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Alana: a-LAH-na (the lowercase a's are like schwas)
Alanna: Same as Alana, but maybe with more of a "catch" on the n sound. So it would be less like a-LAH-na and more like a-LAHN-na.
Alannah: I'd probably pronounce this like Alanna, but I could be convinced it's a-LANN-a (rhyming with Hannah).

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I don't know anyone with any of these names.

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1) Alana
2) Alanna
3) Alannah
(I think this is one of the names where simplicity is best!)

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I'd assume Alana

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I don't think it's dated or boring. It reminds me of those Tamora Pierce books where the main character was named Alanna.

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An Alana would be pretty, smart, imaginative, dreamer-type person, who gets along with people but is always willing to fight for herself and others, a bit reserved but never too shy to express her opinions when needed.
An Alanna would be similar, but maybe less of a dreamer and more outgoing.
Alana and Alanna would both have brown or red hair.
Alannah would be more prissy, less noble, less intelligent, and more superficial.