I want to become a very social guy who is not afraid to say hi to anyone and so Im wondeing how to open particular sets.

One for instance is a HB (your age) who is with her mom? is this possible?

A woman older than you with a baby or a kid?
This one I am not intrested in gaming. I want to be able to converse with anybody anywhere and i seem to have a big mental block when it comes to approaching women with kids. I can eaisly say hi to a dude with a kid but with a woman i have a fear as coming of as a pedophile or something. Could i make a comment about the baby or is it taboo?

A groupe of dudes?
This one i obviously don't want to game either, But there are certain situations i felt that by eaisly befriending them it could DHV me to a girl nearby.
Example: In a long line at a fastfood joint. HB at the cash register and group of dudes in line behind me.

I also feel i approach women better if i opened a complete stranger (be it a girl old person, whatever) a little while earlier.