People typically give these sorts of responses when either (a) they are tired or (b) they can sense that you aren’t actually interested in them.
You should understand that a and b are interrelated, as almost no one is ever too tired to express how they are feeling to someone they trust.
The trick here is not to keep asking questions, but to empathize:
“How’s work treating you?”
It’s work.
^ this “neutral” response is actually a polite negative.
“Yeah, tell me about it - my job’s boring as shit. At least it’s almost lunch time…”
Note that this doesn’t always work, and the person may just keep giving “blah” responses. That’s fine. You tried to connect. You tried to be interested. Accept their non-interest and try again with the next person. You will get better at being interested and empathizing with practice, and your increased care for others will become more apparent to others, generating better responses.



That’s a reasonable problem to have, but I think it is more created by your limiting beliefs than anything else.
Beginning or end of the day? During lunch? Even if you shoot the shit with just one person every day, that’s one more than you seem to be doing right now.
This is a symptom of being chronically online. Older people talk to younger people all the time. Hell, older people date younger people all the time. People like to talk to people, and if there are people around, its not weird to talk to them regardless of their age. As someone approaching my mid-thirties, one of my favorite ways to talk to college-aged kids is to lean into our age difference and just be like “so what are you kids these days all into?” And if you are worried about being a creep, you can lean into that, too “Hey, I hope I’m not just being a total creep right now, but I was kinda bored and wanted to see what you kids are up to.”
Finally, you can make small talk with literally anyone who comes into your proximity during the day. People waiting for the bus with you, people just chillin in the park, grocery store checkout clerks. For example, say you are checking out at the grocery store.
“Hey, how’s it going?”
^ this is the stock response that is just acknowledging you exist. Follow up with something that indicates that you actually give a shit.
“Day going good so far?”
etc