To dream of a Jack-o-Lantern is an unconscious indication that you are ready and able to overcome any addictions you may be struggling with at this time. The Jack-o-Lantern is a reminder to become a witness to your thoughts surrounding the addiction, whether it is food, drugs, alcohol, sex, shopping, etc. A Jack-O-Lantern with a smile suggests that you would do well to seek help and you will emerge triumphant. A Jack-O-Lantern with a frown implies that you are doing extremely well sorting yourself out and may only need to remain strong to take victorious steps on the road to a new lifestyle.