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I like it only because of the associations with cute British actors -- Rupert Everett, Rupert Graves, Rupert Friend, and Rupert Grint. :)
I can't imagine ever naming a kid this (would I call him Ru? Rupie? lol) but maybe a dog or cat. :b

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~Heather~
"Why is it that, as a culture, we are more comfortable seeing two men holding guns than holding hands?" - Ernest Gaines
"When the power of love overcomes the love of power, then the world will know peace" - Jimi Hendrix

I like it with the nn Rudy. I also like it

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Rupert is adorable on a little boy and handsome on an older one. It's a great classic, yet is not overused like David Matthew and Andrew.

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Top Names
Marguerite Ruth , Eleanor Colette, Evangeline Fae, Lucine Mariana, Celia Rosalie
Ezekiel Zane, Asher Taliesin, Sebastian Ainslie, Arthur Isidore, Hector Elisha, Diederik Ariel, Dashiell Benedict, Costanzo Leonti

You have wonderful taste. Simon, Thomas and Rupert are terrific. Rupert is a little more quirky than the other two, but it's still a classic and deserves more attention than it gets.

Stick with Simon and Thomas? I'm sorry but Rupert really rubs the wrong way with me. I can't see it as an attractive name. The others however are beautiful.

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Loving wife to Jack
Daughter to Paddy and Cait
Sister to Finn, Con and Muirgen
Mummy to Isaac, Oliver, Jay, Beth, William, Alexandria, Ruby, Lucas and ONE-ON-THE-WAY!!!
Fur Mama to Belle, Jasmine, Minx, Monster, Mischa, Kitty, Hugo, Cleo and Darcy

I love Simon and Thomas, not crazy about Rupert...and not sure it fits with the other two.

Well, to be honest but kind =) I really don't like the name that much. I like your other two though!

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I will lift up mine eyes unto the hills, from whence cometh my help. My help cometh from the Lord, which made heaven and earth.

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Psalm 121:1-2