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Fear of authority
If a child is used to obeying others and never questions them for fear of punishment, he or she may struggle to use their own good judgement later on in life, and end up acting as he or she is 'expected' to, by reflex and from fear of disappointing or being 'punished.' This could take many different forms from breaking up with a partner to losing your friends or job.
Need for attention
Subconscious or not, over-generosity is a way of attracting attention and a sign of needing love. People who always foot the bill in restaurants or who are always on call 24/7 for their friends whenever they need them are really showing a need for love and attention.
Low self-esteem
Uncontrollable leniency with others is the sign of someone with very low self-esteem and who finds it hard to imagine others can think they are worth anything because they have no self-worth themselves. People with low self-esteem try and remedy it in the wrong way, by spoiling and kowtowing to those around them, letting them get away with anything and not being their true selves. They'll go to any lengths to achieve acceptance, but the results aren't worth it.