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The 2nd to last mission of Grand Theft Auto IV. In the previous mission you were given the choice to either strike up a lucrative deal with the person who screwed you over earlier in the game or take revenge for said screwing over. Which one you pick determines what happens in this mission.
If you pick "Revenge" Pegorino kills Kate shortly after you tell her you're done with your life of crime and that you may want to settle down with her.
If you pick "Deal" Roman gets shot at his own wedding and Kate breaks up with you for being a greedy jerkass.
Made even worse by the post credits phone call Niko receives:
Revenge ending: Packie phones in tears over how, in the space of a few months, two of his siblings have been murdered and one has a long prison sentence, leaving Packie with only his mother and a brother who is a drug addict or a corrupt murderer.
Deal ending: Mallorie phones Niko and tells him that, due to Roman's death, she's not only pregnant with his child, but never got the chance to tell him, and will now be forced to raise it without a father.