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I like it. It's not a personal favorite, but I have a positve reaction to it. I prefer Derek, because Derrick reminds me of oid derrick. If I were in your shoes, however, I would opt for the Derrick spelling in order to ensure the correct pronunciation.

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The Dereks I know range in age from mid-fifties to toddler, so I don't consider it tied to particular era. Whatever the age, I picture Derek/Derrick as handsome and confident, perhaps loud and a bit of a daredevil.