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Penelope was actually unseen throughout the entire first game she "appeared" in, Hugo's House of Horrors. In that game, Penelope was kidnapped by ghouls who called her to their haunted house claiming a babysitting job was waiting for her there. When Hugo finally reaches the cell where she's being kept, she is just a silhouette against the window, and the game immediately cuts to the day of their wedding, when both of them are depicted as (much more detailed) silhouettes.
It was only with the release of the sequel, Whodunit?, that Penelope was actually revealed. In that same game, Penelope replaced Hugo in the starring role; newlyweds Hugo and Penelope visit her uncle Horace before intending to set out on their honeymoon, but while Penelope is taking a nap, Hugo disappears into a secret passage, and upon waking, Penelope discovers that she is locked in the room, peeking through the keyhole just in time to witness Horace's murder. Penelope must search Horace's sprawling mansion and the grounds surrounding it in order to find her missing husband and solve her uncle's murder.
In the third game, Jungle of Doom, Penelope returned to damsel-in-distress status. After leaving on their honeymoon, Hugo and Penelope's plane breaks down and they are forced to make a crash landing in the middle of a jungle. Seconds after leaving the plane, Penelope is bitten by a deadly spider. A tribe of natives lies near the campsite, and the medicine man informs Hugo that the only thing that can save her life now is the mystical waters of a magical spring of life, hidden somewhere in the jungle. At the end of the game, Hugo and a revived Penelope repair their plane and fly off together into the sunset. No games have been set after Jungle of Doom, so it can be assumed they finally got their Happily Ever After.
The fourth and final Hugo game, Nitemare 3-D, was a first-person-shooter based on Hugo's House of Horrors. Just as in the original game, Penelope is kidnapped by ghouls, but unlike the original game, Hugo sets forth to get her back not by benignly solving puzzles, but by picking up a gun and wasting any monsters foolish enough to come between him and his true love.