For me it has to be Microsoft Money.
There's nothing particularly bad with the program itself but the only time I ever click on it is when I'm about to do my tax return - and that makes my heart sink.
Which program has the same effect on you?

Openoffice
Because it's even worse than MS Office at making good looking documents without making your brain explode.

You don't fancy reworking my year's worth of data, do you?Quickbooks!You can almost guarantee that the user has got carried away with all the easy functionality and forgotten all about basic accountancy principles so I'll have to rework a whole year's worth of data.
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You don't fancy reworking my year's worth of data, do you?
No. Thought not.

SPSS?The statistics software my Psychology department uses, guaranteed to ruin your day.

I can't believe no-one's said Excel yet.
I fucking hate Excel.