dictated it was worth the risk and eventually the rest of me agreed with logic.
when i look at things "logically" i typically come back to two thoughts:
1) everyone will laugh and ill be kept awake at night forever due to this memory 2) nobody would ever logically want to be with me anyway :(