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Theodore

Samuel!

Samuel / Sam

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Because I think Theo sounds like it's one of those vaguely childish, weak, soft names girls sigh over like Dash and Felix, and I think is a good nick for Theodora instead. And because Theodore has ODOR in it. The odor. No, the other door. I'd rather Theodoric nn Odo.
Sam seems like it would grow up better

Samuel, but I like both

Theodore

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I hate Samuel. It sounds slimy to me, like a snot-filled loogie.

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If it were a question of just Theo vs just Sam, though, I'd pick Sam.

Samuel, by a small margin.

I greatly dislike all Sam names for males or females. Theodore is a whole lot better!

Samuel but I like both

Samuel.

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:)

Its all fine and well to insist on a nickname, but it doesn't always work that way. They may want to go by Ted some day or their friends will call them that and they won't care either way. My rule is if I don't like all the nicknames, it either goes in the middle name slot or gets cast aside.
In that case, if you don't like the nicknames, I would go for Samuel.

Samuel

Samuel.

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Theodore is so dorky, Roosevelt notwithstanding. And with Theo as a nickname rather than Ted, the dorkiness factor increases tenfold. I've always loved Samuel anyway so I'd choose it over most names, even if they weren't dorky like Theodore.

Theodore

Theodore, but...

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I prefer Theodor. If I had a son right now that's what I would name him.
And I really like Samuel as well, especially with the nn Sam, but nothing beats Theo/Theodore.

Theodore

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I just like the sound and nickname option better.