Excuse me for having a short memory, but here's my two from the last week or so:
Painful for the player: Michelle taking the prizes and having the car right in Temptation (I guess that's not a full loss, and she got DQ'd, but still...). Oh, and the one time I see Triple Play (last Friday), the guy gets it wrong on the 3rd car - that always hurts.
Painful to watch: That one lady last week who took all the time in Bonkers to make ONE guess. ><
(*cough* first post yay!)