No, people almost never talk to me. I recently had a drunk guy harass me, but he wasn't talking coherently. And then I think he tried to run me over. (True story. Though I'm not sure he was the one driving.)
When my anxiety wasn't as bad, and I was much younger, I was like you. I spent hours every day in coffee shops, libraries, bookstores, and generally out walking the streets, surrounded by people. I did that for about 10 years. I've always been friendly, and smile at people (mostly to assure them that I Come In Peace) and I don't recall a single person ever approaching me for conversation (with certain exceptions*). The only people who said anything at all were the people running the checkout.
Those exceptions being: drunk people harassing me; panhandlers asking for change; and people trying to buy weed off me (I've never even bought it myself, but I guess I 'look' like someone who'd get stoned). Also: the one time the police questioned me because they thought I was a suspect in a crime.
Based on my experience, you will die of old age before someone will do the approaching for you. So I recommend you find a way to do it yourself.
The only thing better than money is more money.