To dream of a lollipop represents enjoying thinking it’s easy to feel special all the time. Feeling good that other people are treating you special all the time. A sense of security in feeling good getting special treatment. Enjoying being popular. Enjoying feeling special with people of the opposite sex liking you.
Negatively, dreaming about a lollipop may reflect too much confidence in how easy it is to enjoy getting special treatment all the time. Never believing you deserve anything except to feel good getting special treatment. Enjoying being mean to people while you are popular.
Lollipops in dreams are common to people thinking about or experiencing oral sex.
Example: A young man dreamed of giving his ex-girlfriend a red lollipop. In waking life he was enjoying himself making jokes about their past sex life which involved oral sex.
Example 2: A young girl dreamed of seeing tree. In waking life she was aware of herself being very confident in her popularity giving her special treatment no matter how mean she was to people less popular than her.