[name]Rupert[/name] what do you think of when you hear it.
i like it.
The name [name]Rupert[/name] makes me think of…debonair actor [name]Rupert[/name] [name]Everett[/name], [name]Rupert[/name] the bear, stiff upper lips, [name]Eton[/name] schoolboys, cricket, English gentlemen, polo, strawberries and cream! 
[name]Rupert[/name] is a name of gentility and aristocratic quirkiness. I like it but it certainly won’t be everyone’s cup of tea!
It reminds me of the actor & I think it’s a little dated & pretentious in all honestly. Kids would likely shorten it, what would the nickname be? Rupe? Not a fan… It would make an amazing middle name though!
I love it! It sounds a bit too kingly for me to actually use as a FN, but I do think it’s so handsome. If [name]Samuel[/name] was still on my list, I would have done [name]Samuel[/name] [name]Edison[/name] [name]Rupert[/name], [name]Rupert[/name] as a slight nod to my grandmother (who was a [name]Ruth[/name]). I think it makes for a very cool MN.