I have tried talking to people a bit, with mixed results.
Awhile back I was waiting to get a haircut and I see a middle-aged woman with these boots, that look like the kind motorcycle racers wear. I commented to her that I had seen those in Latin America but never here. She was a bit bemused, and not at all interested in talking about footwear with me- “Yeah they have them here too.”
I was in a coffee shop and a woman sitting near me had a pink lid on her cup. I asked “How come you get a special lid?” and she said it was hers, she brought it herself. Apparently if you are super environmental you can bring your own reusable lid. I joked a little about it, she was a little more friendly than the previous woman but again not real interested in talking.
I think it helps to be more humorous. In another coffee shop there was a young woman with a sort of a flat purse or portfolio bag, bright fuschia vinyl with other bright markings. I commented “Your bag is bright!” and she went on a bit about how her crazy mother got it for her. I was in a gas station behind a guy buying four or five snack cakes, and I said “I hope those aren’t all for you!” and he said he bought them for women at an office he visited, it made him popular.
Maybe the combination of comment- it doesn’t demand a response- and humorous- it makes people laugh or puts them in a good mood- is what gets a positive response. You have probably seen a person who talks a lot, and talks about things people aren’t interested in, and is kind of a nuisance. I can’t stand such people, so I don’t like to talk outside of necessity with random people, but maybe that’s my ethnic background as well as my conditioned shyness.
Neil Strauss wants you to talk to all kinds of people; Roosh says that’s kind of pointless, you should talk to women you’re attracted to. I think it’s probably good to warm up a bit with people in general, but it won’t change your basic personality.