Funny - I don't count Nutcracker tickets as a Christmas expense. It is part of culture and entertainment for us that happens to fall at Christmas, to me.
The only way I could see us spending that kind of money would be taking a fancy trip for a week or so - skiing, perhaps - and buying new clothes and gear for it, eating at restaurants the whole time, shopping strictly by catalog and having things shipped, etc etc.
If I had $5000 to spend on something like that and wouldn't even miss it, it'd be a fun trip.
