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This sounds almost like a Mary–marry–merry merger question! I'm from Southeastern Pennsylvania.

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1. Car category (/ɑ/)
Ariana (but would be hesitant to assume that I was pronouncing correctly for a particular person)

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2. Marry category (/æ/)
Karen
Cara/Kara
Tara
Barry
Clara

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3. Mary category (/eɪ/)
Mary
Cary

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Variable Category
Aaron (Marry, or Mary if that's the way they pronounce their name_
Ariana (Car, or any other)
Darren (Marry, or Mary)
Sarah (Mary, or Marry)
Carolyn (Marry, or Mary)
Gary (Marry, or Mary)