Do you remember your 1st 1up experience? I do because it just happened!
In all seriousness, riding solo is one thing - someone else placing their life in your hands is obviously on a whole different level.
I spent a little over 2 1/2 years learning how to ride on the Honda Rebel I bought. I got my endorsement and the fundamentals down. I then bought my RT, and spent a month getting used to it myself - the weight, the balance, the additional power (I bought a low suspension model because I am somewhat vertically challenged.)
On Sunday, March 25th my wife joined me for the very first time on the RT. It was a little overcast and cool, and it was a short 20 minute "jaunt" through some back country roads.
Needless to say, I was nervous - but confident. Confident I had done the right thing in waiting until "middle-age" to learn how to ride. Confident I had done the right thing in buying a "starter" bike and going through the MSF to get my endorsement. Confident that even when I bought my Rebel, I kept my "eyes on the prize" (an RT!) and our long term goal to spend more time together and do some touring.
I know she was nervous as well, and righfully so. But she knew the steps I had taken to get us to that point, and knew I would never let her ride unless I felt like I was ready.
Afterwards, we had a great discussion outside beside the bike. How safe she felt, how the seating position felt, how was the wind, how was my balance, how well I could see with the RT mirrors, etc.
All in all, it was a great "ice-breaker" for both of us. Maybe not a great "ride tale", but just a reminder to us all that everytime we go through our pre-ride checklist - "Taking someone else's life in our hands" should be one of those items...