Here’s a photo I took recently in SF. I tend to approach people by complimenting their outfit, look or a detail (hair, a jacket, sunglasses) and then ask if they’d be into a portrait. They usually says yes, but if they decline, I don’t take it personally. I then own the scene. You have to make sure you have the light you want. That you’re analyzing your frame.
https://preview.redd.it/4g3uducn5fwb1.jpeg?width=3277&format=pjpg&auto=webp&s=284833b86940f0f5d77f6c7458696d0801b53216
This is another I took in SF as well. It can be intimidating to go up to people, but you have to engage. It’s the nature of shooting portraiture photography. And like any “muscle”, the more you use it, the better you get. You smile, you wink, you laugh a bit more. Jazz folks up. Ask their name. In the end, they’re just people.