I am sure I will be flamed for this, but I started telling ds to go to his room if he was going to cry about it. He started crying about everything at that age too. I don't think it is inappropriate to teach your child that it is unacceptable to cry about EVERYTHING. Things that genuinely make them sad or angry or scared, yes, the color of a cup, no. And it isn't because he is a boy, I would do the same for a girl. I have told him that the crying hurts my ears too and that crying about it is not going to change anything. Not because I am being harse, but because it is true: his tears and loudness are not going to get him another color cup. So if he would like to continue to cry about it, he needs to go somewhere where it won't hurt my ears until he gets control of himself. A lot of limit testing happens at this age, including the "how much will crying get me?" limit. That said, I have never forced him into his room. Generally his desire to be with me outweighs his desire to throw a fit and he calms down. Oh, also, if he can't tell me what the problem is, I ignore the crying. For example, "what's wrong?" "I want the red cup!" "Honey, I already gave you the blue cup." "But I want the red one!" "Well, I am not going to give you the red one, you can have the blue one and next time I will remember to ask you which one you want before I pour the milk in it" Followed by increasing wailing. "HOney, you can have this blue cup but you need to calm down" " I don't want to calm down!" " Then you can cry in your room until you are ready to be calm" "NO!" More wailing. After that, when it is obvious he doesn't want to compromise or he just wants to scream, I ignore it and go about my day. I don't stay in the same room, because it does hurt my ears and tends to make me feel angry, but I don't forcibly sequester him. And he calms down in about 10 minutes. For my ds, he really had no idea how to calm down and he had to learn how to do it. He was not able to listen when I tried to talk him down, talking seemed to make things worse, so I had to just leave him to his own devices. Once he is calm, not necessarily completely done crying but no longer wailing and screaming, I would always give him a big hug and talk about what had upset him. But I do not try to have that conversation while he is upset. And I try really hard not to carry any irritation around after the fact. So far it has worked well and at barely 4 yo, he doesn't cry that often. He is a person of black and white, like me, so I have been telling him a lot lately that it is okay to cry, that he doesn't have to hold it in all the time. I do not think this is my method, but rather his inability to see shades of gray. Let the flaming commence!