Oh, he knows it's waaaay toooo big-he lookes like an ant sitting on it! He has ridden before, he just let his license lapse because he was travelling a lot for work and didn't have time for it (or a place to store a bike, for that matter). He used to deliver pizzas on a bike waaaaay back when.
I've also seen him ride a friend's Road King with no problems. I'm not condoning it, and he and said friend got an earful after I caught him. But I actually was pretty impressed-he was doing figure 8's on it. I could barely do them for the exam, and he whips them out in a much tighter space on that big ol' bike.
He actually reaallly likes the S40 (he rode it in the parking lot and up the ramp into the truck while I was inside signing paperwork). I asked if he enjoyed his "ride", he went on and on about it. I said "Good, 'cause that's the last ride you take on it without a license!"

He agreed. I think he was at the DMV when he called me earlier.
Now that I'm riding, I think he's been bitten by the bug again. I still want him to take the MSF course though.