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Rory

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Rory Elizabeth
Rory Anna
Rory Margaret
Rory Jane
yeah

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Both Cassandra and Grace are too frilly for a girl Kelly., they make her sound like a boy. unless she is supposed to be the boyish one, in which case having a sister named Cassandra would work well.

My first thought when I saw that was Veronica. Not really into Cassie... Grace and Gracie are more of an either really old or more recent trend, so it doesn't really fit '92.

Cassie works well as a sister name for Kelly. Cassandra "Cassie" works, but I think that just Cassie would work even better.

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Kelly and Grace "Gracie" seem like completely different styles to me, but Cassandra Grace or Cassie Grace would fit with Kelly Catherine.

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Sister names:
Amanda
Samantha
Danielle
Erin - Maybe Erin Grace?
Natalie
Sabrina
Sasha
Lindsay / Lindsey
Courtney
Erica
Heather
Amy
April
Stephanie
Jillian / Gillian
Rebecca
Rachel
Sarah / Sara
Amber
Alexandra
Melissa
Brooke
Bethany
Megan / Meghan
Valerie
Sierra
Kirsten
Kristen
Krista / Christa
Christy / Kristy
Christine
Christina / Kristina
Summer
Tara
Tammy
Aubrey
Jocelyn
Vanessa
Alyssa

Grace doesn't strike me as particularly 1992-esque. In 1992, it was 127.

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Kelly and Sarah
Kelly and Amanda
Kelly and Megan
Kelly and Lauren
Kelly and Emily

Kelly Catherine & Erin Grace

My first thought was Rose, probably because I know a Kelly Rose.
Kelly & Cassie would sort of work, but Cassandra is too long IMO. I think Kelly and Grace "Gracie" is best.

What about Jessica 'Jessie' or Jennifer 'Jenny'?