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I think Rory is a great name for a boy, particularly because it's a masculine name to begin with. I agree; it's cool and spunky without being childish. Rory and Hugh are both great names, but together they do sound a bit abrupt. Maybe something longer would be nice. Here are a few suggestions:

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Rory Edmund
Rory Nicholas
Rory Willem
Rory Graham
Rory Frederick
Rory Lysander
Rory Francis
Rory Alasdair
Rory August or Augustin
Rory Malcolm
Rory Kenneth
Rory Leopold
Rory Eugene
Rory Douglas
Rory Adrian
Rory Jeremiah
Rory Christopher
Rory Leander
Rory Matthias
Rory Clarence
Rory Julian
Rory Tobias