Hats off to Ben for keeping himself out there and enjoying/playing tennis. Most players would not even play against a young Junior like that, just for fear of the stigma of losing (but still talk about how they would beat them). I watched this the other day and I really don't think Ben played as well as he normally does, but then I don't think the kid was going all out either.
In comparison, I watched Ben play Simon Serves ( a 4.0 ) and again you can see how Ben has been so steady in his rating.
I find it fascinating that (many? majority?) people actually fear losing. What's so bad about losing in recreation? Rec tennis level is literally artificially constructed which means your wins and loses are also artificially constructed.Losing to a junior is no big deal and moreover you can adopt a fatherly attitude and joke about it and give him some tip like hitting with more topspin.
What hurts is losing to Fat Bobs your age and older.
One time I invited a newly retired man to play in our group, maybe in a singles with some guy his age when there wasn't enough people for dubs. He adamantly refused singles saying he's worried if he loses, it'll be on record for life!