Took a passenger on my bike for the first time today. Went well. Started by scooting around a residential area for awhile, then up 880 to the Original Pancake House, and then tried to do the Calaveras Boulevard ride -- didn't turn somewhere I should have and went on a ride that was much prettier and ended right back up in Milpitas, which was far more convenient. So it went great :-) The road was named Felten or Felter or something, I forget. Nice views of Milpitas most of the way. A little sandy, but not enough to be a real problem.
So now I've done that. It's a little odd, but not that hard. So I can offer to do so more reasonably. Yay!