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No, you cannot marry Dudley. Really, you cannot marry any of the characters in Story Mode (Bust Out Mode); AKA the sims you did not create. Let me make this more clear. You cannot marry any of the sims created by the game like Dudley or Bing or Mona or Mimi or Fanny or anyone like that. So here's what you do. You go to freeplay and make your own sim, though. Make one that your character would like! Then move them into a lot with A PHONE so you can contact them. Throw a party or just wait for them to walk by your place (this place has to have the goal to marry someone!!). Then fall in love and propose.

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Q: Can you marry dudley on Sims Bustin' Out PS2?
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