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Hmm, I think it is cooler than Oswald, but clumsier than Oscar (in terms of Os- names). I think it would take a certain type of person to make it work. The nicknames Oz or Ozzy make it hip, and Bert or Bertie is so sweet.

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I feel like it needs a quirky but posh British name to go with it:

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Osbert Karl / Osbert Carl
Osbert John
Osbert Rex
Osbert Alec
Osbert Archie
Osbert Desmond
Osbert Edmund
Osbert Felix
Osbert Guy
Osbert Hugh