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Dexter

Dexter definitely. It has a cool, jazz leader, 1920’s vibe to me!

I prefer Howard because it's softer.

I like both but they are completely different. Howard sounds more like a mundane professional nerd that you grew up with. Dexter sounds like a mad scientist cartoon nerd. (The CN show ''Dexter's Laboratory''). And then, there's the television series just titled ''Dexter''.

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I'm choosing Howard because I take it more seriously, while simultaneously am less afraid of it. However, dexter is *cooler*.

Howard at all costs.

Dexter

Hm. They're both about equally likely to seem unfortunate or cool depending on the bearer.
I don't have a strong preference. I think if I were naming a son I'd go with Dexter, but I'd have to call him Dex, not Dexter because saying the -xt- sound doesn't appeal to me. Howard is not a bad name, but I feel like it's still stodgy and square, like Walter or Reginald or Herbert.

Howard hands down. Strangely though I do work with someone who has one of these as his first name and one as his last name.