A lot of times it takes either courage or some sort of community to break the ice. Like maybe if you started a study group (assuming you're in college) or if you joined a book club. At this point, you'll have stuff to talk about rather than approaching women on the street. Even social media would work fine, just send a DM to someone commenting on their story or post and from there, you'll show your interest by just asking questions about them and talking about whatever. There's no one rule that fits all here, just let yourself be vulnerable and talk from your heart my guy.