By simple, I mean the cliched small talk questions that people on the internet seem to have a lot of contempt for. Had a great conversation with a lady yesterday that stemmed off of asking about the weather. Mentioned my work, she had a son in the same area, I asked her how many kids she had, how she met her husband, etc. Ended up talking about her cousin with a law degree who can’t find work here after immigrating. People have so much contempt for the simple questions, but they’re cliches because they work. You just have to listen and latch on to the things they mention.

Edit: Lets say a simple question is one where 100% of people have an opinion on it, 90% of that opinion is guaranteed to align with yours, and the remaining 10% won’t be a dealbreaker. Weather, families, sports, etc.

A detail somewhat overlooked by the previous commentor is that the simple questions about their life are much more effective when asked with genuine interest in learning about the other human being.

If one finds music interesting, perhaps asking the individual if they enjoy the sort that is playing, which opens up potential follow-up questions that's you may then use in the secret plan to learn more about this human being, their preferences, and whether further interactions might be mutually appreciated.