I feel like I should bet crazy amounts in a game of poker with friends
Get serious. Why would you choose to bet so much money?
Because it's fun, and it's really only $100.
If you want to gamble, you should only gamble as much as you are willing to lose. It is foolish to gamble large amounts of money, so think carefully about how much you will end up betting.
I think I'll win. I had this feeling before and I won every time.
Money is hard earned and in your case you could be wrong one day. Be careful you don't end up being a gamble-a-holic, that is something you should work on too.