Most Helpful Girl
I did, but I started to get to know the guy right when he approached me. I don't think I would have dated him if he just came up to me asking for my number.
Most Helpful Guy
That's how I meet and date women. So the answer is yes, they will.
You will get rejected more often than not, but once you get used to that, it isn't a big deal--nothing more natural. You'd get rejected a bunch whether you're in a bar where it's "normal" (lol) to approach, or anywhere else, why should the street be any different?
Think through the things a woman would worry about when getting approached by a male stranger, then make it clear in your body language, approach, and tone of voice that you are a relaxed guy who isn't someone to be afraid of. Take rejection gracefully, don't over-pursue.
You'll have to experiment a bit for what works best for you, so adopt a testing mindset if you don't want to always get rejected. Try to learn what you're doing wrong with each approach (likely she just isn't interested, but always imagine you did something wrong so you can unearth a lesson).