
It’s easiest to approach someone in a group you’re already in like a club, class, etc. because there’s an expectation of social interaction. Next easiest place is a bar type place where people have to sit next to each other and so invite conversation that way. Random walk up’s are very hit or miss.
But I as a person am fairly standoffish until I know someone. I’ll be sweet and friendly until they try to move to “ask out on date” and then I’ll get awkward or uncomfortable because I don’t know them. Too many times my friendliness has been interpreted as flirting. Its not. I just pay attention when most people are talking to me unless they’ve already made me uncomfortable.