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Midwesterner here: I pronounce Harry like hairy (which is why I've never seen the appeal of the name) - probably because I pronounce merry, marry, and Mary all the same as well - and Aaron and Erin sound alike to me. However, this is the first I've ever heard of Ann and Ian being pronounced the same! Ian is EE-ən, definitely two syllables.

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www.behindthename.com/pnl/69381
www.behindthename.com/pnl/69381/109399
www.behindthename.com/pnl/69381/91835
http://greens-end.myminicity.com/