Maybe a stupid question, but, if you view another rider (during an activity) the orange thumbs up appears next to the name. Is this a personal “Ride On” being awarded?
No. The orange thumbs up is a button. If you click on it, it awards a “ride on.”
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You would need to click on the orange thumbs up to give the rider a Ride On!.
I generally tend to give Ride Ons from the companion app, the little white circle saves a lot of messing around 
But yup, when watching a friend or someone else riding, the orange thumbs up is a simple way to do it.
Thanks for the clarification.