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Even though I know you would be pronouncing Caroline with the -line ending, I still think its ending is too close to Marilyn. I really love the name Caroline, not only because it's my name but because it isn't too common and it's classic. I really love Josephine too though, and I think I might like it more because it's more unusual. Where I'm from I hear Caroline a lot, but I'm in the southern US where Caroline is a staple traditional girls name. Since you're in Canada I guess you shouldn't be concerned with popularity because neither name is popular... in which case I'd still go with Josephine.

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I don't get people saying Caroline is trendy though... I think it's the opposite of trendy, it's like Jane and Mary but way less popular.