Here’s my take: I’d start with a quick, genuine compliment—maybe “Cool backpack! Got a treasure map in there?”—to break the ice. Or lean into the moment, like joking at a slow café line ... Asking for a tip works too—“You seem like a pro; any hidden gems around here?” It’s chill and gets them talking. To get them talking is the most important thing. One thing you must understand is people like to talk, specially about themselves. If you manage to get someone say about their story with a place, life, friends, and such, you've earned some points with them because people like the others who listen to them.