Wednesday night at 5 Walnut is pretty ideal for this kind of thing. The wine bar setup makes it easy to settle in for a trio without committing your whole evening, and 8pm means you can still make it a school night. This spot keeps it low-key and approachable despite the wine focus, more about catching live music most nights of the week than posturing over your pour. The window bar seats fill up quick, but the whole room stays relaxed whether you're nursing a $7 glass or grabbing a cheese board from the connected shop next door.