Or we would see he is human.

Of couse it is about knowing when to share things. The more personal things are for people you already have some kind of connection or relationship. The more common insecurities like "I've been to many terrible first dates" might be a bonding experience. Specially in dating apps.

The man who act as if they were confident all the time can give the impresion of being vain or fake. Because everyone has insecurities.

So there are tastes for everyone.