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Endearingly dorky is a good description. I immediately thought of a bumbling but well-meaning father-in-law. (Not mine, mine is a Roger.) Kind and a bit awkward, rambles quite a bit.

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Cool way to include Ward. Although I think Howie is sweet as a nickname.

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My favourites of your list:
Howard Laurence
Howard Jacob

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Also decent:
Howard William
Howard Christian

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Somewhat ridiculous:
Howard Rex
Howard Horatio
:)

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My personal favourites:
Howard Avery
Howard Everett
Howard Montgomery!!
Howard Roman
Howard Tennyson
Howard Sullivan
Howard Emery
Howard Mackenzie
Howard Josias
Howard Bram

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Three boys nappin', one mama namenerdin'
To peruse my top 100ish names: http://www.behindthename.com/pnl/82589

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"My Inner Birthing Mother Paddles a Canoe" and other non-name musings
found on my blog: http://jodifriesen.blogspot.ca/2014/07/paddle-power.html