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Rupert Giles & Jenny Calendar (Janna)

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The Watcher and the Gypsy fell in love.  Unfortuanately, the Gypsy was killed by the Evil Vampire.

Jenny Calendar was actually a gypsy sent by her clan to see that Buffy Summers and the vampire Angel didn't get too close.  Though Giles was upset about that and Jenny was upset when she found out about Rupert "Ripper" Giles' past, things were starting to come together... until Jenny was killed by Angelus.  Giles was, understandably, upset...