They way to get confidence in making decisions it to make successful smaller ones and build up to bigger ones. So this should start at a very young age 2 or 3. Unfortunately our school system is not set up for this.
Also there are lots of people with lots of different hashkafos. So a girl from BY x can vary greatly. By chassidish where you both follow the same rebbe things are a but easier on that front. Also it could be more is known about the families.
In an ideal world less dating is better. However given the current state of affairs some people need more time. Others may need a push. This is not something to be taken lightly and each case is different.