I remember once someone in chat tried to bet 100 rep with someone else about some silly thing. Something like, "I bet you 100 rep this you can't tell what animal is in this picture!"
At the time, it wasn't really feasible for the loser of the bet to pay up, so we probably had to beat him up instead. I can't really remember.
Now I realized that it is actually feasible nowadays, since you can award bounties to arbitrary answers on arbitrary questions. All that is required of losers is that they have the ability to post bounties, and of course, the necessary amount to pay up. Then they go find an answer by the user who won the bet, and post a bounty on its question. Once the bounty award cooldown expires, he awards it to an answer by the winner.
The system is not perfect yet. It is it hard to have an elaborate betting system with different odds and all that, because among other things, payoffs can only be given in fixed amounts.
At least this let us use up our own hard-earned imaginary Internet dollar points in a truly adult manner. It opens up a whole world of possibilities. It would make real mafias possible and maybe some day we can mount a protection racket scheme and collect payment from chat rooms. Would it be frowned upon if I became a bookie?