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I prefer Lindsay. I've met so many female Ashleys. I don't think it even sounds all that feminine. I don't mind it as a male name, but for a girl, I'm tired of it. Growing up, there were usually at least two Ashleys in each of my classes.

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Meadow Lindsay works.

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I like Willow. Willow Ashley has a decent flow.

I'd pick Ashley over Lindsay. Ashley was more popular than Lindsay was, but it's also prettier than Lindsay. Meadow Lindsay sounds fine, but I don't like Willow Ashley simply because I don't like Willow.

Lindsay. I dunno, it just sounds more real. Ashley sounds more fluffy and bimboish to me. Lindsay is to Ashley as Shannon is to Kimberly. IMO.

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Meadow is better than Willow. Meadow Lindsay is ... meh.
Willow Ashley has too many trees in it IMO. Also, it has a "waash" sound in it.

I definately prefer Lindsay. I think as middle names either one would be considered different.

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I don't think either one sounds that great with the names you have picked out however.

For a girl, I prefer Lindsay. Ashley is still a boys name to me. It would be nice to see them used as a middle name.

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Meadow Lindsay is alright, but I would never use Meadow as a name - it's just too hippy for me.

Ashley, hands down. If we had another daughter today, or yesterday, or tomorrow, Ashley would be her name.

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I don't like Meadow or Willow at all. Even Ashley can't save them.

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I also never liked Lindsay, it always sounded congested and snotty.

I like Ashley better as a middle name! I'm actually surprised by how much I like it as a mn as opposed to a fn. I like Willow Ashley, and Ashley grounds the nature-esque name.

I'd pick Lindsay, simply because it has a prettier sound.

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I dislike both, and I dislike both Meadow and Willow, so it's hard for me to answer. Meadow Lindsay has a better flow, I guess.

You know, you're right that they are dated and would be unusual today. I say go for it!
I'd choose Lindsay, because I know and love one. Plus I happened to grow up with three Ashleys, neither of which I really liked. But both names have the same vibe otherwise.

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Meadow Lindsay is very nice. Willow Ashley is okay, but I don't like the Willow-Ash thing together, it's too tree-y. :)