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I work in field sales and have to take clients out for a meal, on occasion. Had one that always picked extremely expensive restaurants ($40 and up per entree for lunch, final bill $80 per person). While my company does not frown on this, I felt this client was always taking advantage of the situation. I eventually just picked the restaurant in advance. He got the message.
I have a repeat customer that orders several items from me every year, each one requires specific size, colors and styles to be chosen. She emails me what she wants, I email her back and get the most bizarre replies.
It took me a year to figure out she's answering emails on her phone and not scrolling down to view the entire email. Now I send very short, one line emails.
This same person also complained about a very expensive non-returnable custom item that we sent in the style she agreed to and paid for, details on the invoice, but later on she said she had ordered a different style. Nope.
Then she tells me that she had a conversation with a co-worker and they decided they wanted a different style. She argued for weeks that we should replace at our expense, because they decided on a change. They just never told us. I guess she thinks we should have mental telepathy. She even sent me emails as proof they made the change, but they were to each other, not me, which was pretty hysterical.