I have made it a goal of mine to be able to talk with ANYONE on the train on anything. No more being in my phone.

I can try to hold the conversation once it takes place, but I have trouble starting it.

My "method" is commenting on a special item of clothing but I would like to broaden myself to people without such easy "hooks" for conversation. I also usually talk with young people but I believe I should be able to talk to old people (but I don't know how to).

And don't say "just start talking" because blurting "so what do you do for a living" straight out is fucking awkward. I know that you need to ease up into small talk when not in a social setting (train, street etc) I just don't know how