I had a friend ask me about dreams where your teeth are loose or falling out and I knew that I had several dreams with this theme, and have even heard references to it on shows like 30 Rock. So, let's look that one up:
"Lose a tooth and you are afraid of losing a loved one. Lose all of them and you are full of anxieties about the future." (1)
"Dreaming of teeth falling out may represent insecurity. These dreams often occur at a time of transition... When you lost your milk teeth, you also gradually lost your childhood innocence. Losing your teeth today therefore shows that today you have similar feelings of uncertainty and self-consciousness as you did in childhood. The dream could also highlight your worries about getting older or your sexual attractiveness." (2)
"Im Tofeeq, a Palestinian woman, told me that among the Arabs it is believed that if you dream of losing teeth it means your brother or son is in trouble. She had a dream in which three of her teeth fell out. The next day she received a call from America to say her son had been shot in the head three times by a gunman." (3)
In my own experience, I always had a sense of fear during these dreams that I would be ugly, so I'm guessing in my case it's insecurity about how I look. My other insecurities tend to play out in my dreams in other ways, I guess, like being chased or being in perilous situations.
(1) Grant, Russell. The Illustrated Dream Dictionary.
(2) Hamilton-Parker, Craig. Remembering & Understanding Your Dreams.
(3) Crisp, Tony. Dream Dictionary: An A to Z Guide to Understanding Your Unconscious Mind
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