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+ If you heard the name KAY-lee, how would you spell it?
Kayley, probably. That would be my preferred spelling, it's pretty obvious from that how it's pronounced and it doesn't look overly trendy. I've also seen Kayleigh and Kaylee.

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+ If you heard the name KATE-lyn, how would you spell it?
Caitlin, or Katelyn. Caitlin would probably be my preferred spelling, even though I know it's supposed to be pronounced kaht-leen.

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+ If you heard the name HAY-lee how would you spell it?
Hayley. I prefer the spelling Haille, but it's definitely not as intuitive to pronounce as Hayley.

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+ If you heard the name KAY-lyn how would you spell it?
Probably Kaylin, but maybe Kaylyn or Kailin or Kailyn. Kaylin would be my prefrred spelling, for similar reasons to Kayley.

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HALEY - HAY-lee or HAL-lee? HAY-lee. Coz there's no double 'l'.

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KALEY - KAY-lee or KAL-lee? KAY-lee. Again with the double 'l', and because of Kaley Cuoco.

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KATLYN, KATLYNN - KATE-lyn or KAT-lyn? KAT-lyn, definitely. The 'a' in the first syllable is short unless there's an 'e' after the 't'. That's just English phonological rules.

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How do you pronounce CATELINE? Rhymes with 'Dateline'.

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How do you pronounce Caitlin? Caitlin I would pronounce KATE-lyn unless I was told differently, just because I know most people use that spelling with that pronunciation.

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What about Caitlín? kaht-LEEN. Which I think is the proper Irish pronunciation. My reasoning being that if they've popped the fada in there they're probably more interested in the correct pronunciation.

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Do you think it's wrong to pronounce Caitlin as KATE-lyn? I think that it's so widespread that it's not 'wrong' anymore. Like how words change their meaning and pronunciation over time, I think KATE-lyn has joined the ranks of 'correct ways to pronounce Caitlin' (outside of Ireland, anyway).

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What about Caitlín? No. That fada means something in terms of pronunciation, and ignoring it is kind of like putting the umlaut over the final 'e' in Zoe, then pronouncing the name as 'zo'.

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What do you think of Cateline? It's counterintuitive as a spelling for KATE-lyn, and is not particularly attractive overall.

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What do you think of HAY-lee, KATE-lyn, KAY-lee and KAY-lyn? Do you see them as trashy, trendy, cute, strong what is your first impression? I find them all trendy, but that doesn't have to be a bad thing. KAY-lyn is the only one I actively dislike; the others I find mildly annoying at worst. I actually kind of like KAY-lee sometimes.

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How many people do you know with the names I listed above? How do you see them spelled most often?
HAY-lee, I think I've known a couple, both Hayleys.
KAY-lee, never met one, but have come across a couple in fiction, both Kayleighs.
KAY-lyn, never met one outside of BAs on this site.
KATE-lyn, have known 4 or 5, all Caitlins, apart from one who's a Caitlyn.