Yes, even playing one I have never played before.
The first time I played and got into the bonus round on the Texas Tee pinball I cleared all 3 levels. The 2nd time didn't go so well on the 3rd level.
I would be willing to bet on myself VS random people on random pinball machines. I wouldn't want to hang around arcades asking people if they want to bet 1k on a pinball game, because I have to assume that most anyone willing to take you up on that offer would probably be fairly good at pinball.
I would be willing to bet on myself VS random people on chess, poker and pool as well. And no, thats not an open invitation to wager on any of them games vs members. Most people are only going to play you for money if they know they are fairly good at somthing.