It could be at a playgroup, in a restaurant or at school - your child cries at the drop of a hat. What makes some kids more sensitive than others? Kids have vastly different temperaments, and there are pros and cons for each. A stubborn child might carry that streak of independence into a self-sufficient adulthood; the shy child might become an observant, intuitive and polite adult; and the "crybaby" will likely be an empathetic adult who is highly attuned to others' feelings. But dealing with a crying child at the time makes it hard to see past the emotions he shows. After you've ruled out physical discomfort, such as being sick, tired, cold, hot or hungry - these are powerful feelings that can overwhelm small children - delve into what's going on in his head. Is he overwhelmed, overstimulated, angry, frustrated, or has he had his feelings hurt?
Barring all these things, if the child just starts the waterworks whenever he feels like it, then it's time to start trying behavior modification. Always recognize his feelings by saying something like, "I realize you're sad that we had to leave..." or "I know it's hard to come home from the store without a toy..." Then if he's still hysterical, tell him that you can't help him until he stops crying and uses his words to tell you how he feels. A crying child usually will realize that the theatrics aren't the best way to express his thoughts and eventually will let you know his needs verbally. Boys who cry a lot shouldn't feel ashamed of their emotions - bottling them up can be detrimental to their development - your sensitive son may grow up to be a man who feels safe in expressing his emotions, which is a good thing. Have respect for his emotions, but don't cater to his histrionics.