I think you are meaning “confident that this will go your way” when it should be “confident that your mood and well-being are going to be fine no matter how it goes”.

The second one takes the anxiety out and let’s you respond to how things actually are, instead of comparing to some other story. Then you can see yourself, the situation, and the other person more clearly, which helps make experience more worthwhile in any event.

Of you’re bothering someone it’s not because you’re confident, it’s because you’re socially inept.

I say this as someone who was very socially inept for a long time, and today I’d say I’m just not as socially “ept” as some people I admire or as I’d like to be.

Socially “ept” people are first interested in others, not in their own ideas or goals first. Or at least they’re damn good at focusing on the needs of others first. I’ve worked for some people who are incredible at this. Some actually care about other people, others are good at giving people what they need, to get what they want, yet you still walk away feeling good. (That’s a very interesting experience).

(Is “ept” a word? I haven’t looked up the etymology of “inept” yet).

I think it’s been conflated with simply “having self-esteem”. So many guys (and a few women), are just so meek and weird about flirting or even just having casual conversations with the opposite sex. Like they see themselves as a social burden, but they just have to approach and give weird compliments anyway.

Like, you’ve seen sorta fugly people with attractive partners, right? Or two not-so attractive people dating? Someone had to make a move, and those people had self-esteem / confidence.

Confidence isn’t just reserved for the physically attractive. It’s ok to value other aspects of yourself and derive your self-worth from that.

If you’re bothering people who turned you down already, or you’re too unaware to notice, then that’s a different problem altogether. I’ve seen plenty of guys with zero confidence linger in a convo they thought was going somewhere.