I'm your typical Midwesterner that ALWAYS enjoys small-talk, however I wouldn't ask about specific holiday plans, as I think it's self-centered to think that everybody celebrates the same holiday. I'd say something more generic, and if they divulge what holiday they celebrate, then I'll ask more specific questions.
When I worked in the housewares department at a department store, we were told we could use discretion whether to wish somebody "Happy Holidays" or something more specific. If somebody was buying Christmas decorations, I'd wish them Merry Christmas, because that's obviously what they celebrated. Otherwise, I would say "Happy Holidays" or "Happy New Year". It seemed to work well, and that way, I hope I didn't make anybody feel uncomfortable!
ETA: I'm a big fan of the "Can you believe that it's almost <<insert upcoming year here>>?" That way, it leads into what they're excited for. But again, I'm a Midwesterner. We'll talk to anybody, doncha know?
When I worked in the housewares department at a department store, we were told we could use discretion whether to wish somebody "Happy Holidays" or something more specific. If somebody was buying Christmas decorations, I'd wish them Merry Christmas, because that's obviously what they celebrated. Otherwise, I would say "Happy Holidays" or "Happy New Year". It seemed to work well, and that way, I hope I didn't make anybody feel uncomfortable!
ETA: I'm a big fan of the "Can you believe that it's almost <<insert upcoming year here>>?" That way, it leads into what they're excited for. But again, I'm a Midwesterner. We'll talk to anybody, doncha know?
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