Money is never involved, but I’m always saying to my brother, “I’ll bet you a million bucks that (insert the name of one of our relatives) will do or not do something.” We’ve had a few relatives that have made some wildly stupid decisions, or have done things that are totally out of character for them.
Example: Our young, barely-made-it-out-of-high-school female cousin hooked up with a total douche-bag and got pregnant. So I said to my brother, “I’ll bet you a million bucks that she ends up pregnant again.” She did, and we had to have a family intervention to get her away from this guy (who turned out to be an abuser) away from her.
Example: My junk food junkie male cousin who never ate much beyond funyons, donuts, doritos, carne asada burritos and McDonald’s hamburgers, went to college and then announced to us that he had become a vegetarian. (I’m the only vegetarian in our family, so at first I was excited for him) but I said to my brother, “I’ll bet you a million bucks that he doesn’t stay a vegetarian for long.” I suspect that he “became a vegetarian” because he had met a young lady who was a vegetarian and he was trying to impress her. He not only stopped being a vegetarian, he’s now the biggest consumer of junky junk food and cheap fatty meat products without any regards to quality.
Example: One branch of our family was moving to another city. This particular branch of the family is known for being huge, unorganized slobs (although they’re really nice and a lot of fun). They said that they were going to clean up their stuff and get rid of a bunch of stuff and neatly box up the rest of it before they moved. So I said to my brother, “I’ll bet you a million bucks that they don’t get rid of anything.” True to form, they didn’t even put anything into packing boxes and another cousin had to go over there and literally shovel their belongings into the back of a U-haul, because everything was loose and nothing had been sorted or thrown away.