...get an actual sized tattoo of Justin Bieber's head across your back? You can't get it removed or you lose the money
...work at a glory hole in a sex club that opened up a block away from your home? There's a damn good chance you'll end up giving oral to someone you know. There's mirrors arranged in a way that you can see who they are but they can't see you, and you have to satisfy everyone who puts their junk through the hole. No exceptions. If you're not into guys, then imagine it's some reverse glory hole where girls put their bits against a hole and get orally pleasured
...join the Westboro Baptists in a protest in front of the most popular area in your city? You HAVE to carry a GOD HATES FAG sign, and nothing you wear or carry can make it seem like it was ironic or that you were mocking the WBC. From all appearances, you'll look like one of them. For one whole day. $10,000,000 for a day of shame
...gain 100lbs and keep it for 6 months? You'll be given an enormous check a half a year later
...bang your best friend's significant other, and have your friend find you in bed together? You can't tell your friend in advance about the money. You can tell him/her after you're discovered though and offer your friend some, but will it repair the friendship?
Edit: the glory hole work would just be for one night only