This is a bit after the fact, but I rode with my son for the first time last Saturday. It was a Mom, Dad and Son adventure.
This was Nick's first ride outside of the state park. He wasn't overly intimidated by the traffic. Just a healthy level of caution.
Dave and Nick are much faster than me. They did some double-backs, took some side roads and waited for me here and there.
His ride was around 22 miles. His rear is fine now but his shoes are too small. He has been using his off-road shoes and pedals. The shoes are less than six months old!

The guys took a trip to the LBS on Monday to remedy the problem. He purchased a set of Speed Play Zeros and ordered a pair of 49cm shoes. Choices are slim in this size. Cheap and expensive seem to be the only options. The mid-range shoes only seem to go to 48 and that is the size he is currently trying to wear. We went cheap this time but know that our next purchase may have to be on the high end.
We had the same problem with figure skates. Girls can incrementally go up as they improve but they skip multiple levels for mens skates and you have to make huge jumps in price.

They also purchased a pink Strada Wireless. I cleared the data on my black Strada and traded it to Nick for the pink one. The only pink accessories I can think of adding to my bike now are handle bar tape, hood covers and valve caps. I think I will pass on the hood covers. Dirty pink is not attractive. (I know there are some who would say pink is never attractive)

Nick is still not riding much. It is driving him crazy. He is rowing 5 to 6 days a week to help his brother get ready for nationals. He rows in a quad to give Drew's double some competition. The workouts have been more difficult than during the regular season. His hands are hamburger. The double seems to be doing quite well. The quad gets a head start and the double over takes it in short order. The quad is a bit of a motley crew as it is filled with whoever shows up. One day they were only a triple!

Thanks to all of the people who have left comments. Nick gets a kick out of reading them.