That car jacking line was funny man lol
There's definitely ways not be creepy, but there isn't really a way to not be interested, which means you have to make yourself vulnerable, yelling at a woman from across the street, 'WHAT UP", with your boys isn't that, right? you have to expose that vulnerability, and the possibility of being rejected on some level. That's what's hard for many people. That's what confidence is. Like your story, she could have looked at you crazy and drove off.
People approach me, and I approach them, sometimes it's as simple as "hey I see you all the time, my name is _____", and the convo will flow. Timing and context is important to, like if someone seems stressed, busy, on the phone, I let that pass.