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Separation Anxiety
When Your Child's Afraid to Leave Your Side
By Elizabeth Pantley, author of Perfect Parenting, and Kid Cooperation
Acknowledge his feelings, and help him understand them. Then reassure him and help him deal with the feelings and learn to get by them. "I can see you're a bit nervous about joining the party. That's okay. Take your time and let's see who you know. There's David! Why don't you go over and show him your new watch?" 
Take away the mystery:Talk about the event in advance. Let your child know what to expect, how long he'll be there, what he'll do and when you'll be back to pick him up. Information like this will help your child feel more comfortable about your separation.
Give your child choices: "You've been invited to sleep over at Brandon's house Friday. He's really excited. He said you'd go roller-skating and then make homemade pizza. Do you think you'd enjoy that?" Ask your child helpful questions to see why he doesn't want to go. Perhaps there's something specific that would help him be more comfortable, maybe knowing that he can call you to pick him up if he changes his mind. Your child may not be comfortable and choose not to go. That's okay. There will be many opportunities for your child to spend time with a friend. Some more tentative children will pass on an invitation and be comfortable with their decision. Typically, given enough time, the child will outgrow this separation anxiety.