Putting one’s trust in the world instead of god; futility, not a chance Related DreamsGambling 1. To dream of winning at gambling suggests that the opposite could be true—one will lose. 2. Willingness to take a chance on everything from business to romance. 3. The dreamer is involved in some venture involving great risk.Gambling If you gamble in your dreams you are likely to be trusting to luck in everyday life. If you lose in the dream you will lose a friend.