You won a Free Cruise, and so did Jack Dawson. The cruise was Titanic!
So it is not about what happened is good or bad. Simply because one can only tell that in retrospect. After connecting the dots. That too, the judgement will be based on the person's personal philosophy and worldview. One may say winning a Cruise ticket during a dockside poker game gave Jack an opportunity to see life, to experience love and also save Rose twice. Once when she wanted to end her life feeling helplessly trapped in the situation to marry her rich snob fiance. And at the end when the ship sinks.
Jack, who was otherwise living a loafer's life gets to dine at a first-class table on the cruise, love and dance with a society girl Rose DeWitt Bukater. For someone, who has made his living making sketches on the streets of Paris, gets a request from Rose to draw her in the nude wearing nothing but the invaluable blue diamond her fiance Cal had given her. But then, the story ends with the death of Titanic and Jack.
This is what Jack says to Rose at the end, "Winning that ticket, Rose, was the best thing that ever happened to me. It brought me to you and I am thankful for that, Rose. I am thankful. You must do me this honour, Rose. Promise me you will survive, that you won't give up, no matter what happens, no matter how hopeless. Promise me now, Rose, and never let go of that promise."
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