Getting gonorrhea from unprotected sex, and after you get rid of it, going back to the bath house to see if you can get something incurable this time.
A 400 pound person going on all McDonald's diet.
After the drunk British football hooligans have rioted and burned down the stadium, you rebuild the stadium and, this time, to make it better, you offer free al-you-can-drink beer.
A prostitute getting out of "the life' by switching from cash to credit cards.
Losing all your money with Bernie Madoff, then convincing the rest of your family to break him out of jail so they can invest all their money with him too.
After the earthquake rebuilding your house on the fault line, instead of just next to it.
Giving your local alchemist your life savings to turn lead into gold, and after the lead remains lead, robbing the bank to pay him to do it again.
Invading Afghanistan to get Osama bin Laden and Mullah Omar, then, after you fail, invading Iraq to get weapons of mass destruction that don't exist.
Putting poison in your food to teach the dog not to eat off the table, then forgetting what you did and eating it yourself.
After you get lung cancer, smoking again because the worst has already happened.
Knowingly doing 2001-2009 all over again, a few people get rich, no new jobs are created, and the whole economy collapses.
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This is a contest. It's open to everyone. The writer of the best comparison gets to live with the consequences of whatever our loony legislators and waffling president do.