I've arranged a few. Leant on by directors to arrange a do "to encourage team spirit".
I quite like socialising with colleagues and I'm good at organising, but Christ, Christmas dos are a nightmare! I think the type where people pay for themselves are the worst.
Yes to the people from different offices swearing blind they want to come and will 'settle up with you on the night' for the deposit then don't show. I resent having to chase them for the money afterwards, and it is always the highest paid people who think that their deposit doesn't matter and that they are too busy and important to transfer £20 to my account!
When it's booked you always get some awkward git, the day before, announcing that they are suddenly dairy or glucose intolerant etc., and will I just ring the venue and ask them to make a special dish for them? Or, ditto, demanding to be given assurance the day before that the kitchen is entirely nut free. If it's that important, why not bloody mention it when you signed up for the event, two months ago?
Yes to the whinging. I arranged one do with a buffet, one free drink per head and dancing. Free to the participants, the company having decided to put their hands in their pockets that year. You would not believe the whinging. One woman came over and demanded to know how much the event had cost. I caved in and told her for a quiet life. She said, "well, it feels cheap and I'll be checking how much money you've had out of [our employer]". As if I'd stolen some of the money! (She was later fired when the auditors discovered that she'd stealing from the company for years to put her son through private school.)
At bill payment time, I usually gently suggest that people add a bit of a tip. Loads don't. I usually end up doing the adding up (accountant), and loads of people come up to me with a handful of coins, including many coppers, saying, "my main course was £9.95, here it is, got to get back" then scarper. Neglecting to pay for their share of the sodding garlic bread, wine, etc. I end up adding £20 of my own money for a tip, because otherwise I'd be ashamed to face the poor restaurant staff!