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Haley--quiet country gal.. cute but not gorgeous..
Hayley--talkative, and creative....loves to go to parties
Hailey--introvert..short dumpy.. wallflower
Hailee--High School cheerleader and class snob
Haylee--band geek..bookish not to friendly
Haylie--class clown friendly with everyone
Hailie--door mat everyone has had a turn

Haley--cute, fun, 3 or 4 years old.
Hayley--fun, blonde, 12 or 13.
Hailey--normal, origional, cute.
Hailee--annoying, bratty.
Haylee--Cheerleader, popular, sweet.
Haylie--Haylie Duff...(Hilary's sister) blonde
Hailie--I dislike this spelling a lot. stuck up, mean.

Haley: pretty, sweet, fun
Hayley: pretty & knows it, wealthy
Hailey: spunky, cute
Hailee: ditzy
Haylee: popular, pretty
Haylie: cute, shy
Hailie: ditzy

Haley - very sweet girl whose averagely cute & averagely smart
Hayley - average girl
Hailey - intelligent girl from smart family
Hailee - popular girl
Haylee - snobby girl
Haylie - trendy girl
Hailie - ditzy, but sweet girl

Haley: a happy-go-lucky preschooler
Hayley: I think of a young Hayley Mills, blonde and British
Hailey: a happy-go-lucky pre-teen
Hailee: a ditsy cheerleader
Haylee: perky but intelligent and popular
Haylie: country bumpkin
Hailie: happy-go-lucky African American girl

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That IS strange how different spellings evoke different images of a name. :)

Haley: average
Hayley: trendy
Hailey: good girl
Hailee: popular
Haylee: fun, unique, "out there" personality
Haylie: snobby
Hailie: little girl

Haley: intellectual girl
Hayley: average, normal girl
Hailey: ^, less than 20 years old
Hailee: trashy teen
Haylee: very trashy teen
Haylie: trendy teenager
Hailie: cute little girl